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Whether your interests lean towards history, nature, architecture, or the sea, springtime provides a great opportunity to get outside, and enjoy some exercise and fresh air by exploring Boston’s many historic walking trails.
Each trail focuses on a specific theme, and provides walkers with a unique view into what makes Boston special; some are maintained by federal or local parks departments, while others are maintained by non-profit organizations. All offer a free way to get to know the city. Free maps and extensive background information for self-guided tours are available online for most of these walks, and guided tours (with a fee) can usually be booked via the appropriate website, if available.
Our favorite trails around Boston include:
The Freedom Trail
This is probably Boston’s best-known historic walk. Starting at the Boston Common, its red stripe covers a 2.5-mile route past 16 of Boston’s most important Revolutionary War landmarks. Generations of school kids and visitors have followed the Freedom Trail to see the site of the Boston Massacre at the Old State House, several famous burying grounds, historic churches such as Kings Chapel, the Old South Meeting Hall where the Boston Tea Party started, the Old North Church, the Paul Revere statue in the North End, “Old Ironsides,” and the Bunker Hill monument in Charlestown.
The Emerald Necklace
Designed by Frederick Law Olmsted, who also designed New York City’s Central Park, the Emerald Necklace is a 7-mile long series of connected greenways that stretches through many of Boston’s well and lesser-known neighborhoods. Many trekkers begin at the Boston Common and the Public Garden, and follow the path through the Commonwealth Avenue Mall, the Back Bay Fens, the Riverway (home of the Muddy River), Jamaica Pond, and Harvard’s famous Arnold Arboretum, before ending in Franklin Park.
While you can certainly walk only a section of the Necklace, consider packing a lunch and taking the better part of a day to get outside of downtown, and see a different side of the city. Subway stations are easily accessible along the way, and at both ends of the Necklace to help return you to where you started.
The Boston Harborwalk
One of Boston’s newest walking trails, the Boston Harborwalk is still a work in progress. Its vision is to connect East Boston, Charlestown, North End, Downtown, South Boston and Dorchester by following the edge of Boston Harbor. As the waterfront across the city has been re-developed, the City of Boston has made it a priority to open up the waterfront for public access including walkways in front of some of the city’s fanciest hotels. The section connecting the North End to the area near the New England Aquarium offers wonderful views of the harbor, the Coast Guard Station, and Boston’s ever-changing skyline.
And Many More
Many other wonderful walks are available in and around Boston including:
The Charles River Esplanade
The Rose Kennedy Greenway
The Black Heritage Trail
The Irish Heritage Trail
Boston Women’s Heritage Trail
The City of Boston maintains a Boston Walks and Trails page that has even more information and walk suggestions, and the non-profit, Boston by Foot offers a number of fee-based guided tours that combine history and architecture.
Mary Turner is the publisher of Travel with Teens and Tweens, a family travel blog that provides reviews, resources and inspiration for families planning vacations, college visits, sports tournament travel, service trips and local daytrips with kids ages 10-19. A long time Boston-area native, Mary and her family enjoy exploring New England’s many attractions — both on and off the beaten path!
For more on the Greater Boston area, including where to stay, what to see, and what do to, click here.