Cambridge, the county seat of Dorchester County and the fourth largest town on the Eastern Shore, is one of Maryland’s oldest, settled in April of 1684. Located on the Choptank River, the land that was to become Cambridge was part of the Choptank Indian Reservation. In the early 1700s the town prospered from trade in tobacco, seafood, and muskrat.

The town incorporated in 1794 and was an area of growth due to the completion of the Dorchester and Delaware Railroad and a growing oyster and manufacturing industry. By the mid-1800’s the first large manufacturing industry was located on the east side of Cambridge Creek. Large lumber and flour mills supplied timber to the Central Pacific Railroad for building rail cars, in addition to packing thousands of barrels of flour. This lead to the building of large coastal vessels. made from local pine and oak, on Cambridge Creek. Skipjacks, bugeyes, and log canoes were just a few vessels that local builders developed, in order to meet the needs of those who worked and traded on the Chesapeake Bay.

The Choptank is home to some of the finest oyster grounds in the Chesapeake Bay where sailing skipjacks and hand-tongers still dredge for oysters. Oystering became so profitable that laws were passed restricting dredging of oysters in Dorchester waters to only citizens of Dorchester County. The Oyster Navy was armed to guard the oyster beds from poaching by residents of nearby Somerset County, Baltimore City, Philadelphia, and New Jersey. Conflicts resulted in at least one death.

This prosperity led Cambridge to become the home of governors, lawyers, and landowners. Their beautiful homes line High Street, Water Street, Mill Street, and Hambrooks Boulevard. The most famous resident, however, was Sharpshooter Annie Oakley who built her house at 28 Bellevue Avenue, on Hambrooks Bay. The roofline was altered so Oakley could step outside her second-story windows and shoot waterfowl coming in over the bay.

Our walking tour will start on the banks of the Choptank River and walk down the street that James Michener used as a model for his sprawling novel Chesapeake into the heart of the Cambridge historic district that was so designated in 1990...

Long Wharf Park
Water and High Streets at Choptank River

Overlooking the Choptank River, this waterside park and marina has been known in the past as Memorial Park with a marble monument composed of a central shaft topped by a carved eternal flame and flanked by low walls. The base of the shaft carries the carved inscription, “PEACE TO THE MIGHTY DEAD, 1941-1945.” The top edges of the walls carry the raised inscription, “IN GRATEFUL MEMORY OF OUR VETERANS OF WORLD WAR II.” The Nathan, a traditional Chesapeake Bay skipjack built to preserve the nautical heritage of Dorchester County is berthed at Long Wharf Park at the end of High Street. The Nathan offers two-hour sails on the Choptank River when she is in Cambridge.  

Frederick C. Malkus Bridge
Choptank River

Prior to the Governor Emerson C. Harrington Bridge which was built over the Great Choptank River in 1935, ferries were used to cross the river. It originally had a swing span to allow passage of vessels and President Franklin D. Roosevelt was on board his presidential yacht Sequoia, when it became the first vessel to pass through the draw. The President then came ashore and delivered a congratulatory speech at Long Wharf. A memorial to Franklin D. Roosevelt and the faux smoke stack (it was actually an elevator shaft) from his later Presidential yacht, U.S.S. Potomac, is located here. Remains of the Depression-era bridge are used as fishing piers on both the north and south bank of the river. This bridge was replaced by the higher none-span Frederick C. Malkus Bridge in 1987. It is the second longest span bridge in Maryland after the Chesapeake Bay Bridge.   


Williams House
100 High Street 

This house, constructed after 1878 by Thomas Williams, a doctor, was originally located several lots up High Street, on the west side of the road. The frame house features a mansard roof and Jerkin-head gables and dormers.

Ellen Goldsborough House
102 High Street

This house was built for Phillips Lee Goldsborough who was the governor of Maryland between 1912 and 1916. The architect was J. Benjamin Brown, whose fingerprints are all over historic Cambridge. A pediment with molded plaster ornamentation is the only standout decorative feature of the plain exterior. 

Thomas House
103 High Street 

This house was built in 1884 by Captain William J. Thomas, who inherited the land from his father. Several decades earlier the office of Captain Sadrack Mitchell stood on the property. The frame house is designed in the Second Empire style and features a covering mansard roof.

Byrn House
108 High Street

This property was once part of a lot stretching from Commerce Street to the river, known as the “Old Common.” Ownership dates back to 1747 and wound its way to Mrs. Clara W. Byrn in 1887, wife of W. Wilson Byrn, first president of the Dorchester and Delaware Railroad Company. She built this rambling house on the northern half of her lot, influenced by the Shingle Style and originally covered in brown shingles. It has since been converted to apartments.

Muse-Goldsborough House
111 High Street

James Muse, a local doctor, built this Greek Revival brick house in 1849. It was “Victorianized” a decade later by the addition of an elaborate scrollsaw porch with iron finials but retains original features such as long, narrow windows and the interior layout. It was later the birthplace of Phillips Lee Goldsborough, destined to be a governor of Maryland.

Cambridge House
112 High Street

In preparation for his book Chesapeake, James Michener stated that the two blocks of High Street was one of the most beautiful streets in the country. The original section is a small framed cottage built in 1830. It was expanded for a sea captain between 1847 and 1900 to become the Queen Anne style brick mansion it is today.

Granmar House
116 High Street

This was the original home of Reverend Daniel Maynadier, a French Huguenot who was forced from France following the revocation of the Edict of Nantes and sailed to the Chesapeake where he became rector of the Great Choptank Parish from 1765 to 1772. It was rebuilt in 1840 by Henry Page, a lawyer and state senator.

117 High Street

This slice of High Street is dominated by large Queen Anne-style houses. This one is topped by a widow’s walk at the peak of the hip roof. There is a large lip-roofed dormer on the front of the house with a Palladian window.

Goldsborough House
200 High Street

Charles Goldsborough once owned more than 10,000 acres of land in Dorchester County. His son, Robert, studied law in England, became sheriff of Dorchester County in 1761 and was eventually named a delegate to the Continental Congress in Philadelphia in 1776. His son, Charles, built this two and a half story painted brick Federal-style house with a five-bay symmetrical facade as a young lawyer in 1793. He later served as Governor of Maryland in 1818 and 1819. The house features an Ionic-columned entrance portico.

Stewart House
203 High Street

Not much is known about the original house that stood on this property; its current appearance is attributed mostly to Judge James A. Stewart, who bought it in the 1850s. Stewart moved the house, painted red and sitting directly on the pavement with an overhanging portico like a store, back on the lot. He enlarged the building and added the Greek Revival columns. Stewart was born in 1808 and practiced law in Cambridge. He edited the Cambridge Chronicle for two decades until 1843 and dabbled in real estate and shipbuilding over the years. After running unsuccessfully for several political offices he was appointed a judge and won three elections to the United States House of Representatives before the Civil War.

Sullivane House
205 High Street

Dating to before the Revolutionary War, this is considered to be the oldest documented house “built” in Cambridge. The Dutch-inspired Gambrel roof is a Dorchester County rarity. John Caile, who was leasing the property, used English “ballast” bricks laid in Flemish bond to create this Georgian-style home sometime before 1763. It has undergone regular remodellings over the years but retains much of its original appearance and detailing.

Le Compte House
204 High Street

The Le Compte (translating roughly to “the Count” in French) family in Dorchester County descends from Antoine LeCompte who explored the coastal land of the Great Choptank River in the late 1650s and settled around a bay, later known as LeCompte Bay. This three-bay Federal style brick house was built in 1803. The stone double keystone lintels over the windows are a tip-off of the owner’s affluence.

Bayly House
207 High Street

The core of this house dates to 1755 and is considered the oldest in Cambridge. It was owned there by John Caile who took it apart, shipped it across the Chesapeake and re-assembled it in Cambridge. Today’s appearance is attributed to Alexander Bayly in the mid-19th century.

Mexican War Bell
Dorchester County Courthouse, southeast corner of High Street and Court Lane

This bell was cast in 1772 and hung in a monastery in Mexico before being brought to America during the Mexican War in 1846. It served as the fire alarm in Cambridge until 1883. The fieldstone monument was erected in 1940 by the Dorset Chapter of the National Society Daughters of the American Revolution.

Dorchester County Courthouse
206 High Street  

This Italianate-influenced courthouse was constructed in 1853. It was designed by English-born Richard Upjohn, who became most famous for his Gothic Revival churches in the 1840s and helped foster the Italianate style in America. He was a founder and the first president of the American Institute of Architects. The Cambridge courthouse is the only one Upjohn did in Maryland. Another architect of repute, Charles L. Carson of Baltimore, also contributed work on this site. He designed the County Jail, a Queen Anne and Romanesque Revival style granite structure with brick and terra cotta features, which stood to the southeast of the courthouse from about 1882 until its demolition in 1994. 

Christ Episcopal Church
northwest corner of High Street and Church Street

The Episcopal Church of Great Choptank Parish has served the community since 1692. Originally parishioners worshiped in the Court House. With the help of tobacco taxes and the authority of King William, the construction of the first church building was completed in 1694. The present building, dedicated in 1884, is the third to be located on this site and stands as one of the outstanding examples of Gothic architecture on the Eastern Shore and the State of Maryland. It was designed in green serpentine stone by noted Baltimore architect Charles E. Cassell on a cruciform plan. The adjoining cemetery is enclosed on three sides by a brick wall, and burials therein date from 1674 to the present. Church parishioners included five governors of Maryland, a state Attorney General, an Ambassador to the Netherlands, local judges and lawyers and several U.S. Congressmen, a number of whom are buried in the adjoining cemetery. The Maryland governors are: John Henry (1797-98), Charles Goldsborough (1819), Henry Lloyd (1885-88), Phillips Lee Goldsborough (1912-16), and Emerson C. Harrington (1916-20).

Cambridge Post Office
301 High Street  

This Neoclassical building dates to 1917 and reflects an attempt by the United States governmentin the first part of the 20th century to provide local communities with architecturally significant buildings.                     

303-309 High Street  

This commercial building of two shades of brown brick is typical of the downtown look of Cambridge in the early 1900s. Although renovated on the ground story, the upper stories are unchanged. 

National Bank of Cambridge
304 High Street 

Established in 1880, The National Bank of Cambridge is the oldest chartered bank in Dorchester County, Maryland. During the Great Depression of the 1930s it was the only bank on the Eastern Shore to pay depositors in cash throughout the crisis. It remains a locally owned and operated independent community bank. After the Great Fire of 1892 destroyed most of this block, J. Benjamin Brown designed this exuberant Romanesque headquarters of brick and granite. Brown was a local lumber mill owner who branched out to design and construct buildings. Among them were the Grace United Methodist Church, the local Masonic lodge and many commercial and residential properties. Brown won the first mayoral election in Cambridge after it organized under the 1882 charter. A popular leader, he served two terms but decline more.   

Fletcher Mansion
308 High Street  

Built of brick and richly ornamented, this is one of the finest Queen Anne-style houses in Cambridge and looks much the same today as it did when constructed in the 1880s. On the northwest corner is an elaborate three-story polygonal tower with round arched windows, small dormers with pointed arched windows and a finial at the peak. The heavy cornices of the tower and roof are decorated by a series of carved brackets.

Farmers and Merchants Bank
323 High Street, northwest corner of Locust Street  

This corner building constructed for the Farmers and Merchants Bank features brick above concrete construction. The design blends simplicity with traditional ornamentation. Bricks are used for decorative touches such as belt courses and lintels; however, there is no cornice.

Richardson Maritime Museum
401 High Street 

This brick building, with an odd blend of Romanesque windows and Neoclassical cornice and second floor, began life in 1908 as Maryland National Bank. Today it houses the Richardsonian Maritime Museum, the legacy of master boat builder Jim Richardson. It was founded just after his death in 1991 for the purpose of preserving the artifacts, honoring the people, and passing on the skills associated with the Eastern Shore wooden boat building heritage. The Museum houses over 40 detailed wooden boat models.

Sycamore Cottage
417 High Street 

Sycamore Cottage was built possibly as early as 1765. The house is a one and one-half story gambrel-roofed frame structure. Remodelings during the 19th century include adding Victorian windows, a central Colonial Revival entrance porch, 1840s Greek Revival interior decorative detailing, and the addition of a large one-story meeting hall. It was moved to this location in 1840. Since 1922, Sycamore Cottage has been the headquarters of the Cambridge Woman’s Club.


Arcade Theatre
515 Race Street

The Arcade opened in the 1920s and was operated by the Schine’s circuit, one of several theaters in Cambridge. The Arcade operated into the 1950s. In the 1960s, the theatre was renamed the Dorset and operated as such into the early 1970s. In the intervening years the theater has been gutted and served a number of business uses.


Skinner & Brothers Grovery
507 Race Street 

A plain brick facade partially obscures the front of a building once occupied by Skinner & Brothers grocery store. The advertisement still visible in the bricks on the side was for Lorillard’s Sensation tobacco, a popular low-cost cigarette during the Depression.

Grace United Methodist Church
501 Race Street 

A Methodist society was formed in Cambridge in the late 1700s. On May 1, 1863, 48 Methodists from Cambridge joined together to organize a new church, the charter members of Grace Methodist Episcopal Church. They met in a “neat but small” wooden structure loaned by a Presbyterian Church that never really took root in Cambridge. In November 1881, land at the corner of Race and Muir Streets was purchased from the estate of Dr. Handy, a contractor and church member. He and J. Benjamin Brown took on the task of building the present sanctuary building. The church opened for services in August 1883, in what was called a “model of architectural beauty and symmetry.” The original gray stone exterior of the church has not changed, although several additions over the years have brought the church to its present design.   

Phillips Hardware Company
447 Race Street

Born in 1868, Levi Phillips went to sea as a young man, oystering in season and sailing the West Indies trade routes at other times. At age 30 he opened a packinghouse and soon joined forces with his younger brother Albanus to form the Phillips Packing Company in 1902, canning 40 varieties of vegetables, fruit, fish and meat. During picking season the house employed more than 4,000 workers. Levi went on to be president of the National Bank of Cambridge for 32 years. The tentacles of the Phillips empire included this hardware store, currently housing artist studios. This building, and others on this block, were built shortly after a fire incinerated Race Street here in 1910. The style of these buildings is similar and is probably the handiwork of J. Benjamin Brown. Prior to the fire, Phillips Hardware was located across the street. The building is little altered since its construction.    

444-448 Race Street 

This large three-story building, like the adjoining McCrory’s Building, retains the character of its upper floors with decorative brickwork. Here, a large pressed tin cornice, typical of commercial buildings of the early 1900s, stretches across the nine bays. The ornamental oval windows originally featured opaque colored glass when it was built. 

1911 Building
431-433 Race Street 

This three-story brick commercial structure was built immediately after the Race Street fire; it has served many retail masters over the years, including a shoe store and hair stylist.  


Hopkins Building
521 Poplar Street 

The Hopkins Building, with its variety of architectural details, is one of the finest commercial structures in Cambridge and remains almost unchanged from its construction around the turn f the 20th century. Over the second-story center window is an elaborate molded ornamentation and above the two end windows are ornamental swags. The egg-and-dart motif occurs frequently as a border molding. The other commercial properties on this side of the street date to the same time but have probably been altered to a greater degree.  


Cambridge District Court House
310 Gay Street 

Now a government services building, the imposing grey masonry structure began life as an armory.

Municipal Building
305 Gay Street

Cambridge born-and-bred James Wallace was trained in the law and member of the Maryland house of delegatesin the 1850s. After the outbreak of the Civil War, he helped raise the First Maryland Volunteers (Eastern Shore) in August 1861 and took command as its colonel. The unit was intended to protect Union interests on the Eastern shore and elsewhere in Maryland but in July 1863, the First found itself at Gettysburg fighting on the third day of the battle around Culp’s Hill. In the regiment’s only day of pitched battle during its entire service, and with Wallace in command, it met and mauled the First Maryland Regiment of the Confederate States Army that contained many of their friends and neighbors from coastal Maryland. The regiment, and its colonel, ended its enlistment and mustered out two days before Christmas in 1863. By the late 1800s Colonel James Wallace began packing oysters. He was the first to start raw shucking and steam packing of oysters in Cambridge, building, with his son, a nationally known business. The Wallace family mansion stood here on heights known as “The Hill.” The property was acquired in 1838 and remained in the family for 70 years. The City purchased the mansion in 1940 and eventually razed it for office space and the Rescue Fire Company. The Colonial Revival building was erected in 1949, dominated by a three-tier tower. The first tier is made of brick with stone quoins embellishing the corners. There is a balustrade with turned spindles around the upper edge of this tier. The second tier is also wooden with a spindle-turned balustrade. Above this is an octagonally-shaped tier with tall, narrow arched openings.

Wallace Office
301 Gay Street

From this small office James Wallace could keep track of the goings-on in his packing house below. he also used the office as his headquarters during the Civil War. 


Court Lane offices
119-121 Court Lane 

This was part of the land sold by the Commissioners of Cambridge to William Bond Martin in 1811, for $165. The small office buildings on Court Lane are compatible in scale, with the exception of 513 which was renovated in the late 1800s. Decorated with Greek Revival details, they are significant as some of the earliest surviving commercial structures in Cambridge.