The Black Side of Boston

The Black Bucket List hits up Beantown and the surrounding area, exploring New England's rich black history.


Eager to learn more about this era of history, I decided to take a self-guided walking tour of Boston’s Black Heritage Trail, an excursion organized by the National Park Service. In all it has 14 stops, each of them a venue of significance in the city’s African-American history.

A Hub of Abolitionists and Activists

Starting with the 54th Regiment Memorial, the trail winds through the streets of the city’s vaunted Beacon Hill neighborhood for 1.6 miles. It took me around three hours to complete the tour; taking the time really helped me put into context the city’s early black history and the characters who shaped it.

As I followed the trail, using a Park Service brochure and map, I was thrilled to learn of Boston’s unsung black activists. One stop, a house at 66 Phillips Street, is now a private residence, but in the mid-1800s it was a hub of anti-slavery and the home of Lewis and Harriet Hayden, both escaped slaves. The couple frequently held abolitionist gatherings. They also sheltered escaped slaves before helping them gain passage across the Canadian border.

A few blocks away, at 86 Pinckney Street, was the home and occasional barbershop of John J. Smith. An outspoken critic of slavery, Smith turned his barbershop into a meeting place for community organizers and abolitionists.

Wandering through Holmes Alley, a narrow passageway, I could almost feel the ghosts of runaway slaves hiding in the stairwells, with their angry masters in hot pursuit and the hushed voices of the Underground Railroad patrons in the background.

One highlight of the tour is the African Meeting House, a towering brick building with four oversize arched windows. Constructed in 1806, mostly by black laborers, it was the first African Baptist church of Boston. Besides serving as the black community’s main spiritual center, it was the center for educational and cultural activities and political meetings.

A long list of prominent abolitionists, led by Douglass and William Lloyd Garrison, took to the pulpit here. And when locals began to organize the 54th Volunteer Regiment to help thwart the Confederate Army, the meetinghouse was used as a recruitment center.

Black history also hangs heavy in the Abiel Smith School, located next door. When Boston’s growing black families needed a place to educate their children, this compact brick building became the first public school built for blacks in the country. Opened in 1835, it was the educational center for all black schoolchildren.