Experience the best of the best with this Top 8 list of things to do and see in Portsmouth.
Walk through history and see Olde Towne’s origins and it’s continued evolution.
Plan for your visit and explore Portsmouth with the Visitor Directory.
Virginia’s historic seaport® is well-known as an epicenter of American naval and shipping history. A lesser known fact is that Portsmouth’s busy harbor also made it a major hub of the Underground Railroad. Countless enslaved Americans from southern Virginia and North Carolina, with help from Free Blacks, local spies and white sympathizers, found freedom by stowing away on ships bound for the north. This 30-minute walking tour shows how and where many of these carefully planned escapes unfolded, and reveals some of the courageous and clever individuals who led the way. Want to hear an audio of it? Portsmouth is proud to announce its newest feature- a narrated version of this 30-minute tour here.
Note: America’s Civil War Trails, LLC., has a designated Underground Railroad interpretive sign located at the the Emanuel A.M.E. Church. The church is also a prominent stop on the National Park Service’s Network to Freedom.
The first enslaved Africans to arrive in the United States docked in nearby Hampton in 1619. Soon after, Portsmouth’s harbor developed into a bustling port, as this illustration shows, with many ships lugging human cargo.
Organized resistance to slavery began immediately. The earliest allies to enslaved people in Portsmouth and across the region were the Powhatans, a native tribe with a village on Swimming Point, where the Naval Medical Center now stands. Driven from their land by British colonists, the Powhatans battled the settlers and welcomed runaway slaves into their ranks.
After northern states passed Gradual Emancipation laws in the late 1700s, sympathetic captains and crews from Philadelphia, New York and Boston became the newest allies to enslaved people in Virginia – especially in Portsmouth, where the active harbor provided cover for slaves stowing away on strategically selected ships.
A clandestine network of Free Blacks, enslaved workers, and supportive white citizens formed a shadowy coalition in Portsmouth, sharing information about northbound ships that might provide passage to freedom. The first local hub of this network (which became known as the Underground Railroad after 1831) was the Crawford House Hotel. A plaque commemorating the hotel is located at Crawford Parkway and Queen Street, where it stood for over a century. Built in 1835 across from High Street Landing, the Crawford House buzzed with maritime clientele. Eliza Bains, a Black woman who worked there, memorized schedules of northbound ships and monitored the conversations of officers and crew in order to assess the safest vessels and the safest time for stowaway slaves to board.
A decade before the Civil War, another lively hotel opened in Portsmouth – the Macon House – at the corner of Middle and North Street. When the hotel opened in 1851, the other side of North Street had not been fully developed, so there was a clear view of the harbor, making this block a prime escape hub for runaways.
According to the African American Historical Society of Portsmouth, the house at 300 North Street was a frequent hiding place for freedom seekers. A variety of ruses were used to ensure safe passage – including runaway slaves having helpers nail them into the false back of an armoire, with small, punched-in breathing holes. The armoire would be shipped north to the address of a secret Underground Railroad operator, where the tightly wedged escapee would step out into a life of liberty.
In May 1854, 22-year old enslaved woman named Clarissa Davis hid in a crawl space in this house for over two months before circumstances presented a secure plan for her to flee. Mindful of frequent police patrols – and the $1000 reward offered for her capture – Clarissa waited for a stormy night – when the streets would be empty – to make her way to a northbound ship. To further elude notice, Clarissa dressed as a man when she hustled from the house to the harbor, where she was brought aboard the City of Richmond by a pro-freedom crew member. Clarissa soon reunited with her brothers, who had previously escaped, and they began a new life in New Bedford, Massachusetts. For many decades, Portsmouth’s Underground Railroad secretly engineered countless flights to freedom, resulting in family trees branching out to this day across the U.S. and Canada.
George Teamoh was born enslaved in Norfolk, but was hired out to work in the Portsmouth shipyards, where he illegally taught himself to read and write. With the help of the Underground Railroad, he fled Portsmouth in 1853 on a ship he was working on, and like Clarissa Davis, started a new life in New Bedford. But he missed Portsmouth, and after the Civil War he returned. He later was elected as the senator representing Portsmouth in the first election in which African Americans could vote. He fought for the rights of shipyard workers, was a leading light during the Reconstruction era, and wrote a highly acclaimed memoir.
On this site stood Portsmouth’s original Emanuel African Methodist Episcopal Church, founded in 1772 – three years before the American Revolution. From the 1830s to the 1850s, this was the nucleus of Portsmouth’s Underground Railroad. Eliza Bains (of the Crawford House Hotel) and other leaders conferred at services and community events here to relay northbound ship schedules and freedom-friendly crew members. It mysteriously burned down in 1856 – “by wicked hands” – though parts of the graveyard still remain.
Just months after the original AME Church was burned down, Free Blacks and enslaved workers joined forces to rebuild the church a few blocks away. They also rebooted Underground Railroad operations. How did the new church differ from the original? It was constructed with hidden alcoves in which runaway slaves could more comfortably hide, and secret water ducts in which they could more clandestinely flee to the harbor.
After the Civil War, the blocks surrounding this church became known as Lincolnville, Portsmouth’s first African American neighborhood, which boasted a lively social scene and its own newspaper. Multiple historical markers commemorate the significance of this church in the Black community over the past two centuries.
If you’ve worked up an appetite on this tour, you can enjoy Portsmouth’s finest soul food just around the corner at District, 448 Green Street. Bon appetit!