Historic Annapolis Underground Railroad Walking Tour

The Museum of Historic Annapolis is a great place to start your tour and get oriented to the history of the city, through the noteworthy exhibition “Annapolis: An American Story.” Here you will find exhibits on enslaved and free Black people who helped to build the new nation. Their labor supported lives of elegance for the stylish society. 

By the early 1800s, a growing free Black population began to shape a strong community. Some gained their freedom through manumission, others earned money and purchased freedom for themselves and others. Still others took the courageous step to find freedom by escape. 

The building at 99 Main Street, in which the Museum is located, has a unique history of its own. Built in 1790, it is a site connected to the freedom story of William “Rolla” Ross, who was enslaved by Lewis Neth. In late 1791, Neth moved his dry goods store into this building. Ross may have worked here as well as in Neth’s large house in Annapolis and on his farm. 

During the War of 1812, America’s second war of independence from Great Britain, 14-year-old Ross found refuge with the British. On the night of December 11, 1814, he escaped to the British ship HMS Menelaus, under the command of Captain Edward Dix. The ship was anchored nearby in the Chesapeake Bay. The Maryland Gazette in Annapolis reported "between twenty or thirty" enslaved people absconded on the vessel. 

An American prisoner of war, Captain Rich, saw Ross on board the Menelaus with Thomas, an enslaved man who had escaped from Henrietta Ogle. Both men were "waiting" in the cabin, likely serving as cabin staff. Lewis Neth, Jr. boarded the Menelaus, searching for Ross. Although he found him among the other refugees on the ship, Ross declined Neth's invitation to return. 

Ross escaped and was free! He joined the British Royal Navy and served until 1840. Ross lived the remainder of his life with his wife Mary and their family in Southampton, England.

99 Main Street
Annapolis, MD 21401
 

From the Museum of Historic Annapolis, head east on Main Street toward the water, past the traffic circle and to the intersection with Compromise Street. Cross the crosswalk to the opposite side of Compromise Street. Here you will see the Memorial Story Wall. Turn left and follow the Memorial Story Wall until you reach The Kunte Kinte-Alex Haley Memorial at the corner of Compromise Street and Market Space. The Kunte Kinte-Alex Haley Memorial is located there at the dock.

The Kunta Kinte-Alex Haley Memorial commemorates the place of arrival of Alex Haley’s African ancestor, Kunta Kinte, as told in the book Roots. As a symbol of resilience and hope, the memorial portrays Alex Haley’s vision for national racial reconciliation and healing. It symbolizes in Kunta Kinte and his descendants the triumph of the human spirit in very difficult times. Sculpture memorializes Haley’s vision and impact as author, descendant, teacher and storyteller. The Memorial Story Wall embodies his vision and spirit through inspirational quotes that elucidate the history and resilience of enslaved Africans arriving here in Annapolis.

City Dock
Annapolis, MD 21401

From the Kunte Kinte-Alex Haley Memorial, head away from the harbor towards Compromise Street, turn right and continue onto Market Space. When you reach Dock Street, turn left on Market Space. Make a slight right turn onto Pinkney Street where you’ll soon find the historic Waterfront Warehouse on the right, a building from the 1700s. Take a peek inside to see a model of the city, providing a bird’s eye view of the historic landscape at that time. 

Continue to 43 Pinkney Street on your left to check out Hogshead, a modest 1700s working-class dwelling. Here on weekends you can interact with reenactors in historical attire, see and handle reproduction artifacts, and compare the lives of the lower and “middling sort” with those living in the grand mansions you are about to see as you continue on this tour. 

Continue on Pinkney Street to East Street. Turn right and walk to the Brice House, crossing Prince George Street on your way. The Brice House will be on your left at 42 East Street.

James Brice was a lawyer, planter, enslaver, and a politician, whose service included interim governor of Maryland, and Mayor of Annapolis during the late 1700s. He built this elegant mansion over 7 years beginning in 1767. He and his wife, Juliana Jennings, had seven children. The home remained in the Brice family for over 100 years.

Brice kept an account book detailing the construction of his five-part Georgian house, one of the largest and most elegant of Annapolis’s historic homes surviving from colonial America. The Brice House contains evidence of the lives and skilled craftsmanship of the laborers who created the building’s structure and finishes. Many of these enslaved people continued to toil in the Brice households. Based on Brice’s account book, it is estimated that up to 28 individuals were enslaved as household staff or forced to labor in the home’s construction. 

In December, 1797, a twenty-eight-year old enslaved man named Jem escaped from Brice. According to the reward advertisement for his capture, Jem was skilled at a variety of jobs, including carpentry, gardening, carriage driving, horsemanship, and bricklaying, in addition to being a household servant. Jem’s fate after his escape is not known.

The 1802 inventory of James Brice’s property included 11 enslaved people who ranged in age from 3 to 58: Tom, Doll and her son Jesse, Nan and her sons Isaac and Nathan, Jenny and her daughter Kitty, Henny and her daughter Caroline, and a child also named Henny.

NOTE: The James Brice House is currently undergoing restoration work. Tours are not available. The house can be viewed from the street. Construction work is apparent on the grounds and the exterior of the house.

42 East Street
Annapolis, MD 21401
    

From the Brice House, return on East Street to Prince George Street. Turn right on Prince George Street and continue 210 feet. The William Paca House and Garden will be on your right.

A tour of the William Paca House and Garden provides a view into the lavish lifestyles of upper-class politicians and leaders in the mid-1700s who depended upon the work of enslaved men, women and children to maintain their ornate homes and beautifully landscaped grounds. Guided tours provide insights into the work enslaved people did during the time William Paca, one of Maryland’s four Signers of the Declaration of Independence and the state’s third Governor, lived here from 1765 - 1780. Tours also feature period furnishings and paintings and reveal the inner workings of the household.

The names of five individuals enslaved by Paca in this house are known: Denby, Affey, Poll, Sall, and Bett. At least one indentured servant fled to freedom during Paca’s ownership of the home.

The home, built by Paca in the 1760s, is now a National Historic Landmark. Visitors can also explore Paca’s two-acre colonial garden, which is a green oasis in the downtown. Terraced landscapes include native and heirloom plants, the kitchen garden, and a latticework footbridge over the fish-shaped pond to the Summerhouse. 

Thomas Jenings, a Maryland Attorney General, purchased William Paca’s home in 1780, and lived there with his family until his death in 1796. Jenings, like other wealthy elites, enslaved numerous people. His son, Thomas Jenings, Jr., was the executor and an heir to his father’s estate. On October 30, 1797, Thomas, Jr., manumitted (set free) forty-six-year old Jacob. Jacob was the lucky one.

Jenings denied freedom to the rest of his father’s enslaved people. In the spring of 1797, Thomas, Jr. advertised the sale of “Several country born” enslaved people – which meant they had been born in America. Numerous families were likely torn apart by this sale, and the fate of these individuals is not known. 

Annapolis was a trans-Atlantic slave-trading port until 1774 when Maryland abolished participation in the international slave trade. It is possible that Thomas Jenings, Sr. purchased Jacob and others directly from slave traders on ships anchored in the Annapolis harbor. Jennings, Sr. also could have inherited them from a relative or purchased them from another enslaver. 

The fates of Jacob and the other captives are not known. Jacob’s situation exemplifies manumission as one way that enslaved people gained freedom. By the early 1800s, Annapolis had a growing free Black community, largely as a result of such manumissions.

186 Prince George Street
Annapolis, MD 21401

From the William Paca House and Garden, head northwest on Prince George Street toward Maryland Avenue. The John Brice house will be on your left at 211 Prince George Street.

John Brice, III, lived at this site during the American Revolution and through the War of 1812 with his family and enslaved people. In January 1778, during the Revolution, an enslaved man named Dick escaped from Brice. Brice assumed Dick had fled with two men who had run away from Nicholas Maccubin, an enslaver who lived nearby. 

Six months later, Brice’s enslaved man named Cato escaped. Cato was African, and Brice notes in the reward notice for Cato’s capture that the man had ritual facial scarring, typical of some African tribal customs. The advertisement mentions that Cato had been brought to America when he was a boy. These men may have taken the opportunity to flee to the British, under whose protection they could have been set free in return for joining the British armed forces. 

In 1793, an enslaved man named Adam fled from Brice. It is not known whether any of these men successfully eluded capture. 

NOTE: This home is privately owned. Please be respectful of private property and do not look in windows or knock on the door. View the home from the sidewalk in the historic neighborhood.

211 Prince George Street
Annapolis, MD 21401

Continue northwest on Prince George Street to Maryland Avenue. Turn left on Maryland Avenue and continue to State Circle. Turn right on State Circle to reach the front entrance of the Maryland State House.

The Maryland State House is the place where legislation was debated and laws were passed that both defended slavery and eventually abolished it in Maryland. The Maryland legislature debated and enacted laws relating to “runaway slaves,” punishment for assisting runaways, and the rights of enslavers to recover escaped enslaved individuals. The State's governors, from their State House office, issued pardons for individuals convicted of crimes for their Underground Railroad activities. The governors also issued requisitions for the return of men charged in Maryland with assisting “runaways” who were held in other jurisdictions.

The Court of Appeals, which met in the State House, heard appeals from circuit court cases relating to the Underground Railroad. In January 1842, a "Slaveholders' Convention'' met in the House of Delegates chamber and drew up a list of twenty-five propositions for consideration by the legislature. A bill incorporating the Convention's proposals subsequently passed the House of Delegates but was rejected by the Senate.

Finally, over twenty years later, the Constitutional Convention that met in 1864 abolished slavery in Maryland on November 1st, freeing those held in bondage. This act brought the activities of the Underground Railroad to an end, when all of Maryland’s enslaved people were emancipated.

Statues of both Harriet Tubman and Frederick Douglass adorn the halls of the Maryland State House, echoing sentiments and influences from the past. The two watch over the activities of modern lawmaking and harken to a time when their fates were determined by the monumental decisions made here. The hands for Douglass’s sculpture were life-cast from those of his great-great-great grandson, Ken Morris, Jr. Douglass is shown holding a copy of the August 1862 issue of Douglass’ Monthly, which featured an article about the ‘progress of emancipation sentiment in Maryland.’

In June 1874, Frederick Douglass visited the Maryland State House. He walked in front of the painting Washington Resigning His Commission by Edwin White, which was in the Old Senate Chamber, and recited from memory George Washington’s resignation speech of December 23, 1783.

Today, you may tour the State House and view exhibits about its rich history. The State House is open everyday except Christmas and New Year’s Day. Self-guided tour information is available in the Archives Room on the first floor.

91 State Circle
Annapolis, MD 21401

Continue walking around State Circle toward the South. Turn right on School Street, then left onto Church Circle. Take the fourth left from Church Circle onto Franklin Street. Continue on Franklin Street for about 375 feet. The Banneker-Douglass-Tubman Museum will be on your left.

The Banneker-Douglass-Tubman Museum provides exhibitions on the historical and cultural experiences of African Americans in Maryland. It is named in recognition of three key African-American figures in Maryland history: Benjamin Banneker (1731-1806), Frederick Douglass (1818-1895), and Harriet Tubman (1822-1913).

Benjamin Banneker was the first African American man of science and mathematics. Banneker also protested against slavery. In a bold 1791 letter to Thomas Jefferson, Banneker compared the righteous fight for freedom by the colonists to the plight of the enslaved person in America. Harriet Tubman was a significant leader and well-known conductor for the Underground Railroad. She escaped from slavery in Caroline County in 1849, but returned approximately 13 times to rescue about 70 family members and friends between 1850 and 1860. Frederick Douglass escaped from slavery in Maryland and became a leading abolitionist and orator of his time.

In addition to offering interpretive program information about Harriet Tubman and Frederick Douglass, the Museum's permanent exhibit entitled "Deep Roots, Rising Waters: A History of African Americans in Maryland" includes special coverage of another prominent Marylander involved in the Underground Railroad: James W.C. Pennington.

The Museum is Maryland's official repository of African-American material culture and is housed in the former Mount Moriah African Methodist Episcopal Church in the heart of historic Annapolis. The church was constructed in 1874 by a congregation of free African Americans whose roots go back to 1799. The Victorian-Gothic structure was included in the Annapolis Historic District in 1971 and is on the National Register of Historic Places.

Guided tours are available for groups of 5 or more. Public programs are offered. Check the event calendar for more information.

84 Franklin Street
Annapolis, MD 21401

From the Banneker-Douglass-Tubman Museum, return on Franklin Street to Church Circle, then turn right onto Duke of Gloucester Street. Walk 0.3-mile to the second stoplight on Duke of Gloucester Street. St. Mary’s Parish School and St. Mary’s Church will be on the right. Turn right and walk the road between the school and church to their parking area. Signs mark the way to The Charles Carroll House, which will be on your left.

Charles Carroll of Carrollton, politician, planter and signer of the Declaration of Independence, was born in this home and lived here until 1821 when he moved to Baltimore. The house was built ca. 1700-1737. While domiciled here, at least two of his enslaved people escaped, including John Connor on May 8, 1787, and Adam, on August 17, 1805. Carroll was considered the largest slaveholder at the time of the American Revolution, enslaving between 400-500 people. 

He was selected as a delegate to the Continental Congress in 1776. Of all of the signers of the Declaration of Independence, Carroll was one of the wealthiest and most formally educated. He had inherited large agricultural estates that were successful due to the labor of enslaved people. He was also the only Catholic signatory on the Declaration of Independence. 

Charles Carroll served in the Maryland Senate from 1781 to 1800, and was elected as one of Maryland's inaugural representatives in the United States Senate. Carroll introduced a bill for the gradual abolition of slavery in the Maryland Senate, but it did not pass. Although he supported slavery’s gradual abolition, he did not free his own slaves. 

Before his death in 1832, he served as president of the American Colonization Society (1828-1831), which had been established as a vehicle through which free Black people could be voluntarily and involuntarily removed from America and sent to Africa. He was the last living signer of the Declaration when he passed in 1832.

The property is on the grounds of the St. Mary’s Roman Catholic Church and provides sweeping waterfront views. Tours of the house and gardens are offered on the first and second Saturdays and Sundays of the month from noon to 4 pm, June through October.

107 Duke of Gloucester Street
Annapolis, MD 21401

From the Charles Carroll House, to return to your starting point at the Museum of Historic Annapolis, return through the St. Mary’s Parish grounds to Duke of Gloucester Street. Turn left and travel on Duke of Gloucester Street for about 450 feet. Turn right onto Green Street and walk 0.1 mile to its intersection with Main Street by the Annapolis City Dock.