Best Hiking Trails in Massachusetts | Trailmonger

About hiking in Massachusetts

Massachusetts has 5,800 named trails tagged for hiking on the map, covering 5,608 miles, an average of 1.0 mile each. The longest is Bay Circuit Trail in Middlesex County, at 92.0 miles. 122 run 5 miles or longer. 14 of the state's counties have at least one; Middlesex County has the most, with 1,248 trails.

Top 100 hiking trails, longest first

Bay Circuit TrailHikeMiddlesex County92.0 mi Midstate TrailHikeWorcester County90.0 mi hikingHikeHampden County67.8 mi The Cape Cod WayHikeBarnstable County60.6 mi Metacomet - Monadnock TrailHikeFranklin County46.4 mi Boston HarborWalkHikeMTBSuffolk County45.8 mi YellowHikeMTBMiddlesex County43.2 mi Corridor 71HikeWorcester County38.1 mi BCT Section 2HikeEssex County27.9 mi Warner TrailHikeMTBNorfolk County27.7 mi Mystic Link TrailHikeMiddlesex County26.4 mi redHikeMTBMiddlesex County25.3 mi Robert Frost TrailHikeHampshire County25.3 mi Plymouth Wishbone TrailHikePlymouth County25.1 mi NET/M&M Trail (white)HikeFranklin County24.7 mi BlueHikeMTBMiddlesex County22.9 mi NET/M&M Trail (white)HikeMTBHampden County21.7 mi BCT 10HikeNorfolk County20.0 mi North Central PathwayHikeMTBWorcester County19.6 mi BCT Section 3HikeEssex County19.6 mi Assabet River Rail TrailHikeMTBMiddlesex County19.3 mi East-West TrailHikeWorcester County19.1 mi Taconic Crest TrailHikeBerkshire County19.0 mi Circuit Trail Bedford (Outer)HikeMiddlesex County17.5 mi Groton TourHikeMiddlesex County16.9 mi Mahican-Mohawk Trail (M-M)HikeBerkshire County16.8 mi BCT Section 14HikePlymouth County16.2 mi BCT 7 Lincoln/WaylandHikeMiddlesex County15.8 mi West Groton TourHikeMiddlesex County14.5 mi BCT Section 13HikePlymouth County14.2 mi Skyline TrailHikeNorfolk County14.1 mi Harvard Snowmobile Club TrailHikeWorcester County13.5 mi Pine Barrens PathHikePlymouth County13.5 mi Cape Cod Canal BikewayHikeMTBBarnstable County12.9 mi BCT 12HikePlymouth County12.8 mi Town of Barnstable Main TrailHikeBarnstable County12.7 mi Mass Central Rail Trail -- WaysideHikeMTBMiddlesex County12.6 mi BCT Section 1AHikeEssex County12.6 mi Red TrailHikeMTBBristol County12.2 mi State Forest Bike PathHikeMTBDukes County12.1 mi South Groton TourHikeMiddlesex County11.7 mi North Brookfield Rail TrailHikeWorcester County11.6 mi Moraine TrailHikeBarnstable County11.3 mi White TrailHikeMTBMiddlesex County11.2 mi Western GreenwayHikeMiddlesex County11.2 mi BCT 11HikeBristol County11.1 mi Boston Boundless Trail Section 1HikeSuffolk County10.9 mi Reservoir TrailHikeMiddlesex County10.7 mi Robert Frost Trail (Orange)HikeMTBHampshire County10.3 mi BCT 5a & 6 Billerica/Bedford/ConcordHikeMiddlesex County10.3 mi Norwottuck Rail TrailHikeMTBHampshire County10.3 mi NET/M&M Trail (white)HikeMTBHampshire County10.0 mi Blue TrailHikeMTBBristol County10.0 mi Walking City Trail Section 1HikeSuffolk County9.7 mi Mother Loop TrailHikeMTBBerkshire County9.5 mi Battle Road TrailHikeMiddlesex County9.5 mi Robert Frost Trail (Orange)HikeFranklin County9.4 mi BCT section 4HikeEssex County9.3 mi BCT 6 Acton/ConcordHikeMiddlesex County9.2 mi Skyline TrailHikeMiddlesex County9.2 mi Groton Town Forest Race 9.5 mile LoopHikeMiddlesex County9.0 mi Tully TrailHikeFranklin County9.0 mi Main Trail (blue)HikeMTBMiddlesex County8.9 mi Blue TrailHikeMTBNorfolk County8.8 mi Jones Nose to SummitHikeBerkshire County8.2 mi Huckleberry Trolley LineHikeHampden County8.1 mi Thoreau’s FootstepsHikeBerkshire County8.1 mi Polpis Bike PathHikeMTBNantucket County8.1 mi Blue Heron TrailHikeMTBNorfolk County7.8 mi Quinebaug Valley Rail TrailHikeMTBWorcester County7.7 mi East Groton TourHikeMiddlesex County7.7 mi Burbank TrailHikeBerkshire County7.5 mi Whitehall Yellow TrailHikeMTBMiddlesex County7.4 mi Rock Circuit TrailHikeMiddlesex County7.3 mi Primary TrailHikeMiddlesex County7.2 mi Father Loop trailHikeMTBBerkshire County7.2 mi South River TrailHikeMTBPlymouth County7.2 mi Rounds Rock TrekHikeBerkshire County7.1 mi Red TrailHikeMTBMiddlesex County7.0 mi Indian Head River TrailHikePlymouth County7.0 mi hikingHikeBerkshire County6.9 mi Charm Bracelet TrailHikeWorcester County6.9 mi Circuit Trail Bedford (Inner)HikeMiddlesex County6.9 mi Blue TrailHikeMTBWorcester County6.9 mi BCT 7 First Drumlin Route (LincolnWeston/Wayland)HikeMiddlesex County6.8 mi Ken Cuddeback TrailHikeHampshire County6.6 mi October Mountain Loop TrailHikeBerkshire County6.6 mi Walking City Trail Section 4HikeSuffolk County6.5 mi ACROSS Lexington Route FHikeMiddlesex County6.5 mi Mount Hunger ViewsHikeWorcester County6.3 mi Bellows Pipe TrailHikeBerkshire County6.3 mi Southwick Rail TrailHikeMTBHampden County6.2 mi Yellow TrailHikeMTBWorcester County6.2 mi Agawam River TrailHikeHampden County6.1 mi Town of Barnstable South LoopHikeBarnstable County6.1 mi NET Trail (white)HikeFranklin County6.1 mi Cross Fells TrailHikeMiddlesex County6.0 mi Pilgrim LoopHikePlymouth County6.0 mi Grand Trunk TrailHikeMTBWorcester County5.9 mi Town Forest Loop TrailHikeMiddlesex County5.9 mi

Hiking Trails by county

Middlesex County

Worcester County

Berkshire County

Barnstable County

Hampshire County

Plymouth County

Franklin County

Nantucket County

← All of Massachusetts

Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt August 28, 2026.