NortheastTop City Vacations

The Hunt: Boston Heritage Trails

By , November 4th, 2015

Boston is a city rife with history: as one of the oldest cities in the United States, it has been a key player in every period of our nation’s history. Nowadays modern buildings and roads mingle with nearly 500 years of historical landmarks to create a great destination to spend a weekend or longer exploring. It can be tough to know where to start, but Boston has a large selection of historical walking trails that will help you dive deep into the rich history of the city. Here are some of the best Boston heritage trails.


The Freedom Trail


The Boston Freedom Trail. Photo by Andrew Malone CC BY

Colonial Boston played a huge part in the Revolutionary War and the foundation of America. This is the most well known historical trail in town and traces that very chapter of history. The two and a half mile trail is outlined in red brick and winds its way through central Boston. Start at the Boston Common, the oldest city park in the United States and follow the trail to Granary Burial Ground, where founding fathers like Samuel Adams and John Hancock were interred.

From there, continue on to landmarks like Faneuil Hall, the site of the Boston Massacre, Paul Revere’s home, and the Old North Church. The trail ends across the water in Charlestown at the USS Constitution, a 220-year-old Navy ship christened by President Washington himself. Walking this trail will take a minimum of 2-3 hours but could also take an entire day depending on how interested you are in the various sites. The route is well marked with placards and sign markers, so you won’t need a map or guide to follow along, but if you would like more information the Visitor’s Center in Boston Common has pamphlets.

Black Heritage Trail


The Black Heritage Trail in Boston. Photo Edgar by CC BY

This trail, created by the Museum of African American History, explores the history of black Americans in 19th century Boston. It passes through homes, schools and memorials to abolitionist leaders. Unfortunately, many of the sites on the trail are privately owned and can’t be entered, with the exception of the African Meeting House and the Abiel Smith School. The walk will also take you by the Lewis and Harriet Hayden House, a famous stop on the Underground Railroad. You can explore the trail on your own but the museum also offers free-guided walking tours daily. Check their website for the schedule.

Women’s Heritage Trail

The Boston Women’s Heritage Trail celebrates the many strong women who helped shape both Boston and the nation as a whole. There are a lot of sites to cover here, so the trail is actually parsed into seven different self-guided walks that explore different neighborhoods around Boston. For example the Back Bay tour takes you to sites like the original location of Emerson College, the home of famous suffragette Julia Ward Howe and the Women’s Mural in Boston Public Library. To explore the Women’s Heritage Trails you can either buy a guidebook, or use the self guided tour information on the BWHT website. Occasionally the association also leads guided walks.

Irish Heritage Trail


Fenway Park is part of the Irish Heritage in Boston. Photo by Chase Elliot Clark CC BY

The Irish were some of the first and most prolific immigrants to Boston and this walk celebrates their many contributions to the city. The trail starts with the most famous of all the Irish families in Boston: the Kennedys. The Rose Kennedy Greenway is a beautiful 15-acre park made of reclaimed land from the Big Dig, a large construction project in town. From there, the walk continues on to landmarks like the Irish Famine Memorial, the Central Burying Grounds and the John Boyle O’Reilly Memorial. It ends at Fenway Park, one of Boston’s most famous landmarks, designed by (you guessed it) an Irishman. Check out the Irish Heritage Trail website for detailed information and a map.

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