Photo: Sean Pavone/Shutterstock

In Boston, Consider a Fresh Take on the Historic Freedom Trail

Boston Culture
by Alex Bresler Feb 25, 2020

Spend an afternoon in downtown Boston, and you may encounter a man in a waistcoat and breeches spouting facts about the American Revolution. The city’s top attraction is a set of 16 historic sites known as the Freedom Trail, and the costumed guides who herd tourists down the 2.5-mile red-brick path that cuts through northern Boston have become fixtures of the city. Impressive as their commitment to historical accuracy is, the Freedom Trail can be an opportunity to appreciate more than just Boston’s past. Consider an itinerary that loops in off-trail sites to showcase the best of the city from Beacon Hill to the North End, the colonial era to today. Follow these tips to turn your Freedom Trail tour into a full day on the town.

Start at Faneuil Hall and make a loop.

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To do the Freedom Trail start to finish, travelers typically head north from Boston Common or south from the Bunker Hill Monument, following a relatively straight line between downtown Boston and Charlestown across the river. We recommend a more circuitous route. Begin your tour at Faneuil Hall, a Revolutionary-era meeting hall and marketplace that’s filled with shops and restaurants. Grab a bite at Quincy Market to fuel up for the walk ahead, then continue on to the North End sites: Copp’s Hill Burying Ground, Old North Church, and Paul Revere House.

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Take your time surveying the North End, a neighborhood that has been lived in since the 17th century, but work in some newer landmarks too. En route to Copp’s Hill Burying Ground, stage a photo op outside Boston’s famously narrow Skinny House. After visiting Old North Church, detour to All Saints Way on Battery Street, where Boston resident Peter Baldassari has been curating an alleyway shrine to Catholic saints for years. From there, walk toward the water to find some of the best views in the city around Battery Wharf.

Photo: Caffé Vittoria/Facebook

Getting back to the trail, Paul Revere House closes out the North End sites. Around the corner, grab a cappuccino at Caffè Vittoria, said to be the first Italian cafe in Boston and a must-eat cannoli spot in Little Italy. Once caffeinated, start heading back toward Faneuil Hall, but stop by the little-known Rose Kennedy Rose Garden first. Located in Christopher Columbus Waterfront Park, it’s the perfect secret spot to rest your feet a minute.

Breeze through the next set of sites.

Photo: Sean Pavone/Shutterstock

Sixteen landmarks sounds like a lot to squeeze into a few hours. Boston was a lot smaller in its early days, however, as is evidenced by the density of Freedom Trail sites in the downtown area. Clustered together are several landmarks that you can visit in relatively quick succession, including the Boston Massacre Site, Old South Meeting House, Old Corner Bookstore, Benjamin Franklin Statue, Granary Burying Ground, Park Street Church, and Old State House.

Two other sites offer additional tours. If you have the bandwidth, take the 25-minute tour of the Old State House, the city’s oldest surviving public structure, or either the Bells & Bones or Art & Architecture tour at King’s Chapel.

Do a lap around Beacon Hill.

Photo: Sean Pavone/Shutterstock

After a big burst of sightseeing, it’s time to reward yourself with a leisurely stroll through one of Boston’s most charming neighborhoods, which begins just east of King’s Chapel. Home to the grand Massachusetts State House and some of the priciest old brick real estate in the city, Beacon Hill is a shopper’s and diner’s playground, with boutiques lining Charles Street, your choice of white-tablecloth bistros and brasseries, and cobblestoned Acorn Street’s glimpse into what early Boston might have looked like. Try Ma Maison if you’re ready for a meal.

Though the Freedom Trail serves up more than enough historic sites on its own, Beacon Hill also plays host to the Black Heritage Trail. For a different perspective on American history, head to Joy Street for the Museum of African American History, housed in the former Abiel Smith School adjacent to the African Meeting House, both of which are National Historic Sites.

Don’t stop at Boston Common.

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You may find yourself breezing through much of the Freedom Trail, but Boston Common is one site where you’ll want to slow things down and enjoy the scenery. Sharing two edges with Beacon Hill, the Common was established in 1634, and almost exactly 200 years later, the Boston Public Garden was built adjacent to it in 1837.

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Though not technically a Freedom Trail site, the Public Garden is too lovely, and too convenient, to skip. Visitors know it best for the Swan Boats that ferry passengers across the pond. There’s something to do in the parks no matter the season, be it sprawling on the grass or ice skating on the Common’s Frog Pond. Depending on when you visit, see what’s on in the city as annual events like tree lightings and the Boston Freedom Rally are held in the parks, as well.

Don’t forget Charlestown.

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Most of the Freedom Trail connects neatly from the North End to Boston Common. The final two sites are located across the North Washington Street Bridge in Boston’s Charlestown neighborhood. Though often overlooked by visitors, even some who walk the Freedom Trail, Charlestown is where the Massachusetts Bay Colony originally settled, later developing ties to Boston’s Irish and naval heritage. Here, you’ll find the USS Constitution and Bunker Hill Monument, which commemorates the first significant battle of the Revolutionary War.

Photo: Jon Bilous/Shutterstock

If you want to do the Freedom Trail in one fell swoop, it makes sense to start your tour at Boston Common and end at the Bunker Hill Monument. Time permitting, however, we recommend splitting the trail into two tours to fully appreciate both downtown Boston and Charlestown. You’re more likely to climb to the top of the Bunker Hill Monument and visit the museum at its base that way. You’ll have time for the 45-minute USS Constitution Tour. And, depending on which you visit last, you can top it off with a seafood lunch at Pier 6, right there in the Naval Yard, or get a pint and Sons of Liberty Burger at Warren Tavern, founded in 1780.

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