About hiking in Berkshire County

Berkshire County, Massachusetts has 496 named trails tagged for hiking, covering 615 miles, an average of 1.2 miles each. The longest is Taconic Crest Trail, at 19.0 miles. 16 run 5 miles or longer.

What the hiking trails in Berkshire County are like

By length, 320 are under a mile, 160 run 1 to 5 miles, and 16 are 5 miles or longer. 25 are loops, ending where they start; the longest is Mother Loop Trail, at 9.5 miles.

Every one carries a difficulty rating: 194 easy, 260 moderate, and 42 hard. Of the 480 with measured elevation, South Taconic Trail climbs the most, about 7,098 ft, and 23 gain 1,000 ft or more.

Hiking Trails — page 1 of 2

Taconic Crest TrailHike19.0 mi Mahican-Mohawk Trail (M-M)Hike16.8 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 TrailHike4.4 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 Red TrailHikeMTB3.7 mi Huckleberry Trolley LineHike3.6 mi Sara Tenney TrailHike3.6 mi Northrup TrailHike3.6 mi Shaker Mountain TrailHike3.6 mi Schoolhouse LoopHike3.6 mi Roaring Brook TrailHike3.5 mi MinorHike3.4 mi Ashley Hill TrailHike3.4 mi Schemerhorn TrailHike3.4 mi Woodason Spring TrailHike3.3 mi Eagle Ledge TrailHike3.3 mi Hopper TrailHike3.3 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 HonoluluHike2.8 mi RRR Brooks trailHike2.8 mi Hammertown LoopHike2.7 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 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 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 Bernard Farm TrailHike2.1 mi Taconic Crest TrailHike2.1 mi Bob's WayHike2.0 mi Pine Cobble TrailHike2.0 mi Downtown LoopHike2.0 mi Beacon TrailHike2.0 mi Race Brook TrailHike1.9 mi Unmaintained trailHike1.9 mi Overlook TrailHike1.9 mi Laurel TrailHike1.9 mi WindsorHike1.9 mi Kamick TrailHike1.9 mi Class of 1933 TrailHike1.8 mi Spruce TrailHike1.8 mi Finerty TrailHike1.8 mi Mt. Prospect TrailHike1.8 mi Willow's Trail (orange)Hike1.8 mi Haley Farm TrailHike1.7 mi Charcoal TrailHike1.7 mi Charcol TrailHike1.7 mi Stony LedgeHike1.7 mi Stone Hill Road TrailHike1.7 mi Old Berlin Mountain Ski TrailHike1.7 mi Red Gate TrailHike1.7 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 RoadHikeMTB1.5 mi October Mountain TrailHike1.5 mi Log HopHikeMTB1.5 mi Stony Ledge Ski TrailHike1.5 mi Bear ClawHike1.5 mi Lulu Brook TrailHike1.5 mi Phelps TrailHike1.4 mi Edie's Way (South Loop)Hike1.4 mi Beebe TrailHike1.4 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 Carpenter TrailHike1.4 mi Bates BypassHike1.4 mi North TrailHike1.4 mi Baldhead spur trailHikeMTB1.3 mi Drury TrailHike1.3 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 North Family TrailHike1.2 mi Shaker TrailHike1.2 mi Old Baldhead RoadHike1.2 mi Deer HillHike1.2 mi Bailey TrailHike1.2 mi Deer Hill TrailHike1.2 mi Lewis Hill TrailHike1.2 mi Ledge Trail (blue)Hike1.2 mi Ross Brook TrailHike1.2 mi Upper Jug End Loop TrailHike1.2 mi Birch Brook TrailHike1.1 mi Tenney Hill trailHike1.1 mi BumpusHike1.1 mi Flat Rock Hill TrailHike1.1 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 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 Nordic TrailHike1.0 mi Class of '98 TrailHike1.0 mi Niles TrailHike1.0 mi Trail of the LedgesHike1.0 mi Bullock TrailHike1.0 mi Golden Hill TrailHike1.0 mi Saddle TrailHike1.0 mi Fitch TrailHike1.0 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 Circuit TrailHike0.9 mi Burnett Pond TrailHikeMTB0.9 mi Upper Po-KneeHikeMTB0.9 mi Old Woods RoadHike0.9 mi Judges NorthHike0.9 mi Upper RollercoasterHike0.9 mi Stetson TrailHike0.8 mi AspinwallHikeMTB0.8 mi Turnpike TrailHike0.8 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 Logging TrailHike0.8 mi Lara Lookout TrailHike0.8 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 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 LoopHike0.7 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 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 Sears RoadHikeMTB0.7 mi Honey BearHike0.7 mi Guilder Pond LoopHike0.7 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 TrailHike0.6 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 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 Deborah Reich TrailHike0.6 mi Hal Borland TrailHike0.6 mi Ursula Cliff TrailHike0.6 mi Hemlock HollowHikeMTB0.6 mi Trail DHikeMTB0.6 mi Lime Kiln LoopHike0.6 mi Trail H (Jericho)Hike0.6 mi The Nature Conservancy AT Connector TrailHike0.6 mi South Side ConnectorHikeMTB0.6 mi Secret TrailHike0.5 mi Becket Historic Quarry and Forest TrailHike0.5 mi Ten-Point BuckHike0.5 mi Wolf Pine TrailHike0.5 mi Meeting House Loop TrailHike0.5 mi Carl Reidel TrailHikeMTB0.5 mi Grashopper LoopHikeMTB0.5 mi Bentely Hollow trailHike0.5 mi Garnet Hill TrailHike0.5 mi The CirqueHikeMTB0.5 mi Ledges TrailHike0.5 mi March Cataract TrailHike0.5 mi Covered Bridge LaneHike0.5 mi Basin Pond Lower RouteHike0.5 mi Founders LoopHike0.5 mi Brookside TrailHike0.5 mi bumps trailHike0.5 mi Haskins TrailHikeMTB0.5 mi Johnny MashHike0.5 mi Vermont Line TrailHike0.5 mi

← All Berkshire County trails

Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt October 25, 2026.