Beginning with a Governor’s proclamation in 1668, the idea of establishing a port of entry at this spot on the Chester River had been kicked around for years. A court house was built here in 1697 and when that colonial port was officially decreed in 1706, it assured the founding of a town. 

A broad main street (called High today, platted at 90 feet wide) led from the river to the chief public space, situated at the intersection of a crossing street (called Cross) where the places of public business and other amenities are located. The simplicity of this scheme, similar to what William Penn was doing in 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.

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. Its location squarely on the most heavily traveled North-South road in Colonial America forged significant new ties with Philadelphia in the period just preceding the Revolution. George Washington is known to have made at least eight visits tot he town, including dining on May 23, 1791. At Worrell’s Tavern that operated at Queen and Cannon streets. Washington donated money and lent his name to the college, which opened as Maryland’s first and the first in the new nation after the Revolution, in 1782. He served on the board of directors and was given an honorary degree of doctor of laws in 1789. The bronze figure of Washington on campus was executed by Lee Oskar Lawrie.

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. Fruit growing and the coming of the railroad to Chestertown in 1872 partially account for this boomlet, 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.

Our walking tour will start on the banks of the banks of the Chester River; the commercial wharves are long gone but the buildings and streets their wealth spawned remain...

Chestertown Tea Party
foot of High Street at Chester River

On May 23, 1774, “a group of Chestertown citizens undisguised and in broad daylight” boarded the brigantine Geddes, owned by Custom Collector William Geddes, and threw its cargo of tea into the Chester River. The town then became a faithful supplier of provisions to the town f Boston, then suffering under the Boston Port Act. Chestertown remembers its REvolutionary heritage during the Chestertown Tea Party Festival held during the Memorial Day weekend.

The Custom House
101 S Water Street, southeast corner of High Street

Chestertown was an official Port of Entry, one of just six in the Maryland colony created by the General Assembly, under pressure from the Crown in 1706. That original Custom House is no longer standing. This Custom House was constructed by Chestertown merchant Samuel Massey in 1745. Massey embellished his Flemish bond brickwork with glazed headers. In 1749, Massey sold the property to Thomas Ringgold IV, a member of the House of Burgesses, attorney, land speculator, slave trader and merchant who imported goods from Europe and the West Indies. In 1771, Ringgold built an addition onto the rear of the building, which was used as the residence, while the front was converted to a dry good store. Prior to the Revolution, Ringgold rented out space to the District Customs Collector, which was probably located in an adjoining building that was torn down and replaced the early 1900s. It was from this association that the Custom House got its name. When Chestertown declined in economic importance in the late nineteenth century, the Custom House was converted into apartments. Fortunately, many of the original details of the house were restored by local preservationist Wilbur Ross Hubbard, using funds provided by the Maryland Historical Trust. When Hubbard died in 1993, he bequeathed to Washington College the landmark property. 


Captain James Frisby Taylor
201 S Water Street 

Captain James Frisby Taylor purchased this riverfront property in 1857. He built a wharf and leased it to the Chester River Steamboat Company, of which he was an agent. For his home, Taylor drew on his extensive travels around the Chesapeake and in Baltimore to select the latest style - the Italianate villa. Despite passing through the hands of nearly a dozen owners since, the house retains its detailed lantern on a low-pitched roof and displays a rich series of ornamental brackets under the eaves of both the main roof and porches. Fine too are the jigsawn porch balustrades and the general proportioning of the building. Its symmetry and open, airy feel are hallmarks of the Italianate style.


Hynson-Ringgold House
106 S Water Street 

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 contrast contrasts vividly with the Taylor House on the opposite corner. William Murray purchased the lot in 1743 from Nathaniel Hynson and erected the front section with its impressive facade. Thomas Ringgold, a 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. 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). Also attached to the property is the large walled garden a spacious open lot in front which affords an unbroken vista of the Chester River. 


The Wickes House
102 High Street

This imposing Georgian style house is most associated with the Wickes family, one of Chestertown’s most prominent families, who owned it from 1832 to 1943. But construction was initiated by the Wallis family, and the clean four-square Flemish brick construction fits the generation of building just prior to the American Revolution. It has five bays, a gabled roof with dormers, and 15 fireplaces - all original to the main house. Most mantels, moldings and floors are original.   

William Barroll House
108-110 High Street

This was originally a five-bay single residence, possibly built as early as 1743 by owner William Dougherty. William Barroll, a prominent local attorney, bought the Georgian home in 1797 and expanded it 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.

123-125 High Street

This is an extremely handsome Victorian brick double-dwelling, especially notable for an ingenious repetition of an arch motif on the facade, beginning in the door panels, moldings and transom and carried out in the windows, arches and dormers. The building is unusually well-constructed and though broken up into a number of apartments it remains in excellent repair. It was designed as a double dwelling from the start.

Cahall Store
127 High Street, southeast corner of Queen Street 

Thomas Hynson bought this corner of High and Queen streets between 1848 and 1855 for a total outlay of $560. He built the double house next door and this vernacular Italianate building as store. 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-story windows can be explained by the fact that the old retail district of the Town began at about this point on High Street. After shopkeeper Cahall passed away in 1933 he willed the property to the Methodist Church and the building did duty as the Chestertown Library.  

Buck-Bacchus Store
116 High Street, northeast corner of Queen Street  

On this corner stands one of the earliest brick houses remaining in Chestertown, dating to 1735. John Buck, a merchant from Bideford, Devonshire, England, bought the lot and set about building two tenements. Buck, whose family exported pottery and woolen cloth to the American colonies as early as the 1600s, likely never lived here but used the building as a storehouse. Buck was known to have plantations in Maryland and Virginia and a sawmill in Maine. By the time the house was sold in 1854 to William Bachus, the lot had been reduced to a fraction of its 1735 bounds. Bacchus and his family not only kept up the store but made this their home as well. The building stayed in the Bacchus family until 1922. Finally in 1975 the building was purchased by Preservation, Inc., a local group, and the Maryland Historical Trust, and restored. 

201-203 High Street

Long neglected, this prize example of a retail establishment with a low-pitched hip roof, 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.

Imperial Hotel
208 High Street 

The Imperial Hotel with double tiered verandah was erected in 1903 by W. W. Hubbard for use as office and store as well as a place of lodging. 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.

Prince Theatre
210 High Street 

The first “movies” involved outdoor summer shows on the parking lot of the Bates Russell Motor Company building in the early 1900’s. In 1909 Russell bought Stam’s Hall and on Saturday, September 4, on the second floor, the movie house opened for a 7:30 p.m. show with an admission charge of five cents. In 1928 Russell bought the butcher store next door (here) and built this movie house, that opened in 1928 as the New Lyceum. In 1957 Charles E. Prince purchased the business. “Pete” Prince, who started in the movies in 1922 at the age of nine selling popcorn at a Nashville movie house, had never lost his love for the movies. He preserved the old theater until his death in 1988. Then his wife Kit kept it open until 1991. Now maintained by the Prince Theatre Foundation, the yellow brick in the front of this building is unusual for the town, though fashionable architects began to use this color by the 1890s elsewhere. 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-story window arches. Although the ground-story bricks have been painted, much of the roof and marquee treatment appears to be original.

Stam’s Hall
220 High Street 

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 $1,000 to pay for a bell in the tower, which still tolls the hours. The Second Empire-style 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. 

Chestertown Bank of Maryland
211 High Street 

This impressive Beaux Arts bank was built in 1929, but it came at the expense of the tall five-bay brick Tilghman House that had stood here since the 1790s. 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 Neoclassicists. 

White Swan Tavern
231 High Street

This Colonial-era tavern was one of many in Kent County, of which few survive. The White Swan, as local legend calls it, dates to the mid-1700s. It is a two-and-a-half story, dormered brick building with colorful glazed headers in the Flemish bond facade on High Street. Another legend that passes through some history books is that George Washington bunked here in October 1774. During the 1800s the inn was known as the American Hotel. A major restoration program in the late 1970s restored the old tavern building 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. In 1981 the tavern reopened as a bed & breakfast.


1908 Volunteer Fire Company
113 S. Cross Street 

Constructed between 1908 and 1909, this was the Town’s first sizable volunteer firehouse. By the 1890s 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 two-story, flat-roofed building is noted for its facade of concrete blocks and cast concrete lintels, sills, and name plaque. The fire wagon and passage doors date to the original construction. 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. 

Chestertown Railroad Station
Railroad and Cross streets 

The railroad line on which this station is located was laid in 1869-72 for the Kent County Railroad. W.S. Culp, a local contractor built this station for the Pennsylvania Railroad, the owner of the line by that time, in a popular timber and stucco Queen Anne style in 1902-03. Then he became the first station master and telegraph operator. The railroad operated until 1968 when the Pennsylvania Railroad shut down freight service to Chestertown. The charming station was later moved 44 feet from the foot of Cross Street to allow for improvement of the thoroughfare. It is the only railroad station extant in Kent County and the only structure remaining associated in any way with transportation.


Methodist Protestant Church
southwest corner of Cannon Street and Cross Street

Originally built as a church in 1859, this edifice has spent most of its life in secular uses, including a stint as the Kent News Building. 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.   

Janes United Methodist Church
120 S. Cross Street 

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 virtually unchanged.

108 S. Cross Street 

This nicely proportioned three-story 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 story fit the “Prairie,” while the subdivided arched window of the middle story is in the Renaissance mode. The short tile roof over the entrance is a later addition.


Bordley Corner
301 High Street

Thomas S. Bordley, a haberdasher claimed this prime retail corner in Chestertown in 1883. His shop burned in the fire of 1910 and this building was put up the following year. 

Chestertown Pharmacy
329 High Street

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.

Lusby House
359 High Street 

This frame house designed in the Italianate style replaced a one-and-one-half story structure that was the rectory for the Emmanuel Church around 1860. 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. Its list of owners include Harrison Vickers, son of Senator George Vickers who lived in a large Italianate house of his own on the opposite corner where the school was built in 1904, and Josiah Lusby, who purchased the house in 1885. It remained in the family until 1964. 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.


Sterling Castle
103 S. Mill Street 

Ebenezer Blackiston was this first owner of this property, Lot No. 84, when he purchased it in 1730 from Simon Wilmer. Robert Sterling, a Lieutenant in the British Army, purchased part of the lot in 1756 and built a one-and-one-half story house three bays long and one deep. In 1759, Sterling was forced to sell the house and all its contents for 100 pounds. The creditor, Richard Porter, thought so little of the little abode that he referred to it derisively as “Sterling Castle.” It kept the name, even as it picked up additions through the decades. 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 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.


James Anderson House
400 Cannon Street  

It is likely that Elias Ringgold built on this lot after he purchased the land in 1733. James Anderson bought the property four years later when Ringgold died and replaced the frame house with this large Georgian brick home, one of only two in Town to feature an early lean-to addition, known locally as a “catslide roof.” It remained in the family until 1866.


Christ Methodist Church
401 High Street 

Despite the popular appeal of the Gothic Revival style in America from the 1830s onwards, very few examples can be found today in the Chestertown. 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. This is one of the most richly ornamented buildings ever constructed in Town. Gothic arches, stained glass and buttresses are found all around. 


Hubbard House
402 High Street 

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 house.


Public School Building
400 High Street 

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-story Italianate residence that faced Mill Street. Now it is used as Kent County offices.

First United Methodist Church
105 N Mill Street, northeast corner of High Street  

This handsome Gothic Revival church was built in 1875; the congregation organized in 1780. The tall spire and side-and axis pilasters and modillions remain from the original building.


Methodist Meeting House
southeast corner of Spring Avenue and Park Row 

This was the first permanent Methodist church in town, 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, laid in Flemish bond, 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). The first American Methodist Bishop, Francis Asbury, preached here and, according to his letters and journals, found Chestertown “a very wicked place.” 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.

Chestertown Post Office
104 Spring Avenue

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-story 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. 


Hackett House
314 Park Row, northeast corner of Spring Avenue 

Between 1765 and 1770 this lot, No. 41, was owned jointly by Benjamin Morgan and William Sluby, Jr., merchants trading under the name of Morgan & Sluby. Charles Hackett bought the northwest half here in 1806 for $500 - prime selling territory opposite the old Market Square. He built the five-bay, 2 1/2-story, central doorway clapboard building, the oldest still standing along Park Row and one of the few remaining in Town. Two lots to the rear off Spring Avenue, there stands an original, early, small brick smoke-house, belonging to another property.

Rockwell House
300 Park Row 

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. 

Fountain Park
bounded by High Street, Spring Avenue, Park Row and Cross Street

Fountain Park was created by the Ladies Improvement Society, forerunner of the Chestertown Garden Club. The current fountain, crowned by Hebe, goddess of Youth and Beauty, and cupbearer to the Gods - was erected in 1899. Historically, this was the town’s market place. 


Kent County Courthouse
103 Cross Street 

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.


Emmanuel Church
northeast corner of Cross Street and Park Row

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-story, 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 1880s 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.

Masonic Temple
100 Park Row 

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 story, 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 story. A one-story clapboard addition was put on, perhaps as early as 1877, to accommodate the demand for this central location. 


Lawyer’s Row
113-115-117 Court Street

It is common in small rural Maryland towns to find Lawyers’ Rows in the county seat, near the Court House. These three buildings, all built sometime after 1850, are examples of those earliest buildings extant for that purpose in Chestertown. At No. 113 the 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. Perhaps the most satisfying example of its type, at No. 117 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.

Original Library
119 Court Street

This one-story framestructure with simple brackets under a plain box cornice served at the original library building in Town.


Church Alley Store
106 Church Alley  

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 was built on the site of the “old Sturgis house” after it apparently burned down in the mid-1800s. It served as a store into the 1950s and has been neatly restored at ground level to its former appearance. A “catslide” roof can be seen around to the rear.

Geddes-Piper House
101 Church Alley

This impressive 3 1/2-story 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 1780s when full three-story elevations were common in Atlantic coastal towns and the present form of the house with its rear wing resembles the finest Federal homes 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 No. 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 pedimented doorway. 


Nicholson House
111 N. Queen Street

Narrow Queen Street features many late 18th and early 19th century tradesmen’s homes as well as more substantial merchants' homes, of which this is an example. Captain John Nicholson built this Federal-style town house in 1788. Nicholson was the youngest of three brothers, all of whom were prominent in the Navy during the Revolutionary War. John served as Commander of the Continental sloop Hornet; James was head of the Maryland Navy and then head of the Continental Navy; Samuel’s career culminated in the 1790s when he commanded and supervised the construction of the United States Navy’s flagship, the U.S.S. Constitution


Burchinal House
113 Maple Avenue

The William Burchinal House, built for one of the town’s prominent merchant families, is one of the principal essentially Greek Revival style frame dwellings in Chestertown, its original aspect marred only by asbestos shingles added in the 1950s.

107 Maple Avenue

Stick Style decorations in the gables and dormers and on the roof enliven this L-shaped frame house. The late 1800s residence was designed to take full advantage of the lot’s width at a time when traffic was beginning to increase on this primary thoroughfare through town. The one-story front porch runs parallel to the road and is set back, protectively, from the wing of the house. The occupants thus enjoyed a good view, both indoors and outdoors, of the passerby.

Pearce House
103 Maple Avenue

Built for judge James Pearce, son of United States Senator Pearce in the mid-1880s 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. 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.  

Chester House
201 N Water Street, southeast corner of Maple Avenue

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 (a cat-slide roof slopes towards the Chester River); and although a 19th-century porch that once surrounded the entire ground story 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.


112 N Water Street

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, the essential lines are severe, while retaining such late 19th century amenities as a solidly built, full-width, large front porch, a two-story bay window, and the formal porte-cochere (at left rear).

Frisby House
110 N Water Street  

For generations this early brick residence was 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. 

Perkins House
115 N Water Street

Built in the third quarter of the 18th century, perhaps for Simon Wickes, this house resembles the Frisby House 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.      

111-113 N Water Street 

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. 

Watkins-Bryan House
109 N Water Street 

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.

River House
107 N Water Street  

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-story 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 outside Wilmington, Delaware.

Anderson House
103 N Water Street

Perhaps the most radically transformed early house in Town, the Thomas Anderson residence of the 1790s seems to have been five bays and 2 1/2 stories 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 and a marvelous two-story 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 streetscape.

101 N Water Street

Widehall is in many respects Chestertown’s signature mansion. Thomas Smythe, merchant and shipbuilder and perhaps the wealthiest man in Kent County, placed his residence in this pivotal location around 1770. Smythe served as the head of Maryland’s Revolutionary Provisional Government from 1774 until the State’s first Constitution was adopted in 1776. The mansion is a picture of symmetry and proportion that stands with the best of Georgian architecture in the Middle Atlantic region. It is notable for its half-columned Doric portal and a five-bay facade that remains flat to reveal the beauty of its all-header bond brickwork. Fine frames surround the 12-over-12 windows that are capped by keystone flat arches. The house takes its name from the large space allotted for the hall and staircase on the street side of the house.