A tour of notable homes, inns and public buildings decorated for the holidays

Venerable Chestertown, replete with a glorious past, filled with historical significance welcomes visitors to its annual Christmas tour of homes and public buildings.  Progress has not eradicated the town’s treasured traditions and quaint customs.  Still holding out with admirable obstinacy are old landmarks in the form of clapboard, stone and time-bleached brick homes and public buildings that have weathered three centuries.  A few blocks north of Chestertown’s historic district is Washington College, a National Registered Historic Landmark founded in 1782, which, with the consent of George Washington, bears his name.
            Christmas in the eighteenth century was celebrated as a season, not just on one day.  The festivities extended from Christmas Eve through the Twelfth Night (January 6th), a time when Chestertown homes and nearby manor houses were the scenes of gaiety, visiting, hearty eating and drinking and dancing.
            Although some of Chestertown’s festivities have no historical reference to the 18th century, it is believed that they add to the enjoyment of the season.  Wreaths of evergreens hanging at the windows, fragrant garlands of juniper, cedar, balsam and scotch pine wrapped around banisters, the decorated town square in Chestertown with the cast iron fountain and old lamps – the holidays in Chestertown are a glorious treat of sights, sounds and scents.
            We hope you enjoy the tour and most of all would like to thank you for your generous donation. 

1. Widehall
101 North Water Street, Chestertown

Widehall was built in 1770 by Thomas Smyth, a merchant and shipbuilder. He was thought to be the wealthiest citizen in Kent County at that time. The mansion is a wonderful example of Georgian architecture with notable features such as the half-columned Doric portal, five bay flat façade, and its all header bond brickwork and framing work around the 12 over 12 windows. The house’s name comes from the large space allotted for the hall and staircase on the street side (widehall).
Over the years, Widehall has had many owners and several renovations. During the past several years, the house and gardens had undergone a major restoration resulting, once again, in making Widehall one of Kent County’s impressive landmarks.
Owner: Mr. Roy Kirby

2. Custom House
101 South Water Street, Chestertown

This house was built circa 1745 by Samuel Massey and sold in 1749 to Thomas Ringgold. It is assumed that the building was the residence of the customs collector. The beautiful façade of this building is made of Flemish bond brick work with glazed headers. A doorway to an adjoining stone building that no longer stands, was uncovered during recent restorations. Under the terrace were three arched vaults, one still open, that was probably used for storing imports until the duty was paid.
Owner: Washington College

3. Hynson-Ringgold House
106 South Water Street, Chestertown

The house was named for Nathaniel Hynson, Jr. and Thomas Ringgold, Jr. Ringgold purchased the house from Dr. William Murray, who had constructed the front portion in the early 1740’s. Ringgold built the remainder of the structure in the late 1760’s, tripling the original size. He was responsible for the magnificent mahogany antler stair as well as the remodeled northeast side of the house.
The house is listed in the National Register of Historic Places and has been the home of the presidents of Washington College since the late

1940’s. The Washington College Women’s League will again serve as docents.

Residents: Dr. and Mrs. Baird and Sarah Tipson
*Note: This site will close at 4:00 p.m.

4. Fort Belvedere
201 South Water Street, Chestertown

Built in 1857 by James Taylor, this frame “four square” with its lantern or belvedere offering commanding views of the Chester River has been dubbed Fort Belvedere by the owner and combines aspects of both Greek Revival and Italianate styles. The double parlor, with its graceful archways, boasts matching mantels and operational “jib” doors. The kitchen with steep formica cabinets reaching to the ceiling, has a floor of burgundy-colored rubber. Of note, in the parlor and dining rooms are large collections of mercury glass and majolica.
Owner: Mr. William Creager

5. Levi Rogers House
202 South Water Street, Chestertown

The Levi Rogers House (Circa 1740) is one of the oldest houses in Chestertown. In the 1840’s the house was owned by Levi Rogers, who ran an oyster house at this address or at a building nearby. Legend says that Ella Fitzgerald once sang here. The house was on the Chestertown Tea Time Tour in October 2005 immediately after its completed restoration and addition. The project took two years. The house now has approximately 2800 sqft of living space.
The restoration and addition were designed by Virginia architect Peter Wren, direct descendant of Sir Christopher Wren, famous 17th century English architect (St. Paul’s Cathedral, London). The house is a blend of 21st century technology, amenities, and features and Pre-revolutionary history.
Owners: Zane and Sally Markowitz

6. Bolton House
137 North Queen Street, Chestertown

The oldest section of the Bolton House, 21' by 18' one-and-a-half story structure, was built c. 1756. The outside of which had feather edge shiplap siding painted the typical red of the period, a small portion of this can be viewed through an opening in the expanded entrance hall. Additions were made to the house in the 1770s and the 1780s, as well as the kitchen area, which dates to the late 1800s. The owners have a collection of Santa Clauses, which are displayed through out the down stairs. Some of these date back to the early 1900s and several are from the owner’s childhood. There is also a collection of 13 Lenox Christmas plates, one for each of the original colonies, displayed in the living room.
Owners: Mackey and Fred Dutton.

7. Metcalfe House
213 North Water Street, Chestertown

Built in 1910, this frame, three story home with a welcoming front porch, has elements of the Edwardian style: a large pocket door opening from foyer to parlor and a second one into the dining room. The pocket door off the foyer has been updated to incorporate beveled glass panels, opening up the parlor while maintaining its sense of intimacy. The home’s chimney stack, removed in an earlier modernization, has been restored by the Hegland family who also added a handsome imported marble fireplace surround in the parlor. The heart of this waterside home is its impressively appointed kitchen. Renovated in 2002, the kitchen now overlooks a dining and sitting area in the large River room and provides the cook with an unobstructed view of the Chester River and the home owners’ dock and garden. The reconfigured space once housed the original kitchen, a walk-in pantry and a small laundry room. Throughout the home, the owners display pieces from their collection of contemporary American craft.
Owners: David and Patti Hegland

8. Geddes-Piper House
101 Church Alley, Chestertown

Built in 1784 by James Piper in the Federal period townhouse style, this three-and-a-half story brick structure is the headquarters of the Historical Society of Kent County. Lot #26 of the 1730 re-survey of Chestertown was at one time owned by William Geddes, custom collector of the Royal Port at Chestertown.
The Geddes-Piper House now houses a highly prized collection of Chinese export porcelain teapots, portraits of early Kent County citizens and 18th century antiques. There is a delightful childhood of the 1880s room on the 2nd floor.
Owner: The Historical Society of Kent County

9. Emmanuel Church
101 North Cross Street, Chestertown

This church, built in 1767, is the third one on this site. Originally, the main entrance was in the south wall where there is now a Tiffany stained-glass window which was produced at the Louis Comfort Tiffany Studio in New York. The building was reoriented to east-west in 1880, where the asp and narthex were added. Notable is the oldest artifact, a marble memorial tablet, set in the north wall of the preceding church in 1757.
In 2002, the kitchen was completely refurbished. In addition, improvements were made to the Parish Hall and upper areas, now utilized by the choir and Sunday School, as well as the beautiful new memorial garden.
Steward: The Parishioners

10. Parker House
108 Spring Avenue, Chestertown

The Parker House was built in 1876 for the grandfather of present Chestertown residents John, Thomas and Walker Eliason and their sister Mary Margaret Forney. Mr. Eliason had built for himself and his family what had been termed a “farm house”. He did not like the frills associated with Victorian style, so his house is simply BIG, with large, square and high rooms. The barn in the back housed cows.
All of the fireplaces in the house are made of slate, etched and worked to simulate the look of marble. The yellow pine floors are original with the house.
Modifications to the house were made in the 1970s by then owners Walker and Betty Ann Eliason such as adding the current kitchen and porch. The current back room was the original summer kitchen and the dining room was originally the kitchen.
Several other modifications were made by the Parkers to convert the house to a bed and breakfast.
Parking is in the rear, accessible from Mill Street, and guests may enter through the back and view the grape arbors and garden.
Owner: Mr. John Parker

11. Davis-Johnstone House
105 South Mill Street, Chestertown

This charming, small-scale clapboard house was built by Charles Davis around 1854 on part of Lot No. 84 in the original plat of Chestertown. The double house was built on a brick foundation with four bays, the inner two of which have doors with transoms. Three dormer windows complete the front façade. The interior spaces were originally divided evenly with one front room each, with an enclosed stairway to a small chamber above.
From 1916 to 1959 the house was a tenement and gradually deteriorated. In 1959 a new owner began restoration and rehabilitation making it a single family dwelling. In the mid-1970’s the house was abandoned and left unoccupied until it was purchased in 2003.
This was the second time in its history the house was to be saved from the elements and termite infestation. The current owners have made every effort possible to save and retain all architectural features during its renewal and restoration. The house has been completely modernized throughout, new additions have been made, new patios, walkways and landscaping.
It is open for the first time on this tour.
Owners: Mr. and Mrs. Eugene H. Johnstone

12. Cliff’s School House
Quaker Neck Road, Cliff City

Cliff’s School is the last remaining one-room school house in Kent County still in its original configuration. It served grades one through seven. It was constructed in 1878 and was in use until 1939. The lessons on the blackboards, the books, stove and desks are all in place as they were on the closing day. On the old double desks are many vintage text books including McGuffey’s Eclectic Primer (1881). There are original slates and many other fascinating artifacts of the period. Even the Christmas tree is decorated with the trimmings of the time.
The schoolhouse is maintained by the Port of Chester Questers and the Retired Teachers of Kent County.
Please note that Cliff’s School House is approximately 9 miles out of Chestertown. Refreshments will be served to visitors.