57 Mountain Bike Trails near Gilbert Mountain / Winsted Woods
first prev 1 2 3 next lastShowing Mountain Bike Trails within 50 miles Distance miles of 180 Williams Ave, Winsted, CT 06098, USA City, Zip, or Address
Carpenter's Falls
Granby, Connecticut
11.7 miles ERough dirt road and rooty singletrack near Granby with a waterfall tucked off to the left about half a mile in — a rewarding find for riders who explore.
Mountain Bike
Nassahegan State Forest
Burlington, Connecticut
13.2 miles SEA 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
Central
Simsbury, Connecticut
13.6 miles EA constantly changing trail in Simsbury with one huge drop, plenty of jumps, and a lively crowd — great for riders who want airtime and variety.
Mountain Bike
Mohawk Mountain State Park
Cornwall, Connecticut
13.9 miles SWA 15-mile backcountry route of logging roads and singletrack climbing to the top of Mohawk Mountain, with trail junctions, river sections, and cross-country ski terrain.
Cross-country Ski, Hike, Mountain Bike
Sessions Woods
Burlington, Connecticut
14.9 miles SEA Sessions Woods trail system with a fun mix of rocks and roots, plus connections to nearby areas — road crossings included.
Mountain Bike
Penwood State Park
Simsbury, Connecticut
16.0 miles SEAn epic ridgeline trail system at Penwood State Park with single track inches from 200-foot cliffs, sweeping Farmington River Valley views, and links to trails north and south.
Mountain Bike
Granville Gorge
Southwick, Massachusetts
16.0 miles NEGranville Gorge is a magical little slice of the southern Berkshire Hills — a lush, green gorge where the Hubbard River carves a series of mini waterfalls and clear swimming holes through the...
Mountain Bike, Swim
Thomaston Dam
Thomaston, Connecticut
16.3 miles SA 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
Cowles Park
East Granby, Connecticut
16.7 miles EWell-maintained trails with a great variety of descents, climbs, flat technical sections, and fire roads — a fun, wide-ranging trail system in East Granby worth returning to.
Mountain Bike
Metacomet Trail
East Granby, Connecticut
17.0 miles EA 62.7-mile Blue-Blazed trail along Connecticut's Metacomet Ridge — part of the New England National Scenic Trail — open to hikers, backpackers, bikers, horseback riders, and in winter, snowshoers.
Hike, Mountain Bike
Winding Trails
Farmington, Connecticut
17.1 miles SEA 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
Heublein Tower
West Hartford, Connecticut
17.6 miles SEA mix of singletrack, double trail, and gravel roads with beautiful views from Heublein Tower — ride counterclockwise for the best experience.
Mountain Bike
Provin Mountain
Southwick, Massachusetts
21.6 miles NEA moderate climb with fun descents and great views — a well-rounded mountain bike ride at Provin Mountain in western Massachusetts.
Mountain Bike
Robinson state park
Agawam, Massachusetts
22.8 miles NEA fun two-hour MTB network with trails ranging from technical singletrack to fast smooth descents — watch for unmarked trails that drop off cliffs near Robinson State Park.
Mountain Bike
Windsor Locks Canal Trail
Suffield, Connecticut
24.2 miles EA 4.5-mile towpath trail along a 170-year-old historic canal with scenic vistas of both the Connecticut River and the old waterway itself.
Hike, Mountain Bike
Steep Rock
Washington, Connecticut
27.4 miles SWA fun mix of 4x4 singletrack, forest trail, and powerline downhills winding from Judd's Bridge to Steep Rock's pinnacle, with great views and a rough but exciting descent.
Hike, Mountain Bike
Middlebury Greenway
Middlebury, Connecticut
28.5 miles SA picturesque walking and biking trail converted from an old trolley bed, rolling through Middlebury with great climbs that singlespeeders especially love.
Mountain Bike
Cromwell Creek
Cromwell, Connecticut
31.2 miles SESome 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
Cheshire Lock 12
Cheshire, Connecticut
32.3 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
Larkin State Bridal Trail
Southbury, Connecticut
32.3 miles SA 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
