About trails in Berkshire County, Massachusetts

Berkshire County has 538 named trails on the map, covering 763 miles in total, an average of 1.4 miles per trail. That is the 4th largest mapped trail network among 14 counties in Massachusetts. 496 of them are tagged for hiking and 63 for mountain biking.

The longest single trail is USBR 7 (Massachussetts), at 68.5 miles. 19 trails run 5 miles or longer. Mapped points of interest in the county include 27 trailheads, 54 campsites, 46 waterfalls, 20 boat launches, and 1 rapid. The nearest towns to these trails are Pittsfield, Williamstown, and Lee.

What the trails in Berkshire County are like

By length, 344 are under a mile, 175 run 1 to 5 miles, and 19 are 5 miles or longer. 24 are loops, ending where they start; the longest is Mother Loop Trail, at 9.5 miles.

Of the 538 with measured elevation, Taconic Crest Trail climbs the most, about 7,240 ft, and 20 gain 1,000 ft or more.

Explore by activity

538All trails

496Hiking 63Mountain biking

763Total miles

54Campsites

20Boat launches

46Waterfalls

27Trailheads

1Rapids

USBR 7 (Massachussetts)MTB68.5 mi Ashuwillticook Rail TrailMTB28.0 mi Taconic Crest TrailHike19.0 mi Mahican-Mohawk Trail (M-M)Hike16.8 mi Taconic Skyline Trail14.4 mi Mother Loop TrailHikeMTB9.5 mi Jones Nose to SummitHike8.2 mi Thoreau’s FootstepsHike8.1 mi Burbank TrailHike7.5 mi Father Loop TrailHikeMTB7.2 mi Rounds Rock TrekHike7.1 mi hikingHike6.9 mi October Mountain Loop TrailHike6.6 mi Bellows Pipe TrailHike6.3 mi Washington Mountain Marsh TrailHike5.8 mi Ashley TrailHike5.6 mi Wilbur’s Clearing to SummitHike5.6 mi South Taconic TrailHike5.6 mi Busby TrailHike5.2 mi Blue TrailHikeMTB4.9 mi North Pond LoopHike4.9 mi Unverified DCR TrackHike4.8 mi Switchback TrailHike4.7 mi Beartown Mountain TrailHike4.6 mi Felton TrailHike4.5 mi Buckley Dunton TrailHike4.4 mi Wildcat TrailHike4.3 mi Aqueduct TrailHike4.3 mi Tyler Swamp LoopHike4.3 mi Sky Peak TrailHike4.2 mi Morningside LoopHike4.1 mi Mount Wilcox TrailHike4.0 mi Cheshire Harbor TrailHike3.7 mi Huckleberry Trolley LineHike3.6 mi Sara Tenney TrailHike3.6 mi Northrup TrailHike3.6 mi Schoolhouse LoopHike3.5 mi Bruiser's Pass Snowmobile Trail3.5 mi Roaring Brook TrailHike3.5 mi MinorHike3.4 mi Ashley Hill TrailHike3.4 mi Schemerhorn TrailHike3.4 mi Woodason Spring TrailHike3.4 mi Eagle Ledge TrailHike3.3 mi Hopper TrailHike3.3 mi Red TrailHikeMTB3.3 mi West Mountain RoadHike3.2 mi WhitestoneHike3.1 mi Honwee Loop trailHike3.1 mi Boulder TrailHike3.0 mi Money Brook TrailHike3.0 mi Gould TrailHike3.0 mi Tannery TrailHike3.0 mi Clam River TrailHike3.0 mi Jug End Loop TrailHike2.9 mi HonoluluHike2.9 mi RRR Brooks trailHike2.9 mi Hammertown LoopHike2.8 mi Balance Rock TrailHike2.7 mi Alander Mountain TrailHike2.7 mi Clam River LoopHike2.7 mi Boulder Trail (orange)HikeMTB2.7 mi School House TrailHikeMTB2.7 mi Yokun Ridge TrailHike2.7 mi Shaker Mountain TrailHike2.6 mi Basin Pond TrailHike2.5 mi Longview Loop TrailHike2.5 mi Pond Loop TrailHike2.5 mi Cordonier TrailHike2.5 mi Hoosic Ridge TrailHike2.5 mi Hoosac Range TrailHike2.4 mi Hickey and Peeskawso LoopHike2.4 mi CCC trail2.4 mi Blackburnian LoopHike2.3 mi Rounds Rock - Jones Nose LoopHike2.3 mi Mohawk Trail Multiuse PathHikeMTB2.3 mi Old Adams RoadHike2.2 mi Threemile Hill TrailHike2.2 mi Old Mill TrailHike2.2 mi Mohican Monument Trail (blue)Hike2.2 mi Navin TrailHike2.2 mi Veda TrailHikeMTB2.1 mi Bradley Farm TrailHike2.1 mi Yellow TrailHike2.1 mi Adam Sno-Drifters TrailHike2.1 mi Laura Lookout trailHike2.1 mi Taconic Crest TrailHike2.1 mi Bernard Farm TrailHike2.1 mi Old Taconic Skyline Trail2.1 mi Bob's WayHike2.0 mi Pine Cobble TrailHike2.0 mi Downtown LoopHike2.0 mi Beacon TrailHike2.0 mi Churchill Brook Trail1.9 mi Race Brook TrailHike1.9 mi Unmaintained trailHike1.9 mi Overlook TrailHike1.9 mi Laurel TrailHike1.9 mi WindsorHike1.9 mi Pine Mountain Trail1.9 mi Kamick TrailHike1.9 mi Class of 1933 TrailHike1.8 mi Finerty TrailHike1.8 mi Spruce TrailHike1.8 mi Mt. Prospect TrailHike1.8 mi Willow's Trail (orange)Hike1.8 mi Griffin Trail1.8 mi Haley Farm TrailHike1.8 mi Charcoal TrailHike1.8 mi Charcol TrailHike1.8 mi Balance Rock Loop Trail1.7 mi Stony LedgeHike1.7 mi Stone Hill Road TrailHike1.7 mi Old Berlin Mountain Ski TrailHike1.7 mi Red Gate TrailHike1.7 mi Burgoyne Trail1.6 mi Vagabond TrailHike1.6 mi Coakley/MainHikeMTB1.6 mi Thunderbolt Ski TrailHike1.6 mi Mills Hollow TrailHike1.6 mi Florida TrailHike1.6 mi Simon's Rock Interpretive TrailHike1.6 mi Constitution Hill TrailHike1.6 mi Round Mountain TrailHike1.6 mi Glen Meadow LoopHike1.6 mi Finerty Pond RoadHikeMTB1.6 mi October Mountain TrailHike1.5 mi Log HopHikeMTB1.5 mi Stony Ledge Ski TrailHike1.5 mi Bear ClawHike1.5 mi Lulu Brook trailHike1.4 mi Phelps TrailHike1.4 mi Edie's Way (South Loop)Hike1.4 mi Beebe TrailHike1.4 mi Daniels Brook Trail1.4 mi CCC Dynamite TrailHike1.4 mi South TrailHike1.4 mi Bob THikeMTB1.4 mi Gorilla TrailHike1.4 mi Silver Fox TrailHike1.4 mi Green TrailHike1.4 mi Hoosic River TrailHike1.4 mi West mountain trailHike1.4 mi Shaker brook trail1.4 mi Carpenter TrailHike1.4 mi Bates BypassHike1.4 mi North TrailHike1.4 mi Baldhead spur trailHikeMTB1.4 mi Drury TrailHike1.3 mi Parker brook trail1.3 mi PortugeseHikeMTB1.3 mi Esau’s Heel TrailHike1.3 mi New Marlboro Preserve LoopHike1.3 mi Hiking Trail (Summer)Hike1.3 mi Mahanna Cobble TrailHike1.3 mi Holy mount trailHike1.3 mi Perry's Peak LoopHike1.2 mi Brickhouse Mountain Trail1.2 mi Shaker TrailHike1.2 mi Old Baldhead RoadHike1.2 mi Deer HillHike1.2 mi Tipperary Trail1.2 mi Bailey TrailHike1.2 mi Deer Hill TrailHike1.2 mi Lewis Hill TrailHike1.2 mi Ledge Trail (blue)Hike1.2 mi Ross Brook TrailHike1.1 mi Upper Jug End Loop TrailHike1.1 mi Birch Brook TrailHike1.1 mi Tenney Hill trailHike1.1 mi BumpusHike1.1 mi Flat Rock Hill TrailHike1.1 mi Brook Trail1.1 mi Trail to Balance RockHike1.1 mi Tyringham Cobble LoopHike1.1 mi Elbow TrailHike1.1 mi Savoy Kanary Kats TrailHike1.1 mi mixed woods trailHike1.1 mi Notch RoadHike1.1 mi Jones Nose TrailHike1.1 mi Diane's TrailHike1.1 mi Unmaintained Woods RoadHike1.1 mi Basin Pond Upper RouteHike1.1 mi Doll mountain trail1.1 mi Ragged mtn pathHike1.1 mi Old Mohawk TrailHike1.1 mi Ski and Bridle TrailHike1.1 mi Charcoal Pit TrailHike1.1 mi Burgoyne Pass (old road)Hike1.0 mi Rounds Rock TrailHike1.0 mi Judges HillHike1.0 mi Moser Farm Loop EastHikeMTB1.0 mi C.C.C. TrailHike1.0 mi North family trailHike1.0 mi Nordic TrailHike1.0 mi Class of '98 TrailHike1.0 mi Niles TrailHike1.0 mi Trail of the LedgesHike1.0 mi Bullock TrailHike1.0 mi Clover Trail1.0 mi Golden Hill TrailHike1.0 mi Saddle TrailHike1.0 mi Fitch TrailHike1.0 mi Vosburgh CC Trail0.9 mi Old Wildcat TrailHike0.9 mi Woodland TrailHike0.9 mi Old Benedict Pond RoadHike0.9 mi Main Outer LoopHike0.9 mi Kite Hill TrailHike0.9 mi Dave Chapin TrailHike0.9 mi Shepherds Well TrailHike0.9 mi H.H. Fitzroy TrailHike0.9 mi Campground TrailHike0.9 mi Louise Lane (North Loop)Hike0.9 mi Sacred Way TrailHike0.9 mi Bob's Ski LoopHike0.9 mi Lower Loop trailHike0.9 mi Buxton School TrailHike0.9 mi Gorge Trail (North Side)Hike0.9 mi Overbrook TrailHike0.9 mi Hickey trail (yellow)Hike0.9 mi Snowmobile TrailHikeMTB0.9 mi Quicksand TrailHike0.9 mi Burnett Pond TrailHikeMTB0.9 mi Circuit TrailHike0.9 mi Upper Po-KneeHikeMTB0.9 mi Judges NorthHike0.8 mi Upper RollercoasterHike0.8 mi Stetson TrailHike0.8 mi AspinwallHikeMTB0.8 mi Turnpike TrailHike0.8 mi Hawthorne trail0.8 mi Back RoadHikeMTB0.8 mi Judges SouthHike0.8 mi Gorge Trail (South Side)Hike0.8 mi Stevens Glen TrailHike0.8 mi Stevens Glenn Loop TrailHike0.8 mi Dunbar Brook TrailHike0.8 mi Housatonic Flats TrailHike0.8 mi Loom Brook TrailHike0.8 mi Moser Farm Loop WestHikeMTB0.8 mi Sages Ravine Campsite Trail0.8 mi Logging TrailHike0.8 mi Lara Lookout TrailHike0.8 mi Danny Boy's Trail0.8 mi Summit TrailHike0.8 mi Laurel Knob TrailHike0.8 mi Wild Acres ParkHike0.8 mi Orange TrailHike0.8 mi Hermit Thrush LoopHike0.8 mi MoonwartHikeMTB0.8 mi Sugarloaf Trail0.8 mi Trail BHikeMTB0.8 mi Hopkins-Gale TrailHike0.8 mi Sucker Brook TrailHike0.8 mi Lost Pond TrailHike0.8 mi Old Motion LoopHike0.8 mi Trail CHikeMTB0.8 mi Hemlock Brook LoopHike0.8 mi Trail I (Wild Turkey)HikeMTB0.7 mi Buxton Ravine TrailHike0.7 mi Dunbar RoadHike0.7 mi Mary Flynn TrailHike0.7 mi Caves TrailHike0.7 mi Turner Trail0.7 mi Cascades TrailHike0.7 mi Stage TrailHike0.7 mi Beaver Tail TrailHike0.7 mi Kalarama TrailHike0.7 mi Brothers TrailHike0.7 mi Fire Tower TrailHikeMTB0.7 mi Little Dragon TailHikeMTB0.7 mi Chestnut TrailHike0.7 mi Killarney Trail0.7 mi Old Thunderbolt Trail0.7 mi Sears RoadHikeMTB0.7 mi Honey BearHike0.7 mi North Branch Trail0.7 mi Guilder Pond LoopHike0.7 mi JFK Trail0.7 mi Mount Frissell TrailHike0.7 mi Mt. FrissellHike0.7 mi Tractor PathHike0.7 mi Hunter Family Loop TrailHike0.7 mi Cross Over Trail (purple)Hike0.7 mi Peeskawso Peak Trail (red)Hike0.7 mi Smith TrailHike0.7 mi Tulip Tree TrailHike0.6 mi Carriage RoadHike0.6 mi Old Mill Trail (accessible)Hike0.6 mi South Pond LoopHike0.6 mi WRLF Loop TrailHike0.6 mi Shadow ski trail0.6 mi WoolseyHikeMTB0.6 mi Orchard TrailHike0.6 mi Bog Pond TrailHike0.6 mi Hathaway TrailHike0.6 mi Mossy Bottom TrailHike0.6 mi Stone Bench TrailHike0.6 mi Oak LoopHike0.6 mi

Trails by town in Berkshire County

More Massachusetts counties

Suffolk County

121 trails · 175 mi

Worcester County

990 trails · 1,017 mi

1,339 trails · 1,542 mi

← 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 September 24, 2026.