About trails in Cheshire County, New Hampshire

Cheshire County has 221 named trails on the map, covering 448 miles in total, an average of 2.0 miles per trail. That is the 8th largest mapped trail network among 10 counties in New Hampshire. 212 of them are tagged for hiking and 15 for mountain biking.

The longest single trail is Wantastiquet-Monadnock Trail, at 45.0 miles. 12 trails run 5 miles or longer. Mapped points of interest in the county include 5 trailheads, 18 campsites, 18 waterfalls, 16 boat launches, and 1 rapid. The nearest towns to these trails are Jaffrey, Hinsdale, and Troy.

What the trails in Cheshire County are like

By length, 128 are under a mile, 81 run 1 to 5 miles, and 12 are 5 miles or longer. 36 are loops, ending where they start; the longest is Pumpelly Trail, at 7.8 miles.

Of the 221 with measured elevation, Monadnock-Sunapee Greenway climbs the most, about 8,715 ft, and 16 gain 1,000 ft or more.

Explore by activity

448Total miles

18Campsites

16Boat launches

18Waterfalls

5Trailheads

1Rapids

Wantastiquet-Monadnock TrailHike45.0 mi Cheshire Recreational Rail TrailMTB39.2 mi Monadnock-Sunapee GreenwayHike26.3 mi Monadnock Recreational Rail TrailHikeMTB21.7 mi Ashuelot Recreational TrailMTB21.5 mi Ashuelot Rail TrailHikeMTB21.4 mi Cheshire Rail TrailHikeMTB8.4 mi Pumpelly TrailHike7.8 mi Reservoir TrailHike7.2 mi Fort Hill Recreational TrailMTB6.6 mi Kilburn LoopHike5.5 mi Cascade LinkHike5.2 mi Wantastiquet Mountain TrailHike4.7 mi White Cross TrailHike4.7 mi Monadnock Sunapee GreenwayHike4.6 mi Monadnock Sunapee Greenway TrailHike4.5 mi Metacomet- Monadnock TrailHike4.4 mi Royce TrailHike4.4 mi Hinkley TrailHike4.3 mi Anne Stokes Loop TrailHike4.0 mi Lost Farm TrailHike3.9 mi Marlboro TrailHike3.8 mi Parker TrailHike3.8 mi Metacomet-Monadnock TrailHike3.6 mi Birchtoft TrailHike3.6 mi White Dot TrailHike3.5 mi Daniels Mountain LoopHike3.3 mi Fullam Pond TrailHike3.1 mi Dogwood Swamp TrailHike3.0 mi Wantastiquet-Monadnock Trail (Prouty Road -Chesterfield Rd)Hike3.0 mi Reservoir RoadHike2.9 mi Pisgah Ridge TrailHike2.9 mi Broad Brook RoadHike2.8 mi Harling TrailHike2.8 mi Cliff WalkHike2.7 mi Pond LoopHike2.7 mi Hinsdale Snowmobile Trail (approx location)Hike2.6 mi Old Halfway House TrailHike2.4 mi Metacomet Monadnock Trail (White)Hike2.3 mi Blue TrailHike2.3 mi Old Richmond RoadHike2.2 mi Old Chesterfield RoadHike2.2 mi Dublin TraiHike2.1 mi Underwood RoadHike2.1 mi Marian TrailHike2.1 mi Center Pond RoadHike2.1 mi Chestnut Hill TrailHike2.0 mi Monadnock-Sunapee TrailHike1.9 mi Dublin Trail / Monadnock-Sunapee GreenwayHike1.9 mi Gilson Pond Remote Campsites LoopHike1.9 mi White Arrow TrailHike1.9 mi The Outer LoopHike1.9 mi Harrisville Rail TrailHike1.8 mi Converse PathHike1.8 mi South Woods Tr.Hike1.7 mi Yellow BlazesHike1.7 mi Red Spot TrailHike1.7 mi Yellow RectangleHike1.7 mi Snowbrook TrailHike1.7 mi Holt Trail (blue)Hike1.6 mi Ridgeline TrailHike1.6 mi Davis Hill TrailHike1.6 mi Bear Mountain TrailHike1.5 mi Hubbard Hill TrailHike1.5 mi Kulish Ledges Trail (yellow)Hike1.5 mi Amphitheatre TrailHike1.5 mi Mine Ledge TrailHike1.4 mi Daniels Mountain TrailHike1.4 mi Horatio Colony Preserve Red Diamond TrailHike1.4 mi Red DiamondHike1.4 mi Bates King TrailHike1.4 mi Hello RockHike1.4 mi Eastview TrailHike1.3 mi West Ridge TrailHike1.3 mi Wantastiquet-Monadnock Trail (Ridgeline Trail to Forest Ave)Hike1.3 mi Ribbon CandyHike1.3 mi Sapporo (Blue)Hike1.3 mi Smith Summit TrailHike1.3 mi Bowker RoadHikeMTB1.2 mi Great Pasture TrailHike1.2 mi Ridge Trail (Orange)Hike1.2 mi Baker Pond TrailHike1.2 mi Appel WayHike1.2 mi John Hill RoadHike1.2 mi Little Monadnock TrailHike1.1 mi Smith ConnectingHike1.1 mi Town Forest TrailHike1.1 mi PerimeterHike1.1 mi Side Foot TrailHike1.1 mi North Ponds TrailHike1.1 mi Elisabeth B. McIntire TrailHike1.0 mi Lily Pond TrailHike1.0 mi Bike LoopHike1.0 mi Doolittle TrailHike1.0 mi Tippin Rock TrailHike0.9 mi Red ArrowHike0.9 mi Gardiner Mountain trailHike0.9 mi Table Rock Trail0.9 mi Blue trail (Widow Gage)Hike0.9 mi Caleb's WayHike0.9 mi Gage TrailHike0.9 mi Tower Trail (red)Hike0.9 mi Spellman TrailHike0.9 mi Cart PathHike0.9 mi Point Surprise TrailHike0.9 mi Ms Mt Pitcher TrailHike0.9 mi CliffsideHike0.8 mi Green PineHike0.8 mi Dublin Rotary TrailHike0.8 mi JumpHikeMTB0.8 mi Wild ThingsHike0.8 mi Gramwick TrailHike0.8 mi Jaquith Rail TrailHike0.8 mi Do Drop TrailHike0.8 mi Blue dotHike0.8 mi Blue HeronHike0.8 mi Tetreault TrailHike0.7 mi Zophar Willard TrailHike0.7 mi Monte RosaHike0.7 mi Red RectangleHike0.7 mi Wheeler Trail (yelllow)0.7 mi Red Mill RoadHike0.7 mi Carroll's Hill PathHike0.6 mi Dodge Farm RoadHike0.6 mi Lake Placid Loop (Green)0.6 mi Beech Hill TrailHike0.6 mi Nash trailHike0.6 mi Horseshoe RoadHikeMTB0.6 mi Tom Duston TrailHike0.6 mi Thoreau TrailHike0.6 mi Bailey Brook Trail (yellow)Hike0.6 mi Elijah's Epic Summit Trail (yellow)Hike0.6 mi Cold River TrailHike0.6 mi Rope TowHikeMTB0.6 mi Old Davis Hill TrailHike0.6 mi Fairy SpringHike0.6 mi Spur Trail to Western CoveHike0.6 mi Orchard TrailHike0.6 mi Red trail (Widow Gage)Hike0.6 mi Mossy Brook TrailHike0.5 mi Beal's Knob TrailHike0.5 mi South LinkHike0.5 mi Ravine TrailHike0.5 mi Gorge TrailHike0.5 mi Loop A0.5 mi Preferred RouteHike0.5 mi Logger pathHike0.5 mi TownlineHike0.5 mi Hurd Hill Trail (Yellow)Hike0.5 mi River TrailHike0.5 mi Rhododendron Loop TrailHike0.4 mi Lorna's TrailHike0.4 mi Sands TrailHike0.4 mi ButterHike0.4 mi Abandoned Railroad GradeHike0.4 mi Noble TrailHike0.4 mi Sunset Rocks trailHike0.3 mi Habitat Tr.Hike0.3 mi Warm Up Trail (Yellow)0.3 mi Kamikaze SlalomHikeMTB0.3 mi TabootHike0.3 mi Beginner Bike LoopHike0.3 mi Kulish Ledge Trail (yellow)Hike0.3 mi Green SquareHike0.3 mi Osgood Hill Link TrailHike0.3 mi Donovan TrailHike0.3 mi Loop B0.3 mi South Gap MountianHike0.3 mi Red TrailHike0.3 mi Rock River TrailHike0.3 mi Stony FieldHike0.3 mi Crider Forest Shelter TrailHike0.3 mi Yellow TrailHike0.3 mi Nye RoadHike0.3 mi Green DiamondHike0.2 mi Not a Maintained TrailHike0.2 mi Winchester RoadHikeMTB0.2 mi Clay CornersHike0.2 mi Warning TrackHike0.2 mi Black Lead Mine TrailHike0.2 mi Robin Hood TrailHike0.2 mi Red SquareHike0.2 mi Yellow BypassHike0.2 mi South Woods Side-Tr.Hike0.2 mi Wood boundHike0.2 mi North Round Pond TrailHike0.2 mi Old Ski PathHike0.2 mi Red dotHike0.2 mi Reservoir Street TrailHikeMTB0.2 mi Orange DotHike0.2 mi Yellow SunsetHike0.2 mi Dort Shelter-Hubbard Hill Vista ConnectorHike0.2 mi Sip Pond Peninsula TrailHike0.2 mi Davis Hill-Dort Shelter ConnectorHike0.2 mi Wildflower TrailHike0.2 mi Dublin Trail // Monadnock-Sunapee GreenwayHike0.2 mi Lewis Pond RoadHikeMTB0.2 mi Rocky TopHike0.2 mi Blarney stone RoadHike0.2 mi Dublin Rotary Canoe TrailHike0.2 mi MooseHike0.2 mi Green On WhiteHike0.2 mi FlickerHike0.2 mi Bennett GorgeHike0.2 mi Beginner Bike PathHike0.2 mi Sandy Beach PathHike0.2 mi Dort Knob Vista TrailHike0.2 mi Dog WalkHike0.1 mi Old Norse RoadHikeMTB0.1 mi Fox Brook Tent Site TrailHike0.1 mi Beal's Knob Summit Spur TrailHike0.1 mi Private StockHike0.1 mi Hubbard Hill Vista LoopHike0.1 mi Priscilla TrailHike0.1 mi Old Quarry RoadHike0.1 mi SacrificeHike0.1 mi SocialHike0.1 mi Converse Path Camping AreaHike0.1 mi Portage PathHike0.1 mi Yellow DotHike0.1 mi Laurel TrailHike0.1 mi

Trails by town in Cheshire County

More New Hampshire counties

531 trails · 1,375 mi

Grafton County

813 trails · 1,333 mi

← All of New Hampshire

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.