About hiking in Hampshire County

Hampshire County, Massachusetts has 336 named trails tagged for hiking, covering 287 miles, an average of 0.9 miles each. The longest is Robert Frost Trail, at 25.2 miles. 5 run 5 miles or longer.

What the hiking trails in Hampshire County are like

By length, 269 are under a mile, 62 run 1 to 5 miles, and 5 are 5 miles or longer. 6 are loops, ending where they start; the longest is Roxanne's Trail - G-Ma's Loop, at 1.0 mile.

Of the 148 with a difficulty rating, 44 easy, 67 moderate, and 37 hard. Of the 335 with measured elevation, Robert Frost Trail climbs the most, about 6,655 ft, and 4 gain 1,000 ft or more.

Hiking Trails — page 1 of 2

Robert Frost TrailHike25.2 mi Robert Frost Trail (Orange)HikeMTB10.3 mi Norwottuck Rail TrailHikeMTB10.2 mi NET/M&M Trail (white)HikeMTB10.0 mi Ken Cuddeback TrailHike6.6 mi NET/M&M/RFT Trail (white/blue/orange)HikeMTB3.8 mi NET Trail (white)HikeMTB3.7 mi Lithia Springs TrailHikeMTB3.5 mi Phased and ConfusedHike3.5 mi Belchertown GreenwayHikeMTB3.1 mi broad brook loopHike2.6 mi Norwottuck Rail Trail (Francis P. Ryan Section)HikeMTB2.6 mi Factory Brook Loop TrailHike1.9 mi Salamander Loop TrailHikeMTB1.9 mi Glenna BellHikeMTB1.8 mi The Wedge/Ridge LineHikeMTB1.7 mi Old Fire Road TrailHike1.7 mi North SideHikeMTB1.7 mi Francis P. Ryan Section of the Norwottuck Rail TrailHikeMTB1.7 mi Long TrailHike1.7 mi Keystone Arch Bridges TrailHike1.7 mi Cold Spring RoadHike1.6 mi Red LoopHike1.6 mi River to Range TrailHike1.5 mi Visitor's Center Loop TrailHike1.5 mi RaybunctiousHikeMTB1.5 mi Blood Donor / Night OwlHike1.5 mi Fuller Brook TrailHike1.5 mi Jeep EaterHike1.5 mi Lyman Brook LoopHike1.4 mi West Farm RoadHikeMTB1.4 mi Observation Tower TrailHike1.4 mi Noah Webster TrailHike1.4 mi (overgrown)Hike1.4 mi Maze RoadHikeMTB1.4 mi Dry Brook TrailHike1.4 mi Pontoosuc TurnpikeHike1.4 mi Middle Access RoadHikeMTB1.4 mi Upper AccessHikeMTB1.3 mi Enfield Lookout TrailHike1.3 mi Roller CoasterHikeMTB1.3 mi Middle PathHike1.3 mi For the AnimalsHikeMTB1.3 mi Whsipering Winds LoopHike1.3 mi Parsons Swamp RoadHike1.2 mi Far SideHikeMTB1.2 mi DCR GrantHike1.2 mi Bobcat TrailHike1.2 mi Wild SideHike1.2 mi Lower AccessHikeMTB1.2 mi yellow blazesHikeMTB1.2 mi East Farm RoadHikeMTB1.2 mi NEMBA TrailHike1.2 mi Massachusetts Central Rail TrailHikeMTB1.1 mi Missing PersonsHikeMTB1.1 mi Far OutHikeMTB1.1 mi Southern BelleHikeMTB1.1 mi Central Massachusetts BranchHike1.1 mi Old Carriage TrailHike1.1 mi Blue Blazed Loop TrailHike1.1 mi SpatulaHikeMTB1.1 mi Old trailHike1.1 mi Northern Trail ExtensionHike1.1 mi Sand Trap/DriverHikeMTB1.1 mi Amherst College XC CourseHike1.1 mi Sugarbush TrailHike1.0 mi Flat RockHikeMTB1.0 mi Tessman LoopHikeMTB1.0 mi Fort River Birding and Nature TrailHike1.0 mi Roxanne's Trail - G-Ma's LoopHike1.0 mi Ken Cuddeback Trail (Blue)Hike1.0 mi John W. Oliver TrailHike1.0 mi Horse Mountain trailHike1.0 mi Main Trail (orange rectangle blaze)Hike1.0 mi Swift WayHikeMTB1.0 mi Sliced ItHike1.0 mi Red Barn RoadHikeMTB1.0 mi Notch LinkHikeMTB0.9 mi TwisterHikeMTB0.9 mi UFOHike0.9 mi Rivulet TrailHike0.9 mi Trolley BedHikeMTB0.9 mi Ghost TrainHikeMTB0.9 mi Swiss MissHikeMTB0.9 mi Pinnacle TrailHike0.9 mi M&M Trail (Old Route)Hike0.9 mi Jeffrey R. Wood Farm TrailHike0.9 mi Dickinson TrailHike0.9 mi Katherine Cole TrailHike0.9 mi Condo SingletrackHikeMTB0.9 mi Jacob's LadderHikeMTB0.9 mi Halfway House Trail (Blue)Hike0.9 mi Trolley Bed TrailHikeMTB0.8 mi Old Post RoadHike0.8 mi Bunker HillHike0.8 mi Fitzgerald's FolliesHikeMTB0.8 mi Tinker TrailHikeMTB0.8 mi Far EastHikeMTB0.8 mi Old Trolley Line trailHike0.8 mi Petticoat Hill/Locke's LoopHike0.8 mi Black Bear TrailHike0.8 mi Ellsworth Barnard LoopHike0.8 mi Pete’s WickedHikeMTB0.8 mi MomsHike0.8 mi Upper TrailHike0.7 mi Red TrailHike0.7 mi Summit TrailHike0.7 mi Historic Dam TrailHike0.7 mi Robert's Meadow Brook Trail (red)Hike0.7 mi Porter-Phelps-Huntington Museum Farm LoopHike0.7 mi IMBA AccessHikeMTB0.7 mi The Blue TrailHikeMTB0.7 mi Link RoadHikeMTB0.7 mi Amherst ConservationHikeMTB0.7 mi RFT (orange)HikeMTB0.7 mi Northampton BikewayHikeMTB0.7 mi Christmas TrailHikeMTB0.7 mi DingleberryHikeMTB0.7 mi Central LoopHike0.7 mi SerpentineHikeMTB0.7 mi Lithia Springs RoadHikeMTB0.7 mi Tinker ToyHikeMTB0.7 mi Out of BoundsHike0.7 mi Devil's FootballHike0.7 mi The White TrailHikeMTB0.7 mi Graves Brothers Loop TrailHike0.7 mi blue blazesHike0.7 mi Mount Pollux TrailHikeMTB0.7 mi Mt. Warner ConnectorHike0.7 mi Marian Street Trail (blue)HikeMTB0.7 mi Leaping Well Nature TrailHike0.7 mi Jan Dizard Trail (Red)Hike0.7 mi Lithia BypassHike0.7 mi Thermopylae AccessHikeMTB0.7 mi Serpent GodHikeMTB0.7 mi Tilton Farm TrailHike0.7 mi Julius Lester TrailHike0.7 mi Pond TrailHikeMTB0.7 mi Falling BridgeHikeMTB0.6 mi Harkness Brook Trail (Yellow)Hike0.6 mi Blue Triangle TrailHike0.6 mi Maze Road (alt)HikeMTB0.6 mi Long Mountain RoadHikeMTB0.6 mi Darling TrailHike0.6 mi Taylor's Notch Trail/RFT (Yellow/Orange)Hike0.6 mi Backend TrailHike0.6 mi Triple B/RFT (orange)HikeMTB0.6 mi Brook TrailHike0.6 mi red blazesHike0.6 mi JFK LoopHike0.6 mi Hillside Trail (red)HikeMTB0.6 mi Conglomerate RockHike0.6 mi Boy Scout TrailHike0.6 mi Lowland LoopHikeMTB0.6 mi Down DeepHikeMTB0.6 mi Oogamak TrailHike0.6 mi Swamp Forest TrailHike0.6 mi Lithia Outlook Trail/RFT (orange)Hike0.6 mi Private InvestigationHikeMTB0.6 mi Fort River TrailHike0.6 mi Holland Glen EastHike0.6 mi Wolf Hill SanctuaryHike0.5 mi White Pine TrailHike0.5 mi Beary's TrailHike0.5 mi Mt. HitchcockHike0.5 mi Notch BypassHike0.5 mi Truckin'Hike0.5 mi Town TrailHike0.5 mi BrookbankHike0.5 mi Lake Trail (blue)HikeMTB0.5 mi Unsolved MysteryHikeMTB0.5 mi 40 Foot TrailHike0.5 mi Ice Pond LoopHike0.5 mi Brookside TrailHike0.5 mi Black Rock TrailHike0.5 mi No Man's LandHikeMTB0.5 mi orange blazesHike0.5 mi Nancy Weiss TrailHike0.5 mi Bunker Link/RFT (orange)HikeMTB0.5 mi East TrailHike0.5 mi Swamp Trail (Red)Hike0.5 mi Dorie Goldman Trail (light blue)Hike0.5 mi RaptorHikeMTB0.5 mi Em’s GemHikeMTB0.5 mi Lizard KingHikeMTB0.5 mi Turkey Hill RoadHike0.5 mi Technical TrailHikeMTB0.5 mi Hunter TrailHikeMTB0.5 mi Big Tree TrailHikeMTB0.5 mi Holland GlenHike0.5 mi Other Swamp TrailHikeMTB0.5 mi Green Loop TrailHike0.5 mi Two ForestHike0.5 mi Upper Donkey PunchHikeMTB0.5 mi Huckleberry’s WayHike0.5 mi Groundward DownHikeMTB0.5 mi Double BogeyHikeMTB0.5 mi Twistin' TristanHikeMTB0.4 mi Pond Loop TrailHike0.4 mi Alice Brown TrailHike0.4 mi Lovefield Division TrailHike0.4 mi Better AccessHikeMTB0.4 mi DoghouseHikeMTB0.4 mi Lost & FoundHikeMTB0.4 mi Poverty Ridge RunHikeMTB0.4 mi White Rock North RouteHike0.4 mi Pink FlamingoHike0.4 mi Sunset TrailHike0.4 mi TramwayHike0.4 mi Middle EarthHikeMTB0.4 mi Old Stage RoadHike0.4 mi Overlook TrailHike0.4 mi Entrance ExamHikeMTB0.4 mi Lithia Springs Trail/RFT (orange)HikeMTB0.4 mi Turkey TrailHike0.4 mi ViperHikeMTB0.4 mi Two Deer TrailHikeMTB0.4 mi Mt Tom North Accessible TrailHike0.4 mi Wall StreetHikeMTB0.4 mi Beaver Brook Conservation AreaHike0.4 mi Hollow RoadHikeMTB0.4 mi Habitat TrailHike0.4 mi T-RexHikeMTB0.4 mi Knee BreakerHikeMTB0.4 mi Junkyard DogHike0.4 mi Old Telephone Line TrailHikeMTB0.4 mi Laurel LoopHike0.4 mi Old Telephone LineHike0.4 mi Jump TrailHike0.4 mi Terrace Trails (Red Trail)Hike0.4 mi Bunker LinkHikeMTB0.4 mi MulliganHike0.4 mi Well-Away Farm TrailHike0.4 mi Timber Frame Inner LoopHike0.4 mi Caroline Arnold Trail (Yellow)Hike0.4 mi Tricky Turn TrailHikeMTB0.4 mi Quarry LoopHike0.4 mi Margin CallHikeMTB0.4 mi Robert LaPlam TrailHike0.3 mi Ravine TrailHike0.3 mi Ray Stannard Baker TrailHike0.3 mi Sweet Alice TrailHike0.3 mi Low Place TrailHikeMTB0.3 mi Childs Park Road CHikeMTB0.3 mi Low Place Trail/RFT (orange)HikeMTB0.3 mi Southside Trail (Blue)Hike0.3 mi Nedobak TrailHike0.3 mi Childs Park Road BHikeMTB0.3 mi Holland Glen WestHike0.3 mi Tulip Tree TrailHike0.3 mi Crankie CaddieHike0.3 mi Pine Brook Trail (yellow)Hike0.3 mi Pine LoopHike0.3 mi Orchard Hill to Sylvan FootpathHike0.3 mi Tire TesterHike0.3 mi Main AccessHikeMTB0.3 mi Three AmigosHike0.3 mi Yellow Brick RoadHikeMTB0.3 mi Low DownHikeMTB0.3 mi Black Rock Trail/RFT (orange)Hike0.3 mi Romer RoadHikeMTB0.3 mi Green Square TrailHike0.3 mi Lower Tricky Turn TrailHikeMTB0.3 mi Fishing Place (white)Hike0.3 mi Bubba BrosnanHikeMTB0.3 mi Bragg Hill RoadHikeMTB0.3 mi Norwottuck Rail Trail BridgeHikeMTB0.3 mi Border Trail (green/teal rectangle blaze)Hike0.3 mi Little Mountain Loop TrailHike0.3 mi SporkHikeMTB0.3 mi PeriwinkleHike0.3 mi green blazesHike0.3 mi Beaver Pond LoopHike0.3 mi H. H. Jackson TrailHike0.3 mi Red Loop TrailHike0.3 mi Ellis WayHike0.3 mi Childs Park Road AHikeMTB0.3 mi Sweet AliceHike0.3 mi Potash TrailHike0.3 mi (Yellow)HikeMTB0.3 mi Nonnie Day Brook LoopHike0.2 mi Kohl TrailHike0.2 mi West TrailHike0.2 mi white blazesHike0.2 mi Tree HuggerHikeMTB0.2 mi Ladyslipper Trail (blue rectangle blaze)Hike0.2 mi Mazie LaneHike0.2 mi Lower Donkey PunchHikeMTB0.2 mi K&N Trail (orange triangle blaze)Hike0.2 mi Chaz' WickedHike0.2 mi Brookside PathHike0.2 mi Halfway Brook TrailHike0.2 mi Markert's Pond TrailHike0.2 mi Midde TrailHike0.2 mi Seelye DriveHike0.2 mi Mt. Castor Loop TrailHike0.2 mi Fox RunHike0.2 mi Yellow blazeHike0.2 mi Mt. Warner Connector Overlook LoopHike0.2 mi White Blazed TrailHike0.2 mi

← All Hampshire 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 September 27, 2026.