Best trail running trails in Boston, Massachusetts

1,190 Reviews
Explore the most popular running 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 trail running trails in Boston, Massachusetts
Top trails (15)
#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 - Boston Harbor and Castle Island
Marine Park
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Length: 2.2 mi • Est. 55 m
This is a great, family-friendly, paved walk around a causeway to a historic fort that you won't want to miss. This is a very beautiful area just south of Boston. You will walk around an enclosed bay past a beach, a WWII memorial and then to one of the country's most famous forts which was built to defend the city of Boston. The lawn around the fort is also perfect for a picnic lunch. Keep your eye out for planes overhead (close overhead) from Logan airport as well as kiteboarders zooming around in the bay. Accessibility: The trail surface is paved and typically at least six feet wide. The terrain is gentle, all estimated to be a 3% grade or less. It will likely be navigable for most wheelchair and stroller users.Show more
#3 - 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
#4 - Jamaica Pond
Olmsted Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(102)
Length: 1.5 mi • Est. 38 m
#5 - Public Garden Monument Walking Tour
Boston Public Gardens
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Length: 1.1 mi • Est. 27 m
Monuments, sculptures beckon in Boston Public GardenShow more
#6 - Millenium Park
Cutler Park Reservation
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Length: 3.6 mi • Est. 1 h 33 m
#7 - Boston's Emerald Necklace Trail
Boston, Massachusetts
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Length: 32.5 mi • Est. Multi-day
Discover Frederick Law Olmsted's famous system of parks on this bicycle tour of the historic Emerald Necklace. From the shaded boulevard on Commonwealth Avenue to the popular shores of Jamaica Pond to the winding paths of the Arnold Arboretum, this chain of gardens, reserves, and open space serves as an oasis in the middle of a bustling city. Show more
#8 - Spectacle Island Perimeter Trail
Boston Harbor Islands National Recreation Area
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Length: 1.9 mi • Est. 46 m
This historical island is over 100 acres with over 5 miles of walking trails. Visitors must take a ferry to the island.Show more
#9 - 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
#10 - Commonwealth Ave Monument Tour
Boston, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(39)
Length: 2.2 mi • Est. 54 m
A beautiful walk from Hereford Street to the Public Garden This guide will take you on a stroll through the history of the United States. You will pass nine different monuments commemorating events and people that changed the history of both the city of Boston and the nation. Take the time to click on each of the informative links attached to this guide for a thorough description of each monument. You will start near the Fenway exit off Storrow Drive and end up at the Boston Public Garden downtown a mile later. The Commonwealth Avenue Mall is the narrowest section of the Emerald Necklace Path in Boston and connects the Public Garden downtown to the Fens. If you are interested in further exploration, check the Public Garden Monument tour at EveryTrail.com for which there is a link.Show more
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