The original white settlement of the area near Annapolis was at Greenbury Point, although the land is now mostly covered by the Severn River. In the middle of the seventeenth century, Puritans living in Virginia were threatened with severe punishments by the Anglican Royal Governor if they did not conform to the worship of the Anglican church. Then Cecil Calvert, the second Lord Baltimore, offered the Pilgrims generous land grants, freedom of worship, and trading privileges if they agreed to move to Maryland, which he wanted to have settled. In 1649 they started a community on a site at the mouth of the Severn River on the western shore of Chesapeake Bay.

The Puritans named their new settlement Providence. In 1650, Lord Baltimore, the overseer of the colony, granted a charter to the county that surrounded Providence. He named it Anne Arundel County after his beloved wife, Anne Arundel, who had died shortly before at the age of thirty-four. But the Puritans refused to sign an oath of allegiance to Lord Baltimore, in part because he was a Roman Catholic. In 1655 he sent the St. Mary’s militia, headed by Governor William Stone, to force the Puritans into submission. A battle between the two groups took place on March 25, 1655. The Puritans won the conflict, which was the first battle between Englishmen on the North American continent. Eventually, Maryland became a royal colony.

Over time a small community began to develop on the peninsula that is the site of present-day Annapolis. It was known as Anne Arundel Town, taking its name from the county. The settlement grew and by the late 1600s the population of the province had reached nearly 25,000 residents. People started to object that the then-capital, St. Mary’s, was too far away from where the majority of the people lived. Royal Governor Francis Nicholson decided a more centrally located capital was needed and chose the site of what is now Annapolis. He named the new capital Annapolis in honor of Princess Anne, who became queen of England in 1702. It was Nicholson who determined that the city be built on a grand baroque street plan much like the great capitals of Europe. Streets were designed to radiate from a circle that was to contain the capitol. In a second circle was built an Anglican church.

Before the Revolution, there were fewer than 1,500 people in Annapolis, yet it was the center of wealth, culture, and crafts until the 1770s, when it was surpassed by Baltimore. This walking tour will begin at City Dock, the heart of the historic district and of the colonial seaport...

1.
City Dock
Dock Street

Mariners pulling up to City Dock today would see an Annapolis skyline that looks an awful lot like it did to watermen two centuries ago. Numerous shops and restaurants line the waterfront while work boats, tour boats, pleasure craft, and visiting ships mingle in the harbor. Located at the foot of City Dock, you’ll see the Kunta Kinte-Alex Haley memorial, commemorating the site where the young African, immortalized in Alex Haley’s “Roots,” was sold into slavery in the 18th century. The sculpture features a life-size sculpture of Alex Haley reading to children. 

WALK UP DOCK STREET AWAY FROM THE WATER. 

2.

Middleton Tavern
2 Market Place 

The building was probably occupied as early as 1740. In 1750, Elizabeth Bennett sold the property to Horatio Middleton who operated the building as an “Inn for Seafaring Men.” The nautical oriented Middleton also owned a ferry that linked Annapolis to the Eastern Shore of the Chesapeake Bay was an important stopping place for early travelers using the ferries. The Tavern was frequented by members of the Continental Congress - Washington, Jefferson, Franklin and others - meeting in the State House on such historic occasions as the resignation of General Washington’s commission, December 23, 1783, the ratification of the Treaty of Paris ending the Revolutionary War in January 1784, and the Annapolis Convention which laid the groundwork for the Federal Constitution Convention held the following year in Philadelphia. In addition, Middleton Tavern was the site of the first meetings of the Maryland Jockey Club in the days before the Preakness. 

3.

Market House
Main and Compromise streets 

The brick Market House dates to 1858, when it was used by sailors who docked and stocked up on supplies. According to the city charter, the building must always function as a market, just as its predecessors did dating back to 1728. 

BEHIND THE MARKET HOUSE TURN RIGHT ON PINKNEY STREET.

4. 

Waterfront Warehouse
4 Pinkney Street 

This small brick dockside warehouse is typical of the storage facilities that historically peppered the Annapolis docks. A rare survivor from those early days, this one now serves as a museum and features a replica model of the 1700s Annapolis waterfront. 

5.

Shiplap House
18 Pinkney Street 

Shiplap House was built about 1715, making it one of the oldest surviving buildings in Annapolis. The term “shiplap” refers to the exterior siding on the rear of the building, a technique used primarily in shipbuilding. Edward Smith lived there and used it as his place of business and to house “strangers.” He combined inn-keeping with the business of a “sawyer,” cutting lumber into lengths suitable for building houses and ships. Currently, Shiplap House houses the main offices for Historic Annapolis Foundation. The first floor, where a tavern room has been recreated and a exhibit of 18th-century maritime trades is on display, is open to the public on a limited basis. 

6.
The Barracks
43 Pinkney Street 

Houses like these along Pinkney Street were often rented out for soldiers to uses during the years of the American Revolutionary War (1775-1783) when there were more soldiers in the city than residents. Annapolis was the focal point for Maryland’s war effort where supplies were stored and troops gathered.. There was very little food available; the homes were meagerly furnished; and no fuel was provided. What furniture there was in the house was probably burned in an effort to keep warm. When not being used to barrack troops, this building would have been the home of a successful craftsman or artisan who lived and worked in the dock area of Annapolis in the 1770s.

TURN RIGHT ON EAST STREET. 

7.
James Brice House
42 East Street

Captain John Brice emigrated to Maryland from Haversham, England in 1698 to become a gentleman planter and merchant. The Brice House, an excellent example of Georgian five-part architecture, is distinguished by its great size, dignity and huge chimneys. It was built during the period of 1767 to 1773 by James Brice, a one-time mayor of Annapolis and briefly an acting governor of Maryland. 

TURN RIGHT ON PRINCE GEORGE STREET. 

8.
Sands House
130 Prince George Street

No one really knows exactly how old the Sands House is. Archaeologists have uncovered signs of a house built by English settlers some time in the seventeenth century and beams in the houses have been identified as being from a tree cut down in 1681. When the house was built, or rebuilt, in 1739 it received a new, more permanent fieldstone foundation. Much later, the stone was replaced with a more substantial brick foundation. The latest foundation addition was in 1904 when the house was raised nearly two feet. One of the oldest and most significant frame houses in Annapolis, the old home, a tavern between 1771 and 1798, has passed down through seven generations of John Sands’ descendants to the present owners.

TURN AROUND AND WALK BACK UP PRINCE GEORGE STREET.

9. 
Patrick Creagh House
160 Prince George Street 

The one and one-half story brick house with a steeply pitched gambrel roof was built between 1735 and 1747 by local craftsman Patrick Creagh, and enlarged during the late 18th or early 19th centuries. The site of slave auctions in the 1700s, in the early 19th century the property was purchased by John Smith, a free black man, who operated a livery out back. His wife was the proprietor of Aunt Lucy’s Bakeshop at the corner of Main and Greene Streets.

10.
William Paca House
186 Prince George Street

Constructed between 1763-1765 for William Paca, a wealthy young planter and one of four signers of the Declaration of Independence from Maryland, this a fine example of classic five-part Georgian architecture but the estate is known chiefly for its elegant gardens. Five terraces, a fish-shaped pond, and a wilderness garden await visitors to the two-acre outdoor space. Paca sold the house in 1780 as he became governor of Maryland from 1782 to 1785 and the property became part of Carvel Hall, one of the city’s most popular hotels during the 20th century. 

11.
Judge John Brice House
195 Prince George Street 

Built circa 1739 this early Annapolis brick house is a transitional abode from frame dwellings to brick townhomes. 

12.
Masonic Lodge
n
orthwest corner of Prince George Street and Maryland Avenue 

A Masonic temple was built here in 1872. The lodge rented the first floor to local shops and the second floor was used as a theater - the Annapolis Opera House. This Masons lost the building due to a foreclosure and later moved to its current location at 162 Conduit Street in 1890.

TURN RIGHT ON MARYLAND AVENUE. 

13.
Chase-Lloyd House
22 Maryland Avenue 

Although Samuel Chase, an eventual signer of the Declaration of Independence, began building this house in 1769 while he was a young lawyer, he never resided in it, for he sold it unfinished in 1771 to Edward Lloyd IV, a wealthy Maryland planter and politician. Lloyd immediately engaged architect William Buckland, newly arrived in Annapolis, to continue construction, completed three years later with the aid of local architect William Noke. The structure, one of the first three-story Georgian townhouses erected in the American Colonies, ranks among the finest of its type in the United States . Two massive interior chimneys protrude through the broad, low, hip-on-hip roof. The brick walls are laid in Flemish bond and adorned by belt courses of rubbed brick at the second- and third-floor levels. An enriched cornice embellishes the roofline. At the front, or east, facade the axial line features a tall, projecting central pavilion and entranceway, an arched window on the third floor, and crowning pediment with a small bull’s-eye window. Of particular note is the entranceway, in essentially a Palladian motif. The three-section composition was rarely used in Georgian houses before the Revolution. The door is topped by a fanlight and flanked by two panels of sidelights. The three openings are framed by two engaged Ionic columns and two Ionic pilasters which support an entablature that becomes an open pediment over the door. The triple windows on the second floor over the entrance door and the arched windows in the center of the three on the third are also unusual. 

14.
Hammond-Hardwood House
19 Maryland Avenue 

The Hammond-Hardwood House was built for the 25-year-old tobacco planter Matthias Hammond on a large site comprised of four town lots he had acquired. Hammond retained William Buckland, a joiner by trade, in 1774. By this time, 40-year old Buckland was acknowledged as one of the first architects working in the Colonies making this one of America’s first homes professionally designed from the ground up. Buckland delivered an Anglo-Palladian villa, planning and supervising its construction. The building has a fine sense of scale and proportion with its three sections, connected by hyphens, oozing sophistication inside and out. The doorway is acknowledged as one of America’s finest entries. Unfortunately, Buckland’s masterwork would be his last as he died later that year.

15. 
Lockerman-Tilton House
9 Maryland Avenue

Built in the first half of the 18th century, this house has been owned by John Rogers, first chancellor of the State of Maryland, and Josephine Tilton. Her husband accompanied Admiral Perry on the first expedition from the West to Japan. The kitchen was a separate house and was once home to Comm. Gordon Ellyson, the Navy’s first aviator. 

TURN RIGHT ON HANOVER STREET. 

16.
Peggy Stewart House
207 Hanover Street 

On October 15, 1774, Anthony Stewart’s brig the Peggy Stewart, named for his daughter, docked at the Severn River. On board were hidden 17 boxes - more than 2,300 pounds - of tea. The citizenry of Annapolis was seized with patriotic fervor and to save his cargo Stewart paid the tax on the tea, even though it was consigned to another merchant. He avowed that the tea was not his and offered to land the cargo and burn it, but the crowd was not appeased. Finally, at a radical public meeting, Stewart was forced to sign an apology for even bringing the tea to Annapolis and to pacify their indignation he set fire to his own ship. Shortly thereafter, he fled this 1763 Georgian house to England. On the campus of the United States Naval Academy across the street, on the side of Luce Hall, on Holloway Street, is a plaque marking the site of the burning of the Peggy Stewart. Thomas Stone, a signer of the Declaration of Independence, owned the house from 1783 to 1787.

TURN AROUND AND RETRACE YOUR STEPS ON HANOVER STREET. 

17.
St. Anne’s Church Rectory
215-217 Hanover Street 

This land was owned by Philip Key, great-grandfather of Francis Scott Key who sold it to the Episcopal Church in 1759. The 1760s building was maintained it as a rectory until 1885.

GO TO MARYLAND AVENUE AND TURN RIGHT TO ENTER THE UNITED STATES NAVAL ACADEMY THROUGH GATE #3. 

18.
Preble Hall
118 Maryland Avenue

The United States Naval Academy, then called the Naval School, was founded in 1845 on land purchased by the Navy Department on Windmill Point from the Dulany family. Originally it had been Fort Severn, composed of 9 acres. The original class had 50 midshipmen and seven faculty members. This area of the campus is considered the ceremonial section. Preble Hall, the first building on the left inside the gate, houses the Naval Museum that features intricate ship models dating to the seventeenth century, flags, paintings, uniforms, swords, firearms and nautical instruments.

TURN RIGHT AND CROSS THE YARD.

19.
Bancroft Hall 

Bancroft Hall is the largest building on campus and the largest single dormitory in the world. Named after former Secretary of the Navy George Bancroft, the entire brigade of 4,000 midshipmen live in 1,700 rooms here. The Beaux Arts building was designed by Ernest Flagg and built in 1901–06. It features eight wings of five stories, or “decks,” each. 

TURN RIGHT ONTO BLAKE ROAD.

20. 
United States Naval Academy Chapel
121 Blake Street 

The United States Naval Academy Chapel is one of two houses of worship on the grounds. The cornerstone was laid in 1904 by Admiral George Dewey and the dedication was four years later. The crypt of Revolutionary War hero John Paul Jones is in the back of the chapel on Blake Road. Circled around the ornate black marble crypt are remembrances of Jones’ career, including swords and paintings of his famous ships. The tomb is styled after that of Napoleon.

RETURN TO GATE #3 TO LEAVE CAMPUS AND TURN RIGHT ON HANOVER STREET. TURN LEFT ON COLLEGE AVENUE. 

21.
Ogle Hall
southwest corner of College Avenue and King George Street

Ogle Hall constructed in 1739, has been home to three Maryland State governors, the first being Samuel Ogle who rented the house in 1747. His son, Benjamin, who also became governor, moved in and later had dinner with George Washington at the house in 1773. The house survived two fires and was purchased by the U.S. Naval Academy’s Alumni Association in 1944. 

22.
St. John’s College
College Street 

St. John’s College was founded as the successor to King William’s School, a grammar school established in 1696 as one of the first public schools in America. In 1784, Maryland granted a charter to St. John’s College. The college took up residence in a building known as Bladen’s Folly (the current McDowell Hall), which was originally built to be the Maryland governor’s mansion, but was not completed. The school is noted for its Great Books Program curriculum where students complete a four-year course of study based on about 130 classic works across many disciplines.

23. 
Site of Liberty Tree
St. John’s College (in front of Woodward Hall) 

It was common practice during the American Revolution for patriots to gather under large trees that came to be known through Colonies as “Liberty Trees.” In Annapolis it was beneath a mature yellow poplar tree that was probably 200 years old at the time, located here. Late in the nineteenth century the giant tree failed to bloom and the St. John’s students decided to fell the tree with a charge of gunpowder packed in its hollow trunk. The arboreal oldster didn’t fall and the next spring bloomed again. The tree, considered the last of the trees under which the Sons of Liberty had gathered finally succumbed to a hurricane in 1999. 

TURN LEFT ON NORTH STREET. TURN LEFT ON STATE CIRCLE.

24. 
Governor Calvert House

58 State Circle 

The original home dates back to 1695 and comprises part of the present-day hotel. The Calvert family was a prominent Maryland family and lived in the house from 1727 until the American Revolution. The only governor to live in the house was Benedict Leonard Calvert who held office from 1727 to 1731. When Calvert was replaced as governor in 1731 he left Maryland and sailed for England. He died on ship and was buried at sea in 1732. Governor Calvert is credited with making significant changes to the house for optimum comfort, including a hypocaust heating system. This primitive system constructed of wood and bricks is considered one of the earliest hypocausts built in the United States. Remnants of the Calvert House hypocaust are displayed beneath a glass-floored room near the entry of the building. Fire destroyed much of the building in 1764. The remains of the house were incorporated into a two-story Georgian-style building that was used for barracks by the State of Maryland until 1784. George Washington’s stepson lived at the Calvert House in the 1770s and is thus assumed that the president may have visited the property on occasion.

25. 
Old Treasury Building
State Circle, in front of Maryland State House 

This is the oldest public building in Maryland, completed in 1737 as the Office of the Commissioners for Emitting Bills of Credit and later the Office of the Treasurer to issue paper currency. 

26.
Maryland State House
State Circle 

The Maryland State House is the oldest state capitol in continuous legislative use in America. It was begun in 1772 and finished in 1779 and, because of its convenient location, was the nation’s capital from November 26, 1783 until August 13, 1784. As such, the large brick structure on the hill was witness to the military and political conclusion of the American Revolution. Shortly before noon on December 23, 1783, George Washington walked into the Old Senate Chamber and, speaking emotionally in a short speech, resigned his commission as commander-in-chief of the Continental Army. He concluded, “ Having now finished the work assigned me, I retire from the great theatre of action; bidding an affectionate farewell to this august body, under whose orders I have so long acted, I here offer my commission, and take leave of all the employments of public life.” Several months later, after years of negotiation, Congress ratified the Treaty of Paris in Annapolis, which formally ended the Revolutionary War. The capital dome was built of entirely of wood, including pegs rather than nails. On the grounds, on the west lawn, is a statue by Ephraim Keyser of Baron Johann de Kalb who was “pierced with many wounds” leading Maryland and Delaware troops against superior numbers in Camden, South Carolina, on August 16, 1780. He died three days later.

27. 
1 State Circle 

This two-story frame structure dates to 1740. In 1997, when a five-alarm fire destroyed an adjoining building, firefighters saved this Annapolis landmark by flooding the roof with hosed water.

28. 
State House Inn
25 State Circle

The State House Inn fronts Main Street and opens onto State Circle. The portion of the historic inn that fronts Main Street was built circa 1821, possibly replacing a building constructed on the site in 1720. The second and third floors were residence of Washington G. Tuck and his family, and the first floor facing Main Street housed stores. The building survives as one of the largest and most imposing downtown commercial structures. Today, the inn has been restored and functions as a fine lodging house. 

29.
Brooksby-Shaw House
21 State Circle 

Built in the 1720s for Cornelius Brooksby, this large gambrel-roofed house was later owned by prominent cabinet maker John Shaw in 1784. After leaving the Shaw family the house became an Elks Lodge for a time before being acquired by the state of Maryland.

30. 

Robert Johnson House

23 State Circle 

The 29-room Robert Johnson House located at 23 State Circle comprises three artfully restored houses with views of the Governor’s Mansion and the State House. From the 1770s to mid-1800s, The Robert Johnson House was home to three different members of the Johnson family who were prominent officials in city, state and national government. The home was sold out of the family in 1856.

TURN LEFT ON SCHOOL STREET.

31. 
Government House
between State Circle and Church Circle 

An expansive Victorian home was begun here in 1868 on the site of two mansions from the 1700s that were sacrificed for the official residence of the governor of Maryland and his family. In 1936 the mansard roof and Victorian features were dispatched for the current neo-Georgian design that included broad gables, chimneys and Palladian windows.

TURN RIGHT ON CHURCH CIRCLE.

32. 
United States Post Office
1 Church Circle 

This Neo-Georgian building with two sets of quoins, prominent Palladian windows and a touch of Beaux Arts ornamentation, was opened in 1901.

TURN RIGHT ON WEST STREET.

33. 
Ghiselin Boarding House
28-30 West Street

Thomas Jefferson lodged here in 1783-84 during the Annapolis session of the Continental Congress, paying 5 shillings a day for a room and half that again for firewood.

34. 
Golder House
42-50 West Street

The Golder House is named after a man who kept a store here at the Sign of the Waggon and Horse until 1765 when he died from eating poisonous mushrooms. It continued operating as a tavern under several names such as the Sign of the Pennsylvania Farmer and Hunter’s Tavern.

RETURN TO CHURCH CIRCLE AND TURN RIGHT. 

35.
St. Anne’s Church
Church Circle 

The first church built here was for Middle Neck Parish, established in 1692. When Annapolis was made the state capital in 1695 an attempt was made to establish an official state church in the middle of Church Circle. The original church, the only one in Annapolis before the Revolution, was razed for a larger house of worship in 1775; the second burned on St. Valentine’s Day in 1858. The current St. Anne’s dates to 1859, designed in the Romanesque Revival style. The steeple was delayed by the Civil War and not completed until 1866. At the request of the City of Annapolis, the Town Clock has been housed in the tower since that time.

36. 
Reynolds’ Tavern
7 Church Circle

Possibly built in the 1730s, this brick building was leased to William Reynolds in 1745, who used it as a tavern. An unusual stringcourse arches over every first floor window forming a wavy line across the front. 

TURN RIGHT ON FRANKLIN STREET

37. 
Banneker-Douglass Museum
84 Franklin Street

The Bethel congregation of the African Methodist Episcopal Church acquired this property in 1874, ten years after the abolition of slavery in Maryland and raised this brick, Victorian Gothic church. The congregation was comprised of former slaves and low income parishioners who had previously worshiped in simpler frame buildings in segregated parts of Annapolis. This building, with honey oak interiors and stained-glass windows, cost $7,000 and was used for 98 years by the congregation.

RETURN TO CHURCH CIRCLE AND TURN RIGHT. 

38.
Anne Arundel County Courthouse
9 Church Circle 

The Anne Arundel County Courthouse is the third oldest courthouse still in use in Maryland. Begun in 1821 and completed in 1824, the earliest portion of the courthouse was built to provide a safe repository for County records and meeting rooms for the County Court and its officials, a use that has continued to this day. Several expansions followed. Architecturally, the 1892-95 alterations and additions to the courthouse still define its overall character. Designed by Jackson C. Gott, an important Baltimore architect, the alterations dramatically transformed the appearance of the restrained, almost flat Federal Style building into a more graceful, three-dimensional Georgian Revival structure, featuring the prominent entrance tower, corner pavilions and the second floor courtroom. 

39.
Maryland Inn
19 Church Circle 

In 1772, Thomas Hyde built the front. In the 1800s, the rear was added. The Maryland Inn has played host to presidents, governors, statesmen, and other important dignitaries since the 18th century. History shows that 11 delegates of the 1783-1784 United States Congress stayed at the inn. Benjamin Franklin and John Adams are also said to have enjoyed a pint or two here.

TURN RIGHT ON MAIN STREET.

40. 
Price House
232-36 Main Street 

Henry Price, a “free man of color,” built the brick half of Price House in the 1820s. Previously Charles Wilson Peale, the pre-eminent American portraitist of the age, operated a sign-painting shop here in his early twenties from 1763 to 1765. Price owned the property until his death in 1863. His grandson, Daniel Hale Williams, lived in the house while attending Stanton School. Later, Williams, a graduate of the Chicago Medical School, performed the first successful heart operation in 1897.

MAKE YOUR FIRST RIGHT TURN. TURN LEFT ON DUKE OF GLOUCESTER STREET. TURN RIGHT ON CHARLES STREET.

41.
Jonas Green House
124 Charles Street 

The Jonas Green House is one of the two oldest residences in Annapolis. The Greens were a family of printers who came from Somerset, England, in 1627 to settle the colony of Massachusetts. This house is named after its owner, Jonas Green, a cousin and printer’s apprentice to Benjamin Franklin. Jonas brought his new bride, Anne Catherine with him and together they moved into this house in May of 1738. At that time there was only the kitchen building (built in the 1690s) and a one story home which consisted of a family living room, dining room and hallway. Green was the publisher of the Maryland Gazette.

TURN RIGHT ON DUKE OF GLOUCESTER STREET. TURN LEFT ON CONDUIT STREET.

42. 
Masonic Lodge #89
162 Conduit Street 

The Freemasons of Annapolis organized in the 1740s; the Lodge started meeting in its current location here in 1890 and was eventually able to purchase the building in 1900. This was the site of Mann’s Tavern where twelve delegates from five states met in 1786 to discuss commercial problems of the new nation. Their call for another convention in Philadelphia to render the Government “Adequate to the exigencies of the Union” that resulted in the creation of The Constitution of the United States of America. Next door is the John Callahan House, that was built on St. John Street in the late 1700s. It has been moved twice in efforts to prevent its demolition. The home features an unusual gable-end principal façade and largely intact Georgian/Federal interior finishes.

RETURN TO DUKE OF GLOUCESTER STREET AND TURN LEFT.

43.
Joseph J. Murnane Building
169 Conduit Street 

Although it may have been constructed decades earlier this is one of the best representatives of commercial Italianate architecture in Annapolis that was popular across the United States in the 1860s and 1870s. The building, that has survived many uses over the decades, features a bracketed cornice and ornamental window hoods.

RETURN TO DUKE OF GLOUCESTER STREET AND CROSS OVER THE INTERSECTION. 

44.
Charles Zimmerman House
138 Conduit Street 

This is one of the few dwellings in Annapolis built in the Queen Anne style. Constructed between 1893 and 1897 for the leader of the United States Naval Academy band and creator of the composition “Anchors Aweigh,” the Zimmerman House is based on a design of George Franklin Barber. An architect based in Knoxville, Tennessee, Barber published numerous mail-order catalogs of elaborate Victorian-era house designs. As many as 10,000 examples of his houses were built around America with minor variations. The Zimmerman House is a close example of Design No. 37; minimal changes include an added entry vestibule and removal of the two-story side bay. Now owned by the First Presbyterian Church next door on Duke of Gloucester Street, the house has been restored through the church’s decade-long sweat equity program.

RETURN TO DUKE OF GLOUCESTER STREET AND TURN RIGHT. 

45.
Maynard-Burgess House
163 Duke of Gloucester Street

John Maynard was born a free black in Maryland about 1811 and died in Annapolis in 1875. Maynard’s life was a deeply responsible and public one. Between 1834 and 1845, he purchased and freed his wife, her daughter and his mother-in-law. He purchased this property from James Iglehart in 1847, “with buildings.” Architectural evidence indicates that what Maynard bought may have been, at least in part, an outbuilding dating to the late 18th century that had been moved to the site. During the next ten years Maynard improved the property, expanding the three-bay, story and a half structure to a full two-story dwelling with two front entrances, dormers and a massive central brick chimney. By 1860, the property had nearly tripled in value. Maynard’s family sold the house to Willis Burgess, a former boarder, in 1914 and it remained in the Burgess family until the 1990s.

46. 
Municipal Building
164 Duke of Gloucester Street

This two-story brick building occupies the site of the Assembly Rooms, built in 1765 for social gatherings, which included card games and balls. The building burned during the Civil War, while it was being used as the provost marshal’s headquarters. In the 1870s the city government moved from over on Main Street and occupied the structure, which incorporates portions of three original walls left standing after the fire. Inside, three murals depict early events in the city’s history.

47.
William H. Butler House
148 Duke of Gloucester Street 

This three-story Victorian Italianate probably dates to the 1850s. Butler, a prosperous carpenter and “free person of color,” was living here in 1873 when he won the race for city alderman from the third ward, becoming the first African American elected to public office in the state of Maryland. 

48.
Ridout House
120 Duke of Gloucester Street 

This was the home of John Ridout and Mary Ogle, daughter of Governor Benjamin Ogle. Built around 1765, the 2 1/2-story mansion is noted for its massive chimneys on either end and a gable roof. The brickwork on the street facade is laid in all-header bond; a flight of stone steps with wrought-iron handrails ascends to a Doric entrance under a simple pediment with dentils and modillions.

49. 
110-114 Duke of Gloucester Street 

John Ridout built these handsome townhouses as rental properties in 1774. The three houses are the earliest examples of English urban row house construction in America. Few of their kind still stand in England. 

50. 
St. Mary’s Church
107 Duke of Gloucester Street 

The Roman Catholic congregation in Annapolis purchased this property from the Carroll family in 1852 and work commenced on this church to replace a much smaller edifice, completed in 1822, that stood nearby on today’s elementary school building. The prominent spire on the Victorian Gothic brick church has graced the Annapolis skyline since 1879.

51. 
Charles Carroll House 107 Duke of Gloucester Street (behind St. Mary’s Church) 

This historically significant house was the home of three important generations of Carrolls: Charles Carroll the Settler, the first Attorney General of Maryland; Charles Carroll of Annapolis, and Charles Carrolton, one of four Marylanders to sign the Declaration of Independence. The youngest was born in the house that was begun in 1721 and is one of only 15 United States birthplaces of the Declaration’s signers that remain standing. Because of his Catholic faith, Charles Carroll of Carrollton was barred from entering politics, practicing law and voting. Carroll faced persecution under English rule for his beliefs, but he ensured that he and others would not longer fear such treatment when he signed the Declaration of Independence in 1776, becoming the only Catholic to sign the famous document. Carroll divided his time between his country estate at Doughoregan Manor and this house until 1820 when he moved to a townhouse in Baltimore. He lived there until his death in 1832 when he was in his nineties and the last surviving signer of the Declaration of Independence.

WALK DOWN ST. MARY’S STREET ACROSS FROM THE CHURCH. TURN LEFT ON COMPROMISE STREET AND RIGHT ON MARKET PLACE TO RETURN TO THE TOUR STARTING POINT AT CITY DOCK.