For all who have had the pleasure of strolling along Chestertown's ancient High Street,
or enjoying its spacious sidewalks lined with tidy brick buildings varied here and there
with interesting frame structures - there must inevitably arise the question, how did such
a pleasant, workable, and utterly humane plan for town life come into being?
The seat of the Eastern Shore's oldest county Kent was finally put at its present
location on the Chester River in 1706. Beginning with a Governor's proclamation in 1668,
there had been intermittent proposals to establish a colonial port at about this spot on
the river. Doubtless the building of a county court house on the present grounds by 1697
all but assured the founding of the town. Faulty provisions for the sale of the land and
other setbacks caused the Legislature in 1730 to order a careful surveying of the Town's
100 acres and the laying out of the logical and functional plan which we continue to enjoy
to this day.
A broad main street (called High, platted at 90 feet wide) takes one from the River to
the chief public space, situated at the intersection of a crossing street (called Cross,
platted at 66 feet wide), where the places of public business and other amenities are
located. The simplicity of this scheme (somewhat like a miniaturized Philadelphia) is
something of a rarity among Chesapeake ports. Other Chesapeake harbors, like Annapolis and
Oxford, being closer to the Bay itself, have too uneven a coastline or irregular a terrain
to permit a clear crossplan with neat rectangular subdivisions.
Besides its court house, the development of Chestertown during the 18th century owed a
great deal to its being designated a Port of Entry, becoming an educational center
(especially with the founding of Washington College in 1782) and its being a trading
center for the vital agricultural industry of the county. The economy down to 1760 had
been highly dependent on tobacco, but a dramatic shift in the direction of wheat
production brought about a new prosperity that resulted in increased population for the
Town and significant new ties with Philadelphia in the period just preceding the
After a post-Revolutionary period of decline and relative stagnation, the Town's
fortunes clearly began to rise again by 1860, the time when the existing Court House was
built. Census figures from 1860 to 1900 show a doubling of the population (to 3008, about
300 people fewer than the present-day count). Fruit growing and the coming of the railroad
to Town in 1872 partially account for this small boom, which in turn helps explain the
large number of buildings remaining from that period. The 20th century has seen modest
growth within the town limits with little architectural change in the Historic District
since the reconstruction of a commercial block, destroyed by fire in 1910. Rather, the
approach of recent generations has been to preserve the old or to add and replace in
architectural styles compatible with the Town's past.
The modern-day visitor will probably be aware that the Town's physical aspect has been
noticeably affected by the disappearance of the commercial wharves that once served sail
and steam boats in their trade with the outside world. Less obvious perhaps are the
changes undergone within the public space at the center of Town. Where there is now a
delightful park with its ornate fountain, there stood until the 1890's a solidly built
market house, the armory, and the first engine house for the volunteer fire department.
The public area around Emmanuel Episcopal Church underwent less drastic change; but it is
worth noting that the building of the 1860 court house led not only to the demolition of
the clerk's office and the removal of the church cemetery, but to a new and much larger
jail (1884) and the development of the row of tiny-scaled lawyer's offices along Court
Street. Little realized is the fact that the 18th-century court house formerly faced this
street, rather than High, thus explaining the unexpected stateliness of the Geddes-Piper
house on nearby Church Alley.
To understand the past appearance of Chestertown's civic center, one must also imagine
a grouping of commercial taverns, inns, and hotels around the perimeter; and, just as
importantly, a rectangle of open space, 160 feet wide, extending from Court Street to
Spring Avenue. An unmistakable axis had been gradually established by the long front of
Emmanuel Church, and the later placement of the first Methodist meeting house and the
Masonic temple. This provided a northern boundary for an open area which could be used for
all sorts of activities: everyday, festive or solemn.
The range of architectural styles to be covered in this brief guide will begin with the
"Georgian," so called because this orderly style was favored in the English
speaking world during the reigns of the successive kings of that name. In conservative
Chestertown, the style remained popular until at least 1830 and it was revived by 1900.
The quality of the workmanship in several Chestertown buildings from just before and after
the Revolution is notable. The all-header bond brickwork in some important structures
(frequently just the facades) was, for example, costly and difficult to execute. Only
Annapolis has more buildings in this technique, but this possible close link with the
capital city is counter balanced during the Georgian period by clear connections with
Philadelphia. Chestertown's largest Georgian building, Washington College, was built by
Philadelphia workmen in the 1780's. On the other hand, there must have been good, purely
local talent at about this time, for we know of four silversmiths during the 1770's.The
romantic movement begins to affect local architecture only by the 1840's, and, it would
seem, very conservatively at first. There is little evidence of Downing's version of
American Gothic and little to represent the Greek Revival, Very popular by mid-century,
however, was the Italianate, or bracketed villa, style. A host of subdued examples of this
type of building will be found, both public and private, until the 1870's and 80's when
various extreme forms of Gothic or "Queen Anne" make their appearance. Often
associated with Queen Victoria's reign, these styles had contemporary vogue in England,
and were made possible in Chestertown partly because many of the constituent parts could
be ordered ready-made from Baltimore.
All the same, some of the best of the Town's high style architecture dates from this
period with no little of the credit due to local builders, like Walter T. Pippin, H. M.
Stuart and A. M. Culp. Another popular late l9th century style was the French-inspired
Second Empire, seen most impressively in Stam's Hall, one of the Town's best-loved
structures. With his house on Washington Avenue, Stam also initiated an expansion of the
Town in the direction of the College, that has continued unabated down to our own time.
The architectural flair of his own buildings has been reined in considerably since his
day, as the beginning of the new century brought more and more conservatism of style and
detail. The bungalow of the 1920's represented something of an innovation, but, by and
large, the architecture of the 20th century within the Town's Historic District has
maintained a sense of continuity with the Town's past. It is perhaps for this reason that
visitors and townsmen alike find the place so harmonious and livable today.
This guide presents a sampling of highlights from all eras of Chestertown's
architecture. Not every building of merit could be included. The thought has been that a
visitor with little time might explore one or two of the four sectors into which the
District has been subdivided, leaving for another occasion the viewing of the rest. It is
to be hoped that visitors, no matter what length their stay, will recognize that the
architectural heritage of the Town is proudly cherished by its citizenry.
Robert J.H. Janson-La Palme Chairman, Historic District
Map of Chestertown's Historic District
1. This handsome 18th-century brick building signalizes
Chestertown's importance as a Port of Entry for Maryland's Eastern Shore, one of just six
in the colony created by the Maryland General Assembly under pressure from the Crown in
1706. Early buildings of this type and size have all but disappeared from the original 13
colonies. The principal block facing Water Street (originally Front) Street was
constructed in the 1740's by Samuel Massey and features Flemish bond brickwork with glazed
headers. The prestigious Ringgold family took over the building in the latter part of the
18th century and is presumed responsible for the two-bay addition that is easily detected
along the landing front. Although the front porch is a recent reconstruction based on the
discovery of footings and other evidence, the porch facing the river is modern. The Custom
House has been in private hands for many generations and has been gradually restored in
recent years. The graceful front portico is the design of restoration consultant Michael
Bourne and uses motifs of the area. This historic building was very important to the
establishment of the Town's National Landmark District. Chestertown had a "tea
party" in May, 1774, not far away, when a band of angry citizens attacked the cargo
aboard the brigantine belonging to Custom Collector William Geddes.
2.A splendid example of the Italianate style that was widely popular in the region,
James Taylor built this river-front mansion in 1857. Scrupulously restored, this house
retains its finely detailed lantern on its, typically, low-pitched roof and displays a
rich series of ornamental brackets under the eaves of both main roof and porches. Fine too
are the jig-saw cut porch balustrades and the general proportioning of the building. Key
to the appreciation of this type of house design is the combination of symmetry and an
open, airy feeling.
3.This impressive brick residence has dominated an important waterfront Street corner
for more than two centuries. The compact massing of its all-header and Flemish bond brick
walls, hipped roof and Greek Revival style portico stands in marked contrast with #2. The
L-shaped structure seems to have been put together in stages with the Water Street block
having been built shortly after 1743 by Dr. William Murray.
Thomas Ringgold, wealthy merchant and Maryland legislator, remodeled and greatly extended
this main block after acquiring it in 1767, installing a beautiful paneled parlor in the
front section (dated 1771, attributed to the Annapolis designer and woodcarver William
Buckland and now transferred to the Baltimore Museum of Art) while putting in a grand
staircase to the rear. The fact that only the garden side wall of the entire rear wing is
in all-header bond tends to support consultant Michael Bourne's contention that all of the
structure at the back is from Ringgold's time. Had there been a preexisting mid-century
house to be incorporated, as has been frequently surmised, the costly all-header bond
would have been used, almost certainly, in a Cannon Street entrance wall. Besides
Ringgold, there have been many other important residents, such as United States Senator
James Alfred Pearce, and, more recently, the presidents of Washington College (which now
owns and maintains the building). The Hynson-Ringgold House, as it is now called,
possesses in addition to its large walled garden a spacious open lot in front which
affords an unbroken vista of the Chester River.
imposing Georgian style house enjoys an excellent site at the foot of High Street. it has
thus been the residence of locally prominent families, especially the civically active
Wickes. Construction was initiated by the Wallis family, and the clean four-square Flemish
brick construction fits the generation of building just prior to the Revolution.
Subsequent owners added subsidiary buildings at left and perhaps one at right (both now
destroyed) and a large garden extending to the rear. The doorway too is of later
well-restored house presents, at first, the appearance of an 1880's three-bay frame
dwelling complete with nicely detailed front porch, slender corner pilasters and a bay
window for the parlor. There is evidence of late 18th-century ownership of the 2 ½
-storey section, however, which suggests that, like many other house owners during the
relatively prosperous 1880's, John Hines sought a more fashionable facade for his old
6.& 7. Originally a five-bay single residence, possibly built as early as
ca. 1743, this building was widened in the early 19th century into a two family home. The
break in the brickwork, which in the earlier part is Flemish bond with glazed headers,
makes the addition apparent. Noticeable also is the jog of the water table above the
basement windows in the older section. The building has been well cared for in recent
years and the comfortable front porches appear to be comparatively modern.
8.A small-scale frame survivor from the second quarter of the 18th
century, this building delights because of the contrast between the rigidly symmetrical
first floor and the uneven arrangement of the second-storey windows. The front wall has
beaded clapboard siding, but the end gables are of brick to accommodate the chimneys. The
entrance porch was designed by architect James Wollon at the time the structure was
restored by the Maryland Historical Trust.
a double residence, this five-bay house was originally constructed for John Lorain, ca.
1776-1796. The facade arrangement is, therefore, more thoroughly symmetrical than the
earlier #8; but, like it, there are two brick end gables framing a front wall of wood. The
front porches are from some time in the last century.
10.Built in mid-19th century by Thomas Hynson, this building is in a simplified
Italianate style. It retains part of a tell-tale lantern atop its low hipped roof, has a
bracketed cornice, and walls of hard brick with fine mortar joints. The large
ground-storey windows can be explained by the fact that the old retail district of the
Town began at about this point on High Street and that there was definitely a shop here in
the later 19th century, probably even from the very beginning.
11. Constructed by the Buck family ca. 1735-50, this building has undergone
extensive restoration thanks to Preservation, Inc., a local group, and the Maryland
Historical Trust. Like its later counterpart across the street, this brick structure is
known to have served as a store, at least in its later life (1854-1922) when in the hands
of the Bacchus family. Important in the restoration were: the raising of the roof lines
according to evidence uncovered by Michael Bourne, restoration consultant; the reopening
of a Queen Street entrance; the relocation of the High Street door; and the design of
appropriate doorsteps. A clumsy early 19th-century addition at the right of the High
Street front has been appropriately kept, but its common bond brickwork contrasts with the
Flemish bond wall, irregular string courses and fieldstone foundation of the early
construction. The building serves in part as a small local museum.
12.The Imperial Hotel was erected in 1903 by W. W. Hubbard for use as office and store
as well as a place of lodging. The double tiered verandah offers a pleasant aspect from
the street and has shaded and sheltered many a passerby on the walk below. The entire
building has been renovated for use as a hotel with the harmonious addition of an entrance
court at the rear (visible from Queen Street) that includes a rustic outbuilding designed
by local architect Marsha Fritz.
13.The Chester Theater opened in 1928 as the New Lyceum. It supplemented Stam's Hall,
which became known as the Old Lyceum, as a place of public entertainment. The yellow brick
in the front of this building is unusual for the town, though fashionable architects began
to use this color by the 1890's elsewhere. Like #23, the street-level doorways are
clustered together and placed within a wide frame of bricks in parallel rows. Similarly,
there is also the use of a checkerboard pattern of brick in conjunction with the
second-storey window arches. Although the ground-storey bricks have been painted, much of
the roof and marquee treatment appears to be original.
14.A Chestertown druggist/merchant, Colin Stam, undertook this large and ambitiously
designed building in 1886 to house his flourishing business on the ground floor and
provide spaces for public entertainment and gatherings on the second and third floors. The
people of the town contributed S1,000 to pay for a bell in the tower, which still tolls
the hours. The structure is in the Second Empire or Beaux Arts style, that was widely
popular during the 1870's and '80's for civic buildings. The Stam building is remarkably
elaborate for a town of about 2400 people, with its varied brickwork, white painted metal
cornices, sandstone details and multi-level Mansard roofs. The doorway and window
treatments at ground level no longer adhere to the original design but the building is
15.A low-pitched hip roof on this two-storey wooden commercial building built by the
Spencers reminds one of #10 across the street. Long neglected, this prize example of a
retail establishment, which must date to some time prior to 1877, has been beautifully
painted and its cornice and brackets restored. The projecting display windows are among a
very few originals that still survive in the town.
16.This impressive bank was carried out in a neoclassic style, so popular from the
1820's onwards, expressing timeless strength in architecture. Built in 1929, amid some
furore because It replaced a large 18th-century brick building at this location, the
result is quite successful and untouched by later modernization. The entire facade is of
sandstone and suggests a temple front in the Ionic order. The inset carvings of swags
mid-way up this monumental facade reveal that the architect was softening the effect a
little by introducing a device popular with French neo-classicists.
17.A restoration program of major proportions was accomplished with private funds in
the late 1970's when the old tavern building, called the White Swan, reemerged after
generations of abuse and neglect. An archaeological excavation yielded some 70,000
objects from around the site, and the beauty of the Flemish bond brickwork with glazed
headers was brought back to life. Having been built by Joseph Nicholson about the middle
of the 18th century, this rare surviving tavern is said to have provided refreshment to
George Washington himself on one of his visits to the Town. Michael Bourne, the
restoration consultant, removed some later dormers, corrected the design of the full-width
porch and moved back the old kitchen building at the rear.
In another phase of the plan to convert the White Swan into an inn, the building next
door at High Street, an 1895 drug store, was also restored to its proper appearance at
ground level while the second-storey space was linked to the White Swan to form a large
18.Cross Street south to the railroad tracks has been largely a commercial area for a
very long period. This is one of the shops whose occupants changed with some frequency and
has been in existence for perhaps a century. A recent partial restoration revealed many
internal changes and the covering up of a curious set of second-storey "jib
doors" above the display windows. Now presenting an attractive appearance, this
property was the subject of a legal suit between the former owners and the Town. The
Historic District Commission had insisted that all modifications to the structure be
applied for. In supporting the correctness of the Commission's position, the Maryland
Court of Appeals in 1981 upheld the wording of the Town's Ordinance as intelligible to the
layman and pointed out the Commission's right to consider the effect that a building may
have upon the general "streetscape". This Chestertown case has drawn national
attention and encouraged preservation commissions elsewhere.
19.Constructed between 1908 and 1909, this was the Town's first sizeable volunteer
firehouse. By the 1890's there was talk of upgrading the primitive engine house located
near the market building on High Street. The style chosen was a severely geometrical one.
The bell tower, subsequently removed, hasrecently been put back during a fine job of
adaptive reuse of the building carried out by Annapolis architect, James W. Burch.
Ironically, the firehouse was no sooner built than Chestertown suffered its worst general
fire. The entire commercial block on the other side of Cross Street was destroyed in 1910.
20.The railroad began to play an important role in the economy of the town in 1872, the
line extending all the way down to the Chester River wharves. This surviving passenger
station, which has been moved from the foot of Cross Street to allow for improvement of
the thoroughfare, still provides a charming reminder of days gone by. Built ca. 1905 in a
popular timber and stucco style that is admirably suited for the provision of wide
sheltering eaves, the station is one of the few of this style remaining on the Delmarva
21. Originally built as a church in 1859, this edifice has spent most of its life in
secular uses. The Methodist Protestants of Chestertown broke away from the main body of
the church by 1830 and at first used a very simple building. Their new brick, temple-like
structure of 1859 had, when still a church, tall windows along the flanks and a sanctuary
(still visible) at the rear. After the congregation moved to High Street some thirty years
later, the building became part of the adjacent public school buildings; and, finally,
since around the turn of the century it has housed various printing operations. Although
the flat vertical pilasters and the cornice around the building hint at the fading Greek
Revival style, the heavy bracketing under the roof points to the later mid-century period.
22.The cornerstone for Janes M. E. Church had only just been laid in 1914 when the
twin-towered, Gothic style 1860's building belonging to the congregation on South Queen
Street went up in flames. The church is named after Bishop Edmund S. Janes in response to
his appreciation of this black congregation's work in Chestertown. This building,
constructed of hand-made bricks, represents also the congregation's continued appreciation
of the Gothic style - the style still visible at this date in both Christ Methodist and
First Methodist over on High Street. The church has a well finished interior and remains
23.This nicely proportioned three-storey building is one of a number needed to replace
the losses that this commercial block suffered in the great 1910 fire. its tidy
brick-faced facade seems to combine two style trends of the 'teens and 'twenties: the
"Prairie" and Renaissance-revival styles. The simple band of rectilinear windows
at top and the wide frame rectangle of the ground storey fit the "Prairie",
while the subdivided arched window of the middle storey is in the Renaissance mode. The
short tile roof over the entrance is a later addition.
24.The detailing of the roof zone in this delightful structure suggests that the
builder had in mind that the facade would face all those approaching the business district
via Spring Avenue. Its eye-catching steeple, triangular windows, stained glass, fish-scale
shingles, etc., all fit the exuberance of the late 19th-century Queen Anne style. Below
the cornice line, however, the building has been refaced; and a Colonial Revival frame,
complete with broken pediment, surrounds the display window and doorway. This building
must have been at the outer edge of the 1910 conflagration.
25.This frame house represents in reduced scale the Italianate style of residence, as
seen at #2. It was constructed by local carpenter William D. Smith and shows the familiar
bracketed cornice (with corner pendants), heavy hoods above the windows, and a full-width
porch that has unfortunately lost some of its detailing. The house once had an outdoor
kitchen at the rear of its larger back addition. The paint scheme has now been restored to
one popular in the mid-19th century at the time the house was built.
26.This is the only remaining so-called "telescope" house in town. This type
of additive construction can even be found in some of the grander residences of the
Eastern Shore. The late eighteenth-century part is a storey-and-a-half, has beaded
clapboarding and some of its original panes of glass. The taller section was added some
time in the nineteenth-century before 1877 and shared the large chimney that was on one
end of the middle section. Here a change in type of clapboarding, dormers and other
details can be discerned.
27.A charming, small-scale tradesman's house, nicely restored and datable to 1771-1783.
Its two end-chimneys are sheathed in clapboard except at the bottom. Added living space
was achieved with two rear additions to this building, which has been facetiously referred
to as Sterling's Castle.
28.Something of an isolated survivor in this street, this five-bay brick house has a
history going back to the second quarter of the 18th century when it seems to have been
built by a member of the Ringgold family. The structure has undergone a slow but
worthwhile restoration and one can see around to the side an early lean-to addition, known
locally as a "catslide" roof.
29.Despite the wide based appeal of the Gothic Revival style in America from the 1830's
onwards, very few examples can be found today in the Historic District. Fittingly, the
finest is an excellent church, designed by Baltimore architect Benjamin Buck Owens in
1887, and constructed at a cost of about $29,000. The prospering Methodist Protestant
congregation moved here from its Cross Street building in the following year to enjoy one
of the most richly ornamented buildings ever constructed in the Town. The irregular
composition is dominated by a multi-staged tower with pointed steeple, placed midway
against the building. A lower polygonal turret is close to the street on the other side of
the edifice. Gothic arches, stained glass and buttresses are found all around. The
textures of brick, stone and slate are well handled in a building which might also be
called "High Victorian". Strangely, the rear section of Christ Methodist, now
visible, was long hidden from view by a preexisting adjacent building at the corner of
30.The tall bay window and gable-end of this residence echo some of the features of the
nearly contemporary church alongside. A long L-shaped porch fits well into the deep narrow
lot. Now in a good state of repair, the Historic District Commission played a role in
saving this building, much to the satisfaction of all involved.
31. This is one of a few surviving large-scale houses remaining on this side of High
Street just above the Market Space. Built in 1877 in a rather conservative style for
Thomas Hubbard, the facade is in five parts and absolutely symmetrical; and much of the
detail, like the bracketed eaves and hooded windows had been in use for some decades. The
ironwork atop the hip roof and the Eastlake style decoration of the porch columns give it
an up-to-date appearance. Doubtless a more varied color scheme once set off this solid
32.This building was erected in 1901 as the public school and is a prime, early example
of Colonial Revival in one of the Town's public buildings. The mass of the structure is
emphasized by the entrance tower, a high gambrel roof, and a pair of large dormer windows
(likewise gambrel roofed). The tower originally had two more stages; a balustrade,
surmounted by an open cupola. Typical of early Colonial Revival is the use to excess of
motifs like the Palladian window (in the tower and two dormers), expensive Flemish bond,
and stone trim. on this site once stood one of the most imposing mansions of the Town,
United States Senator George Vickers' three-storey Italianate residence that faced Mill
33.The cornerstone of the present U.S. Post Office was laid in 1935 after the removal
of a large, but nondescript old commercial hotel. The new structure, designed by the
Baltimore firm of Lucius White and Henry Perring, is a striking example of Federal Revival
architecture. Bearing a resemblance to such a mansion as "Homewood" (1803) still
in Baltimore, the Post Office features a tall single-storey effect, with inset panels in
the wall above the windows, and, above all, an elegant portico of slender columns with
exquisite detailing above the doorway. Buildings of this elegance were not financially
feasible in early 19th-century Chestertown. The local post office had had many locations,
the last being Stam's Hall, before this building was erected.
34.This Methodist meeting house was put up between 1801-03 after a commission of the
State Legislature granted the congregation a small portion of the western end of the
Market Space. The brick structure resembles, in somewhat simplified form, the appearance
of the earlier Emmanuel Protestant Episcopal church situated to the east of the market
Space; and the two are topographically aligned. There was originally a single main door,
facing High Street, and another smaller one on Club Lane (now Spring Avenue). It Is in
Flemish bond brick and its original main doorway seems to have been more understated than
the present one. The first American Methodist Bishop, Francis Asbury, preached here and
the success of Methodism was such that other congregations arose in Town and this building
became inadequate for the main group. It was abandoned to a variety of public and
commercial purposes when the new house of worship was built further up on the same side of
High Street in 1877,
35.Probably built by William Slubey, local merchant, in the late 18th or early 19th
century, this building is the oldest along Park Row, facing the old Market Space. Beneath
later coverings and modifications one can visualize one of the few remaining five-bay, 2
1/2-storey clapboard dwellings in town. Two lots to the rear off Spring Avenue, there
stands an original, early, small brick smoke-house, belonging to another property.
36.The old tavern and restaurant, known as the Rockwell House (probably after the
mid-nineteenth century owner) appears today to be a building of the immediate pre-Civil
War era. Its narrow block-like form carries a low metal roof, clapboard siding (beneath
the asbestos), and modest corner and window treatments, details that indicate the
lingering popularity of Italianate design.
37.Emmanuel Church is almost literally the physical cornerstone of the Chestertown
plan, and it is in this building that an important new spiritual cornerstone was laid. In
1780 a small group of Anglican clergymen met in the 8-year-old building to coin a new
title which would signify the break with England: The Protestant Episcopal Church. That
term has, of course, been in use ever since. The structure has undergone much modification
from its original 2-storey, 5-bay format. The building was entered on the long side facing
High Street and above the door was a costly Palladian window. The wall was in all-header
bond. The Georgian effects were changed in the 1880's when the sanctuary was moved to the
southeast (short) end, and the entrance shifted to the northwest end opposite. The pitch
of the roof was changed, in keeping with a more medieval look; and the windows of the
former entrance wall became single tall openings filled with stained glass. An entrance
tower and parish hall improvements were effected in 1905. Among the many famous rectors of
this church was Dr. William Smith, former Provost of the College of Philadelphia and
founder of Washington College.
38.one of the most important acts in establishing a port of Chestertown in 1706 was the
provision for a court house. The earliest known plat of the town shows the 18th-century,
apsidal-ended court house in the center of a large area of public ground with Emmanuel
Church in one corner and the cemetery or church yard using much of the rest. A small jail
stood behind the court house, the latter being of about the same size as the church in the
late eighteenth century. The front section of the present court house was built in 1860,
using a T-shaped plan whose main axis faces High Street. This, the oldest surviving part,
is in essentially Italianate style, solidly built of hard, dark brick, with typically low
roof, wide eaves, and elongated brackets along the cornice and on the doorframe. With the
cemetery gone and the need for interior space pressing, a Colonial Revival addition was
attached to the rear, with access from Cross Street, in 1969.
39.In 1826 the Maryland General Assembly granted this small lot on the public land to
the Masons and by 1835 the Masonic temple is referred to in a deed. The construction was
of a very simple and consistent sort, resembling the two churches already on this axis,
with the exception of the wide cross gable that breaks into the roof line above the main
entrance. Undoubtedly, this once contained a circular window that has since been blocked
off. The Masons had a fine hall on the second Storey, but as early as 1849 this was
abandoned to a newspaper establishment. The structure was known for decades as the Kent News building while many other offices and enterprises operated on the ground Storey. A
one-storey clapboard addition was put on, perhaps as early as 1877, to accommodate the
demand for this central location.
40.Nineteenth-century accounts refer to lawyers' offices in the area of the Market
Space and all around the Court House, but by mid-century there was a movement to create a
series of small street-side offices along Court Street for legal practitioners.
Chestertown's Lawyer's Row is an excellent example of this tendency in small-town county
seats. The street is quiet and tree-shaded, and several examples, such as this, are in
beautiful condition. This office, like its next-door neighbor at No. 115, was built in the
third quarter of the century. Its tall entrance wall suggests a dignified chamber for
consultation within. The hooded windows and the ornate pendant-brackets imply a certain
restrained richness of taste, especially as compared with the more sparsely decorated
cornice and doorway of the slightly earlier office at No. 115.
41.Like #40, this office is entered at the right. From the fact that it first appears
on an 1885 map, we may gather that it was only recently built. Perhaps the most satisfying
example of its type, one finds here a severe, dark, hard brick with thin tinted mortar
joints, a formalizing pilaster effect at the two corners, and nicely related wood and
tilted-brick friezes completing the top of the composition. The original dark door
completes the authentic feeling of this office facade.
42.This small building was one of a few such on the north side of Church Street, or
Alley, at the end of the 19th century. It has been neatly restored at ground level to its
former appearance as a small shop (though it is now an office). A "catslide"
roof can be seen around to the rear.
43.This impressive 31/2-storey 18th-century brick building comes as a surprise in its
cramped location on little Church Alley. In fact, the plot of land around the house was
entirely open between Court and Queen Streets down to the late 19th century, and the
18th-century court house faced this street. It is assumed that a bricklayer, James Moore,
began the work in the second quarter of the 18th century after acquiring the land. But the
main portion of this tall, solidly built townhouse seems to have been erected under the
ownership of James Piper in the 1780's when full three-storey elevations were common in
Atlantic coastal towns. The present form of the house with its rear wing resembles in some
respects the Powel House in Philadelphia. All four corners of the structure are framed
with unusual brick pilasters that taper at the top under the two heavy cornices which cap
the front and back of the house. The tall double chimneys must have been especially
impressive when the Queen Street side was open to view. Because Collector of Customs
William Geddes (see #1) once lived here, the building is known as the Geddes Piper House.
It is the headquarters of the Historical Society of Kent County, which bought and restored
the property, using Henry Powell Hopkins, architect, to design the rather heavy Tuscan
44.This block of Queen Street features a great variety of smaller but comfortable
residences, some of considerable antiquity. This frame house presents a mirror image of
#46, for both were constructed by William Vannort ca. 1877 on small lots alongside #45.
These houses retain their ground-storey front porches, which have now been stripped away
from so many other houses of the era. The facades are nicely framed by slender pilasters
and bracketed cornices, and the detailingaround windows and doorway reflects the continued popularity of Italianate design.
45.This small brick house may be the oldest on the street, the construction for the
Buck family probably dating ca. 1735-1750. It is of Flemish bond, has a belt course
between floors, and is notable for the irregular arrangement of window and door openings.
The rear section of the roof slopes less abruptly, giving the "catslide" effect
found in other early houses where additional space was added at the back.46.See the description for #44.
47.This common bond brick residence was built on the front of a ca. 1740 smaller house,
whose original kitchen still remains in the basement. Local attorney Benjamin Chambers had
the home built for his more famous son, Senator Chambers (see #65), in the 1780's. The
construction resulted in a high front basement and taller lines for this three-bay, 2 ½
-storey structure. The building served as the rectory for Emmanuel Church during the later
48.Of similar size and three-bay construction to #47, this house has the distinction of
being associated with the Nicholson family, prominent in the Navy during the Revolutionary
War period. The owner, John, served on several vessels and was ultimately Commander of the
Continental sloop Hornet. Brother James was head of the Maryland Navy and then head
of the Continental Navy from October 1776 until 1785. A third brother, Samuel, held
several commands culminating in the 1790's when he not only commanded the U.S. Navy's Constitution but supervised its construction.This 1780's house has architrave blocks over the windows and a brick dentil cornice. It
was expanded by 1885 to include a dining and kitchen wing at the left, and the doorway
detail seems to date from that epoch.
49.This 1770's brick house was extensively modified at the beginning of this century. A
thorough restoration has removed most of the accretions, such as the lengthy verandah,
porte-cochere, etc. The essentially simple house, built for Dr. William Houston in Flemish
bond, has thus reemerged. The dormers are of a later time, however, and the brickwork at
the left front suggests that the house was enlarged from three to five bays at an early
50.Severely abused in our century, the John Greenwood house of ca. 1867 represents yet
another example of the long-lived popularity of simplified Italianate design in
Chestertown. The house had a wing at the rear-left by 1877; and when Preservation, Inc.,
decided at great cost to rehabilitate this house, which had been all but gutted by fire,
the decision was made to attach a modern rear wing at the same point. The fabric of the
main block is essentially new but recreates charmingly the original effect. A small
balustrade above the roof and a colorful paint scheme dress up this clapboard residence.
51. This commodious house was erected by A. M. and W. S. Culp in 1896 at a cost of
$3,800. It was the second parsonage for Christ Methodist Protestant Church to be put on
this site and contains elements, like the polygonal turret above the entrance, and the
stained glass, which remind us of the church. This is, however, a very subdued late
19th-century version of Gothic. The color scheme is now appropriate to the
52.The capable and active local builder, Horace M. Stuart, constructed this modestly
priced frame house around 1880. It presents to the passerby on Maple Avenue a wonderfully
decorative, cut-out verge board under the eaves of the roof. This Gothic-inspired detail
was picked up in the front porch decoration (now lost), the bay window, and the familiar
bracketed cornice. The tall proportions of the house suggest grandness for the size of the
lot and are likewise inspired by the Gothic trend.
53.Built by William Burchinal, member of a prominent merchant family, this is a larger
and approximately contemporary version of #50. Even though on an exposed corner, it is
only the facade that is kept in strict five-bay symmetry. The windows are hooded. The main
door and window above have narrow sidelights. Now housing apartments, this Italianate
building doubtless had a form of lantern atop the roof and was clapboard sided.
54.This pleasant late l9th-century residence, like its next-door neighbor at 107 Maple
Avenue, was designed to take full advantage of the lot's width at a time when traffic was
beginning to increase. The one-storey front porch runs parallel to the road and is set
back, protectively, from the gabled bay-window wing of the house. The occupants thus
enjoyed a good view, both indoors and outdoors, of the passerby. The asymmetrical plan
also allowed for a maximum amount of decoration on the street front.
55.Built for judge James Pearce, son of United States Senator Pearce (see #3) in the
mid-1880's with the help of the capable Chestertown contractor H. M. Stuart, this house is
one of the most striking in Town. Educated at Princeton, Pearce and his wife had
undoubtedly seen some of the more extreme designs around the New York-Philadelphia area in
the Queen Anne style. There is here an extreme picturesqueness of effect in the L-shaped
plan (just the opposite of #53). The roof is irregular and holds dormers of different
shapes; the walls move in and out, supporting open porches and closed, shallow projecting
bay windows. Above all, there is a dramatic variety of colors and textures: brick, timber,
clapboard, wood shingle, stone, stucco, slate and terra cotta. The house is a
tour-de-force (costing $8,000!) which one could not miss on reaching Town from the south.
After leaving the Pearce family, the house served for a time as the Emmanuel Church
rectory. In recent years it has been carefully restored.
56.In 1805 a corporation built a wooden bridge across the Chester River at the foot of
Maple Avenue (then Fish Street). This development added great importance to this
comfortable three-bay brick house, which had been first constructed in the mid-18th
century. In its present form, one can see additions to the left and rear; and although a
19th-century porch that once surrounded the entire ground storey has disappeared, the
lowered, bracketed roof remains, as does the later main doorway. There once stood at the
edge of this important property the small toll house which collected tolls until the
bridge was made free in 1890 by the two counties.
57.Dating from around World War 1, this substantial house stresses the virtues
of solidity, dignity and restraint. Made of hard, dark brick with thin mortar and slate
roofing, the essential lines are severe, while retaining such late 19thcentury amenities
as a solidly built, full-width, large front porch, a two-storey bay window, and the formal
porte-cochere (at left rear).
interesting thing about this early brick residence is that it was for generations the only
dwelling on the town side of this Water Street block. Much of the adjacent land between
Maple Avenue and High Street had been reserved by the waterfront houses for gardens and
auxiliary uses. The house was probably built for the Frisby family around 1766 with a
simple three-part facade. The front wall is in all-header bond while the ends are in
common bond. Only the south wall had windows on two floors; the north wall windows and the
porch are later changes.
59.Built in the third quarter of the 18th century, perhaps for Simon Wickes, this house
resembles #58 in most respects. It likewise has an all-header bond brick front, but the
water table jogs above the basement windows and the north wall is in a fine Flemish bond
with glazed headers. The restoration of the building includes a small porch with benches,
such as are known to have existed in 18th century Chestertown.
60.This waterfront double residence is actually a late 19th century building to which
additions have been made. It harmonizes with other residences in this block because of the
Colonial-Revival entrance porches and the simulated stone architraves above the facade
windows. The scroll brackets at the ends of the roof cornice are clearly from the period
of first construction, however.
61.Known as the Watkins house because Esau Watkins received the land as a wedding gift
in 1739 from his Ringgold in-laws, this may be the oldest house surviving on Water Street.
it is hip-roofed with a coved cornice and is oriented perpendicularly to the street. The
walls are chiefly of Flemish bond with glazed headers but a simpler section was added to
the river front. Much of the detailing is restored.
62.Now known as River House, this National Register landmark was first owned by Thomas Smythe, merchant and shipbuilder, and then Peregrine Letherbury, attorney, during the 1780's. Law professor Peregrine Letherbury was first secretary and later President of the Washington College Board of Visitors and Governors. Letherbury is thought to have completed this very elegant mansion, perhaps the finest of the immediate post-Revolutionary period in Chestertown. Tremendous attention was paid to the high
three-storey facade, which rises above a tall basement. The Flemish bond street wall is framed by slender brick pilasters at the sides, a cut stone water table, and an extremely fine cornice under the low pitched roof. The two main floors are separated by a simple stone belt course and their windows topped with rusticated stone flat arches. The moldings of the cornice are especially refined (egg and dart, dentil, etc.) and serve to tie in the pilaster capitals. The superimposed porches of the river
front and the entrance doorway are the work of Orin Bullock, nationally known restoration architect. The building is currently privately owned and paneling from a second floor parlor is now in the Winterthur Museum.
63.The Richard Hynson house of ca. 1870 originally consisted of a three-storey main
block, two bays deep. The style is in the familiar, by now quite conservative, Italianate,
as can be seen from the hooded first- and second-storey windows, the tripartite treatment
of the main door and the window directly above, as well as the low-pitched, heavy
bracketed roof. Mr. Hynson had a lower rear wing already by 1877, if not before, and this
was further added to by 1885. Today the structure is greatly enlarged to form an apartment
64.Perhaps the most radically transformed early house in Town, the Thomas Anderson
residence of ca. 1796 seems to have been five bays and 21/2 storeys at first and then
modified to suit the Italianate style at mid-century when the third floor, bracketed
cornices, hooded windows and front porch were added. A service wing was in place at the
north end by the later century, certainly, and a marvelous two-storey oriel window of the
Queen Anne type was put on at the south end. Today, its lengthy and irregular facade is
one of the most interesting in this impressive section of the waterfront
65.Widehall is in many respects the Town's most satisfying mansion. Built by Thomas
Smythe, merchant and shipbuilder and perhaps the wealthiest man in Kent County, in this
pivotal location ca. 1770, the house is commodious and quietly formal. The facade entrance
portal is not placed within an impressive central projecting "pavilion" with a
wide pediment along the roof line, as in most mansions of this era (Hammond-Harwood house
in Annapolis or Mount Pleasant in Philadelphia) but its five-bay facade remains flat, as
in the Corbit-Sharp house in Odessa, Delaware. The quality of the building depends on its
fine proportions and well executed details, such as the high stone foundation, the beauty
of its half-columned Doric portal, and the fine frames around the 12 over 12 windows,
which are capped by keystoned flat arches.The house takes its name from the large space allotted for the hall and staircase on
the street side of the house (reminiscent of Mount Pleasant). The dormered hip roof was
restored shortly after 1905 when Mr. and Mrs. W. W. Hubbard acquired the much-altered
house. The tall Ionic porch on the river front is also of this later era, but to Mrs.
Hubbard belongs the credit of being the first leader of historic restoration in
Chestertown. One of the appreciative early residents of this gracious home was United
States Senator Ezekiel Chambers, later judge and President of Washington College's Board
of Visitors and Governors.
OTHER STRUCTURES OF INTEREST
First Methodist Church
The First Methodist Church on High Street, corner of Mill, today appears as a handsome
Colonial church in a beautifully maintained state. In actual fact, the structure was built
in 1877 at a cost of about $20,000 in a symmetrical Gothic style, complete with
medieval-looking steeple. During the 1920's this prosperous congregation wanted to enlarge
the church complex and do over the main building in the increasingly fashionable Colonial
Revival style. A new Ionic portico was erected in front of the old tower, which was itself
done over in the Georgian idiom. Most of the original church has been masked out by
alterations, but a careful study of the lower side walls reveals the vestiges of the old
Gothic buttressed wall. First Methodist Church presents the case of a well-intentioned
improvement of a building. Handsome though the result may be, a part of the past has been
Palmer "Rock of Ages" (532 High Street)
This modest 1 ½ -storey dwelling at the upper end of High Street has long been thought
to be one of the oldest in Town (mid-18th century). It is the only early structure of
solid stone, certainly, and appears in a very old photograph with a one-room addition at
the northwest end. The present front porch is less than a century old.
Colin Stam House (114 Washington Avenue)
The house of entrepreneur Colin F. Stam at the foot of Washington Avenue marks an
important transition in the life of the Town, namely the development of an impressive row
of residences on the main road leading out to Washington College. Stam's house was built
in 1877 for about $4,000 (in the main section) by local builder H. M. Stuart. It is an
eclectic design which mixes Gothic elements with some Second Empire characteristics that
were to be used in more florid fashion in Stam's Hall of 1886. The masonry work in the
chimneys is especially well done.
125, 127, and 129 Washington Avenue
These three comfortable homes illustrate the rapid growth of Washington Avenue in the
late 19th century when the College began to open its lands on a 99 year lease basis. All
three wooden buildings feature large gables facing the street with the rest of the house
massed alongside, two with stout towers. Extensive verandahs with intricate detailing
still surround these buildings, adding to the feeling of spaciousness. Their style may be
referred to nowadays as Queen Anne, a rather loose term. In their day they must have
seemed to their occupants a wonderful escape to the outlying countryside. No. 125 has some
especially fanciful decorative trim surviving. Color schemes for such houses were never
all white, however.
Bungalow at 311 Washington Avenue
This delightful dwelling marked the first arrival in Town of a Sears & Roebuck
prefabricated bungalow. This class of house had great vogue in California, and the present
example, which features a low, wide, tiled roof, is in the "Craftsman" style. It
arrived in Town by rail in 1926.
WASHINGTON COLLEGE HILL BUILDINGS
Between 1845 and 1854, three rectangular-shaped buildings were erected on the brow of a
hill, facing town, to comprise the new Washington College campus. They were erected
precisely over the site of the College's first building which was destroyed by fire in
1827. The earlier building, constructed under the leadership of Dr. William Smith and with
the support of General George Washington, had been begun in 1784. Excavations at the site
in 1981 proved that the building had measured 160 feet across the main front, making it
one of the largest 18th century Georgian buildings in Maryland and one of the
largest College edifices in the new nation.The new center building, Middle Hall, was used for classrooms and dormitory. There are
vestiges of the Greek Revival in its broad banded exterior cornice, but the porch details
and the roof lantern (reconstructed) are in the more up-to date Italianate mode. East and
West Halls, built slightly later, are simpler and have more vertical proportions. All
three buildings are of hard, dark brick with thin mortar joints and have low metal roofs,
common in the mid-century (see #36). Washington College is Maryland's oldest institution
of higher learning and the three buildings are on the National Register of Historic
THE CHESTERTOWN HISTORIC DISTRICT COMMISSION
In 1732, a generation after the founding of Chestertown at its present site, the
Maryland Assembly passed a law, requiring that all sheep, geese and swine be kept penned
up in town because of the nuisance and danger they caused. In 1963, the Maryland
legislature passed another protective law for the common good - one already approved in
several other American states and in many European countries - a piece of legislation
allowing local governments in the State to watch over their architectural heritage.The Town of Chestertown was quick to recognize the value of this enabling legislation
(Maryland Annotated Code, Art. 66B) by adopting an ordinance in the very next year, giving
full powers to a locally appointed seven-member commission. This group now meets in formal
public sessions the first Wednesday of every month to consider applications for work to be
done within the "Historic District," as defined by the ordinance. The work in
question is exterior work that will be visible from the "public way."The following are examples of the sort which require a permit: signs; auxiliary
structures, such as sheds and fences; additions to a main structure, such as porches,
wings, dormers, chimneys, shutters, railings, or the removal thereof; replacement or
recovering of the sides or roofing of a building, whether in part or entirety; painting
masonry surfaces; the construction of entirely new buildings or the demolition of existing
buildings. The Town Office is in a position to advise the public further as to what work
falls within the requirements of the law.The seven Commissioners are civic volunteers who give of their time and experience and
who are more than happy to assist their fellow citizens in making appropriate decisions
which will both meet owners' needs and at the same time fit the criterion of architectural
propriety. Purely conceptual approvals cannot be given, however.The fairness and correctness of the Chestertown Commission's proceedings have been
substantiated in some important higher court rulings (which have attracted national
attention) and, more recently, in the National Park Service recognition of Chestertown as
a Certified Local Government (the fourth in Maryland to be so approved). Chestertown has a
National Landmark District, and that district was listed with the National Register of
Historic Places in 1968. The National Register District was further expanded in 1984,
Additionally, the Chestertown government now has the authority to nominate individual
buildings to the National Register.
This guide was produced by the Mayor and Council of Chestertown, using matching
grant funds received from the National Park Service, United States Department of
the Interior. These Federal funds were administered by the Maryland Historical
Trust through the Certified Local Government Program.
The text of this guide was written by Robert J. H. Janson-La Paime. Assisting in
research was Kathleen B. White. The Project Coordinator was William S. Ingersoll.