Connect with Black history between Boston and Portland with these curated day-trips.

New England Black History Road Trip Itinerary

For much of New England, Black history is as long a history as colonization. As long as there have been Europeans, there have been people of African descent. Most of that history is largely untold and under-appreciated, but there are many people, businesses, and organizations across the six New England states sharing these stories. 

This itinerary includes four cities. There are two ways you can visit all these sites:

  1. Driving to all four cities in a row only takes about two hours cumulatively. 

  2. To do it car-free, you can treat this itinerary as a series of roundtrips from Boston.

You don’t need more than a day in each city to follow this itinerary, but you may want to give yourself more time to appreciate each place. Some of these activities are available year-round, but to enjoy them all, plan your trip between late May and late September.

 

1️⃣ Boston, Massachusetts

✈️ 🚈 If you fly into Logan Airport, you can easily take the MBTA silver line directly into the city.

First up: the Abiel Smith School and African Meeting House in the Beacon Hill neighborhood. They are managed together by the Museum of African American History. You buy a timed ticket in advance for access to exhibits in the 1835 school building, which you’ll enjoy as you wait for your guide to take you over to the meeting house. The guide will regale you with a seated presentation, then take you into the historic meeting house space itself, which is the oldest standing Black church in the United States.

The other thing to book in advance is a free ticket on the Boston Black Heritage Trail walking tour, guided by National Park Service rangers of the Boston African American National Historic Site. Better known today as a collection of mansions and row houses for wealthy white Boston Brahmins, Beacon hill of two hundred years ago was home to a thriving Black community. This 90-minute tour visits the homes and gathering places of some of their leading figures. It is not offered every day of the week or every month of the year, so if you’re here on an off-day or in the off-season, check out the self-guided version available as an audio tour on the same website. You might even consider the Park Service’s other free audio tours, many of which overlap with Black history.

Either before or after your visit to Beacon Hill, check out the exhibit at Faneuil Hall. A short walk from Beacon Hill, entering the building’s first floor you’ll find information displays and artifacts detailing the city’s connection to slavery and the slave trade in the colonial era. More in the basement. The building is open every day.

🚗 🚈 If you’re doing this tour as a road trip, go pick up your rental car and head across the Tobin Bridge. If you’re using this itinerary as a series of day trips, head either to North Station or South Station.

 

2️⃣ Newburyport, Massachusetts

🚗 🚈 Driving from Boston takes about 50 minutes.  You can also take the MBTA Newburyport/Rockport Line commuter rail from North Station. Trains in either direction leave every couple of hours throughout the day.  From the Newburyport station, you probably want to take a cab into the center of the city.  It’s only a mile and a half, but there aren’t sidewalks the whole way.

When you walk on the brick sidewalks of Newburyport, you are returning to a time before highways or railroads — when international shipping was king. Playing a major role in this and other industries was a thriving Black community. The Newburyport Black History Initiative in 2023 and 2024 erected eleven informational signs, focusing largely on everyday people, mostly in the 19th century. Checking them all out, you’ll find Newburyport to be a supremely walkable city with lots more to experience while you’re there. The Initiative’s website offers a downloadable PDF map, supplementary videos, and other links to round out the experience.

 

3️⃣ Portsmouth, New Hampshire

🚗 🚌 Driving from Newburyport to Portsmouth only takes about 30 minutes. To take transit from Boston, get a roundtrip ticket from South Station on the C&J bus; they offer multiple departures in either direction daily to/from the Portsmouth Transportation Center. From there, either take the local bus or a taxi downtown.

Here’s another small, walkable, New England port city. Your top priority is booking a guided walking tour ahead of time with the Black Heritage Trail of New Hampshire. On their website, look for the guided tours offered by Sankofa Scholars, May through November. The dates are pretty sporadic, but generally there are one or two a week in the summer months. And amazingly enough, these scholars have put together eleven 90-minute tours on varied Black history topics in this one city of 22,000 people! The tours generally start in the afternoon from their gift shop and visitor center at 222 Court Street.

If you’re there on an off-day, you’ve got two options. They offer an affordable private tour option that you schedule with them ahead of time. You can also download their PDF map of 24 Black History Trail plaques throughout Portsmouth. To really get your learning on, take this book with you: Portsmouth Black Heritage Trail: A Self-Guided Walking Tour of Portsmouth, New Hampshire by JerriAnne Boggis and Valerie Cunningham. Order it online in advance or buy it from the gift shop, then take it with you as you walk amongst the tour stops on your own.

And if it doesn’t come up on your tour, visit the African Burying Ground Memorial on State Street and take some time to appreciate the space. It’s close to the Heritage Trail visitor center.

 

4️⃣ Portland, Maine

🚗 Portland is an hour’s drive from Portsmouth. 

🚈 🚌 From Boston, you have two easy transit options: the Concord Coach Lines bus from South Station is quicker and cheaper (and they show you a movie) or the Amtrak Downeaster train from North Station takes longer and costs more money (but it's classier). Both arrive at the Portland Transportation Center, so from there, either take a bus or taxi downtown.

Portland is bigger than Newburyport and Portsmouth, but still small and walkable. Of course the top priority (tootin’ our own horn here) is taking a guided Black History Walking Tour with me at Portland by the Foot. (!) If booking well in advance, you’ve got your pick: morning or afternoon, 7 days a week, April through November. Availability tends to narrow considerably as dates draw near, particularly in September and October, but the tour is available year-round as a private group option as well. Prepare for two hours of amazing storytelling, including many historic figures of international significance!

You’ll also want to explore the Portland Freedom Trail while you’re in town. The Black History Tour I guide visits about half of those locations to explore them more deeply. That leaves many more to explore on your own! The downloadable PDF brochure lists thirteen history markers, but two more have been added since that brochure was designed: one at 32 Union Street and another at the corner of Congress Street and North Street.

 

➕ Black History in New England Beyond This Itinerary