61 Mountain Bike Trails near Cheshire, CT
first prev 1 2 3 4 next lastShowing Mountain Bike Trails within 50 miles Distance miles of Cheshire, CT, USA City, Zip, or Address
Cheshire Lock 12
Cheshire, Connecticut
2.4 miles SA paved hiking, running, and biking path in Cheshire with a small unpaved shoulder — a smooth, accessible multi-use trail for all paces.
Mountain Bike
Brooksvale Park And Naugatuck State Forest
Hamden, Connecticut
3.8 miles SA gateway trail system near Hamden that's great for beginners and opens into the Naugatuck State Forest's awesome singletrack, serious climbs, and plenty of stunts.
Mountain Bike
Tyler Mills
Wallingford, Connecticut
8.6 miles SEA well-marked network of mostly singletrack trails in Wallingford with small loops, a nice mix of climbs and descents — ideal for intermediates building skills and flow.
Mountain Bike
Farmington Canal Heritage Trail
Hamden, Connecticut
9.0 miles SA smooth, family-friendly rail trail perfect for an easy ride together through Hamden.
Mountain Bike
West Rocks State Park
Hamden, Connecticut
10.6 miles SColor-coded trails in West Rock Park range from a grueling Yellow climb to a flat Red cruise, a White loop around Lake Wintergreen, and a tough Blue that rewards you with direct downtown New Haven views.
Mountain Bike
Middlebury Greenway
Middlebury, Connecticut
11.7 miles WA picturesque walking and biking trail converted from an old trolley bed, rolling through Middlebury with great climbs that singlespeeders especially love.
Mountain Bike
Wadsworth State Park
Middletown, Connecticut
11.8 miles EA hidden singletrack treasure in Middletown between New Haven and Hartford — interesting new singletrack, dual track, and technical sections that pop up unexpectedly at Wadsworth State Park.
Mountain Bike
Larkin State Bridal Trail
Southbury, Connecticut
13.3 miles WA multi-use trail shared by hikers, mountain bikers, cross-country skiers, and equestrians — a popular horseback riding route, so watch your step on the trail.
Mountain Bike
Rockland Preserve
Madison, Connecticut
14.6 miles SEFlowy XC singletrack with berms, log rides, jumps, and volunteer-built features at Rockland Preserve in Madison, Connecticut — including a pump track, a see-saw, and a multi-jump flow line.
Mountain Bike
Thomaston Dam
Thomaston, Connecticut
15.1 miles NWA multi-use area near Thomaston Dam with excellent valley views from the Vista picnic area, fishing along the Naugatuck River, hunting, trailbike and snowmobile riding, and a public model aircraft field.
Mountain Bike
Supply Ponds
Branford, Connecticut
15.4 miles SSteep hills, rocks, and at least one known fallen tree across the trail — a short but physical mountain bike ride that keeps you alert.
Mountain Bike
Genesee Recreation Area
Madison, Connecticut
15.4 miles SEA lightly trafficked mix of access roads and trails on water company land in Madison, Connecticut — good terrain variety and hills for a solid workout.
Mountain Bike
Sessions Woods
Burlington, Connecticut
15.7 miles NA Sessions Woods trail system with a fun mix of rocks and roots, plus connections to nearby areas — road crossings included.
Mountain Bike
Timberlands
Guilford, Connecticut
15.9 miles SEA network of singletrack and forest trails in Guilford — decent variety, though riders report it gets repetitive after a few visits.
Mountain Bike
Middlesex Community College
Middletown, Connecticut
16.0 miles EA sprawling network of singletrack, powerlines, and even a retired motocross track — every skill level welcome, though it's easy to end up 10 miles south if you lose your bearings.
Mountain Bike
Cromwell Creek
Cromwell, Connecticut
16.1 miles NESome good singletrack nuggets remain among the Cromwell Creek trails, though ATV damage has taken a toll — a modest ride worth a visit for local riders.
Mountain Bike
Lower Paugussett State Forest
Newtown, Connecticut
16.5 miles SWA 6.5-mile loop of extremely technical singletrack in Newtown with forest road connectors — ATV and MX riders also frequent the gas line sections nearby.
Mountain Bike
Winding Trails
Farmington, Connecticut
16.9 miles NA 5-mile trail complex with a fast, smooth ride and low technical challenge — home to the annual Fat Tire Classic race each April.
Mountain Bike
Nassahegan State Forest
Burlington, Connecticut
17.6 miles NA good network of trails in Nassahegan State Forest with a main loop, side trails, and a large outer loop — parking available across from the trailhead in Burlington, CT.
Mountain Bike
Stony Creek Quarry Preserve
Branford, Connecticut
18.3 miles SEA network of trails at Stony Creek Quarry Preserve in Branford, primarily marked with painted or reflective colored blazes — a solid mountain biking destination in Connecticut.
Mountain Bike
