Best city walk trails in Boston, Massachusetts

536 Reviews
Explore the most popular city walk trails near Boston with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.
Map of city walk trails in Boston, Massachusetts
Top trails (9)
#1 - Boston's Freedom Trail
Boston Common
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(330)
Length: 2.5 mi • Est. 1 h 1 m
Discover the roots of the revolution and Boston's rich history on this popular walk. The Freedom Trail is more than a collection of historic sites related to the American Revolution or a suggested itinerary connecting Boston's unique neighborhoods. It's a chance to walk in the footsteps of our forefathers-literally, by following a crimson path on public sidewalks-and pay tribute to the figures all school kids know, like Paul Revere, John Hancock, and Ben Franklin. In history-proud Boston, past and present intersect before your eyes, not as a re-creation but as living history accessible to all. Boston played a key role in the dramatic events leading up to the American Revolution. Many of the founding fathers called the city home, and many of the initial meetings and actions that sparked the fight against the British took place here. In one day, you can visit Faneuil Hall-the "Cradle of Liberty"-where outraged colonial radicals met to oppose British authority; the site of the incendiary Boston Massacre; and the Old North Church, where lanterns hung to signal Paul Revere on his thrilling midnight ride. Colonists may have originally landed in Jamestown and Plymouth, but if you really want to see where America began, come to Boston. The Route: The Freedom Trail begins at Boston Common, winds through Downtown, Government Center, and the North End, and ends in Charlestown at the USS Constitution. The entire Freedom Trail is marked by a red line on the sidewalk; it's made of paint or brick at various points on the Trail. Timing: If you're stopping at a few (or all) of the 16 sites, it takes a full day to complete the route comfortably. If you have children in tow, you may want to split the trail into two or more days. Visitor Centers: There are Freedom Trail information centers in Boston Common (Tremont Street), at 15 State Street (near the Old State House), and at the Charlestown Navy Yard Visitor Center (in Building 5). Tours: The National Park Service's free 90-minute Freedom Trail walking tours begin at the Boston National Historical Park Visitor Center at 15 State Street and cover sites from the Old South Meeting House to the Old North Church. Check online for times; it's a good idea to show up at least 30 minutes early, as the popular tours are limited to 30 people. Half-hour tours of the USS Constitution are offered Tuesday through Sunday. Note that visitors to the ship must go through security screening. Show more
#2 - Charles River Pathway Short Loop
Charles River Reservation
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(87)
Length: 3.0 mi • Est. 1 h 13 m
This leisurely ride takes you to some of Boston's wonderful waterways, following the beautiful and historic Charles River on both the Boston and Cambridge sides as you make your way towards Boston Harbor. This tour is an excellent introduction to the paved bike paths and includes some of the best views of the city. This area is great for children and inexperienced riders. Accessibility: The trail surface is paved with asphalt and cement and typically at least 5 feet wide. The estimated grade is mostly gentle (all 5% or less) so this trail will likely be navigable for most wheelchairs/mobility equipment or strollers. There is no public designated wheelchair accessible car parking at the trailhead. The trail starts at the Charles/MGH Red Line Subway stop.Show more
#3 - Paul Revere Ride to Freedom Bike Tour
Boston, Massachusetts
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(6)
Length: 45.8 mi • Est. Multi-day
This guide takes you from the Old North Church in Boston's North End and follows Revere's ride on April 18, 1775. The Paul Revere Ride to Freedom takes you from the Old North Church in Boston's North End and follows Revere's ride on April 18, 1775 through Charlestown, Lexington and Concord. Recount the events leading up to the Revolutionary War and the great history of Massachusetts in the War for Independence.Show more
#4 - Lost Emerald Necklace Loop Trail
Back Bay Fens
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(26)
Length: 1.6 mi • Est. 39 m
Note: Some sections of the trail may be closed due to construction. Find out more information here: https://www.boston.gov/improvements-back-bay-fens-westland-avenue-gatewayShow more
#5 - East Boston Greenway
Boston, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(41)
Length: 2.5 mi • Est. 1 h 1 m
This is a nice paved path with lights. This linear trail in East Boston connects several parks including Bremen Street Park, Memorial Stadium, Belle Isle Marsh, and Wood Island Bay Marsh. It can be started at Marginal Street, Bremen Street Park, or Constitutional Beach. There is free parking on either end. Accessibility: There is paved street parking on Marginal Street at the southwest end of the trail, but it is unclear where the closest designated handicapped-accessible spaces are. There are 2 designated handicapped-accessible spaces in the paved parking lot off of Constitution Beach Road at the northeast end of the trail. Both of them are van-accessible with striped access aisles. The trail surface is paved asphalt, smooth, and typically at least 10 feet wide. The estimated grade is gentle (3% or less). This trail will likely be navigable for most wheelchairs/mobility equipment or strollers. Show more
#6 - Boston's Black Heritage Trail
Boston, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(8)
Length: 1.3 mi • Est. 31 m
The Black Heritage Trail is a 1.6-mile walking tour that explores the history of Boston’s 19th century African American community who primarily lived on the north slope of Beacon Hill. It is the largest collection of historic sites relating to life within a free Black community prior to the Civil War. Trail highlights include the 54th Regiment Memorial and the African Meeting House.Show more
#7 - Downtown Boston Kids Walk
Boston, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(7)
Length: 1.7 mi • Est. 42 m
#8 - Southwest Corridor Path
Southwest Corridor Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(13)
Length: 1.4 mi • Est. 34 m
The Southwest Corridor Park is linear park stretching from the Back Bay to Forest Hills. The park links South End, Back Bay, Roxbury and Jamaica Plain with a street-level, greenway.Show more
#9 - Melnea Cass Bike Path
Boston, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(3)
Length: 1.9 mi • Est. 45 m
This paved trail heads from the Ruggles Station to Massachusetts Ave at the intersection with Melnea Cass. There are several road crossings along the way. Accessibility: There are at least 10 designated handicapped-accessible spaces in the Renaissance parking garage lot off of Columbus Ave at the west end of the trail. All of them are van-accessible with striped access aisles. There is a fee associated with this garage. The trail is also accessible via the Ruggles Station. The trail surface is paved (asphalt, brick, cement) and typically at least 3 feet wide. The estimated grade is gentle (all 3% or less). This trail will likely be navigable for most trail goers using wheelchairs/mobility equipment or strollers.Show more