THE BOSTON BOUNDLESS TRAIL
Circling Boston for TK.K miles, starting and ending beside the harbor, the Boston Boundless Trail is an epic showcase of the Greater Boston Area’s natural and built wonders. It features TK green spaces and connects the City of Boston with every neighboring city and town. Scouting began in the summer of 2024, piece by piece, before the concept took off in the fall of 2025, when the Walking City Trails creators envisioned a mighty new urban hiking trail that would run through Boston and then, around it.
The Boston Boundless Trail is split into 12 sections that range from TK to TK miles each. You can also divide each of the trail sections into two shorter hikes. All the Boston Boundless Trail segments are reachable by public transportation at numerous points and they include access to small businesses and a mixof public restrooms. You can explore the Boston Boundless Trail in incremental pieces or “thru-hike” the whole thing in one circular push!
SECTION 1. COLUMBUS WATERFRONT PARK, BOSTON HARBORWALK, FAN PIER PARK, NO MAN’S LAND, DORCHESTER HEIGHTS MONUMENT, CARSON BEACH, OLD HARBOR PICNIC AREA, SAVIN HILL (T.K MILES)
Set off from the city’s far west edge on the banks of the Charles River at Millennium Park and wander through immense, rustling forests in West Roxbury to reach a series of little-known wetlands in Brookline and Chestnut Hill.
SECTION 2. SAVIN HILL BEACH, VICTORY PARK, TENEAN BEACH, NEPONSET RIVER RESERVATION, QUINCY RIVER WALK BILLINGS SALT MARSH, WOLLASTON BEACH, BISHOP PLAYGROUND, CRANE PARK (T.K MILES)
Set off from the city’s far west edge on the banks of the Charles River at Millennium Park and wander through immense, rustling forests in West Roxbury to reach a series of little-known wetlands in Brookline and Chestnut Hill.
SECTION 3. CUNNINGHAM PARK, QUINCY QUARRIES RESERVATION, BLUE HILLS RESERVATION (T.K MILES)
Experience a beautiful intersection of trees, rocks, and built elements as you summit hilltops and ramble through the woods that connect Allston/Brighton, Brookline, and Mission Hill. Climb to that exact landmark itself, before descending to Roxbury Crossing.