The Best Walking Trails & Tours In Boston MA

Boston Common Walk: 139 Tremont St, Boston, MA 02111
Much as maple syrup, lobsters, and Blue Laws are woven into the New England States’ fabric, so too is the town common, or green. Upon being settled, the area adjacent to each town’s meeting house was often designated a common place; regardless of its location, this bit of land was a central feature of life in Colonial America. Some commons were purchased from indigenous inhabitants, while wealthy landowners donated others. People grazed their animals there, mustered troops, buried their dead, and disposed of unwanted items. Boston Common became manicured gardens in the late 19th century when taming the wild was de rigeur. Boston’s socialites took over and installed flower beds, fountains, and statuary. Frederick Law Olmstead, Jr. made significant renovations in the early twentieth century. Gentrification meant that animal husbandry was no longer allowed in this public space, while the hangings and military exercises stopped. Some of these traditional New England public spaces were victims of city planners as they were eliminated or bisected by city streets. 

The oldest public park in the US is located in the center of Boston and dates back to 1634. This 50-acre piece of prime downtown real estate has been the site of Colonial militia musters, anti-slavery meetings, protests, public executions, and occupation by the Redcoats lasting eight long years. Bostonians contributed to wartime efforts by planting Victory Gardens and donating the Common’s wrought-iron fencing to the war effort. Notable public figures have spoken here: Pope John Paul II, Reverend Martin Luther King, Jr, and Charles Lindbergh.

With a wide array of historical points of interest and ample space for recreation and exercise, Boston Common has something for all visitors: swan boats, playgrounds, and walking trails connecting to other trails described below.

Freedom Trail Walk: (617) 357-8300 
This 2.5-mile walk is one of 16 Millenium trails located throughout the US. This designation is given to “visionary trails that reflect defining aspects of America's history and culture.” The Freedom Trail features 16 significant historical sites dating back to the colonial period and includes museums, meeting houses, a ship, trail markers with historical data, and burying grounds. Follow the red brick line.  

Blue Hills Reservation: 695 Hillside Street, Milton, Massachusetts, (617) 698-1802
You’ll find the Blue Hills Reservation offering hikes, cross-country skiing trails, and mountain biking over 7,000 acres, just outside of Boston proper. The view from these hills provides a panoramic view of the Boston skyline. Blue Hills’ 125 miles of trails through preserved habitats is dog-friendly and features wheelchair accessibility. The trailside museum features a native animal exhibit and houses some rescued animals, including Snowy Owls. Public transit lines are nearby. Check out the Blue Hill Observatory and Science Center at the summit of Great Blue Hill. The preserve extends from Quincy to Milton, to Dedham and beyond.

Boston Harbor Islands: Welcome Center Pavilion 151 W Atlantic Avenue, Boston, MA 02110
This National Park encompasses 34 islands and peninsulas a stone’s throw from downtown Boston and offers fishing, hiking, camping, and birding, to name only a few family-friendly activities. A historic lighthouse and a Civil War-era fort bring visitors back in time. For film buffs, the Martin Scorsese film Shutter Island has a tie to these 50 square miles of natural beauty and history. There is no entrance fee for the park, but there may be a fee for transportation to and from. 

Boston Harborwalk 
Conceived and undertaken in 1984 to preserve public access to the water, this extensive trail meanders nearly 40 miles along the Boston waterfront and connects to a plethora of other Boston trails. One-of-a-kind, the Harborwalk features artworks by prominent artists, sites of historical significance, various memorials, and a musical sculpture created by the grandson of Henri Matisse. The Harborwalk continues to expand and roll with the many changes taking place in and around the city.

Public Garden Monument Walking Tour
This lovely mile-long trail is a favorite of cyclists, birders, dog-walkers, and hikers. The first public botanical garden in the US has delighted generations of visitors since its opening in 1839. Before then, the last public park established in Boston was the Boston Common, nearly 200 years earlier. It was established as a response to New York City’s public works projects after the opening of Central Park. 

Castle Island Park: 2010 Day Blvd., Boston, MA 02127, (617) 727-5290
With convenient access to public transit lines, this historic site is dog-friendly and wheelchair accessible. Visitors are invited to walk around Fort Independence via the Castle Island Loop or try the longer Pleasure Bay Loop. Bird-watching, fishing, swimming, and cycling are favorite pastimes, and like the seagulls, kids flock to the playground.

Black Heritage Trail: 14 Beacon St, Boston, MA 02108, (508) 228-9833
This trail pays tribute to the trials and triumphs of Boston’s African-American history. The oldest surviving Black church in America, the 1806 African Meeting House, is located along the route with 15 other pre-Civil War sites. Boston’s abolitionist movement and the Underground Railroad welcomed Southern Black slaves to freedom. Here, slavery was abolished in 1783 when Boston wanted to express gratitude for Black soldiers’ sacrifices in the American Revolutionary War. The trail leads walkers through the Beacon Hill neighborhood and sites of notable events in Boston’s African-American history: schools, memorials to the war dead, businesses, churches, and relevant stops in their search for survival and equality.

The Emerald Necklace Park: Shattuck Visitor Center, 125 The Fenway, Boston, MA 02115
With 1,100-acres of parkways and waterways stretching from Boston to Brookline, the Emerald Necklace is a favorite destination for locals and visitors seeking to escape the city’s hustle and bustle.  This seven-mile stretch was designed in 1870 by landscape architect Frederick Law Olmstead, designer of New York City’s Central Park. Its six parks extend from the Boston Common to Franklin Park in West Roxbury.