Tips + Trends

Trail Ways: How to See Historic Boston by Foot

Boston is so packed with historic sites and monuments it’s tough to know where to start. Try these walking tours to hit the landmarks you’ve always wanted to see, along with some noteworthy spots you may not know. You’ll probably need to take a break, so we’ve also got great places to rest and refuel along the way.

Freedom Trail

Boston’s most famous historic walk takes in a wealth of important revolutionary sites and is a cinch to navigate: Just follow the red brick path. You’ll see the graves of Samuel Adams and John Hancock in the Granary Burying Ground, plus Paul Revere’s house. If you make it all the way to the end (Bunker Hill, in Charleston) you can avoid retracing your steps by taking a ferry from the Charleston Navy Yard to Long Wharf (opposite the aquarium) in the North End.

Take a break: A block from the Paul Revere House, Mike’s Pastry is an old-school Italian bakery famous for its cannoli. Just after you cross over to Charlestown, you’ll pass Sorelle Bakery & Cafe, where you can refuel with a sandwich or scone.

Black Heritage Trail

Free African-Americans living in Boston were key participants in the abolitionist movement of the 1800s. This trail winds through Beacon Hill, where you’ll pass historic homes, including the 1833 Hayden House, an important stop on the Underground Railroad. The walk ends at the Museum of African American History, set in the 1806 African Meeting House.

Take a break: Head north on Irving Street from the John Coburn House to Cambridge Street for plenty of dining options, such as pub grub at The Hill Tavern or a quick burger and fries at Griddler’s.

Irish Heritage Trail

The Irish trail celebrates the enduring impact of the large Irish-American community on the city. The trail passes through downtown and Back Bay, ending at Fenway Park, which was built by Irish immigrant Charles E. Logue. At School and Washington streets you’ll see a moving memorial to the Irish famine, which sent tens of thousands of immigrants to Boston between 1845 and 1849.

Take a break: Keep the spirit of the tour alive with a pint of Guinness at Emmet’s Irish Pub and Restaurant, near the famine memorial. Near the end of the walk, try lively Lansdowne Pub (behind Fenway Park).

Women’s Heritage Trail

The Boston Women’s Heritage Trail is a collection of seven tours celebrating influential Boston women. The Beacon Hill tour includes the home of author Louisa May Alcott, while the Downtown tour gives you a feminist perspective on monuments like Faneuil Hall, site of many important protests and suffrage meetings.

Take a break: South Boston native Barbara Lynch, winner of multiple James Beard awards, has several bars and restaurants throughout the city. Her first restaurant, No. 9 Park, serves upscale cuisine in an elegant Beacon Hill Townhouse. Sportello is a casual Italian diner.

Salem Heritage Trail

If you have time to travel beyond Boston, take the 30-minute train ride to Salem, where a red line running through the city connects such sights as the Peabody Essex Museum and the Witch Dungeon Museum.

Boston by Foot
(Infographic: Lemonly)

Take a break: The Salem Harbor will beckon and when it does, answer its call at Finz Seafood & Grill near the Salem Maritime National Historic Site. This local fave has the perfect waterside perch and its own spin on New England eats from clams to lobster.


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