111 Things to do near Winchester, CT
first prev 1 2 3 4 5 6 next lastShowing results within 50 miles Distance miles of Winchester, CT, USA City, Zip, or Address
Gilbert Mountain / Winsted Woods
Winchester, Connecticut
2.1 miles EA mountain bike trail with remnants of old race markings and newer connecting singletrack winding through Gilbert Mountain — expect some washout and route-finding between segments.
Mountain Bike
Satans Kingdom
New Hartford, Connecticut
9.5 miles SESwim near New Hartford, Connecticut
Swim
Hubbard River
Granville, Massachusetts
11.2 miles NESwim near Granville, Massachusetts
Swim
Buck River
Sandisfield, Massachusetts
11.8 miles NSwim near Sandisfield, Massachusetts
Swim
Mohawk Mountain State Park
Cornwall, Connecticut
12.3 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
Umpachene Falls
New Marlborough, Massachusetts
13.7 miles NWSwim near New Marlborough, Massachusetts
Swim
Carpenter's Falls
Granby, Connecticut
13.8 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
14.6 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
15.8 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
Sessions Woods
Burlington, Connecticut
16.1 miles SEA Sessions Woods trail system with a fun mix of rocks and roots, plus connections to nearby areas — road crossings included.
Mountain Bike
Thomaston Dam
Thomaston, Connecticut
16.8 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
Granville Gorge
Southwick, Massachusetts
17.5 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
Penwood State Park
Simsbury, Connecticut
18.1 miles EAn 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
Riga Falls
Salisbury, Connecticut
18.5 miles WRiga Falls is a scenic, little-known waterfall and swimming hole on Wachocastinook Creek in Connecticut's wild Mount Riga Preserve near Salisbury.
Swim
Salmon River
Salisbury, Connecticut
18.5 miles WSwim near Salisbury, Connecticut
Swim
Winding Trails
Farmington, Connecticut
18.8 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
Cowles Park
East Granby, Connecticut
18.8 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
19.1 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
Kent Falls State Park
Kent, Connecticut
19.3 miles SWA scenic waterfall park in Kent, Connecticut where the lot fills fast on summer weekends — arrive early; the park closes to new visitors once the lot reaches capacity.
Hike
Heublein Tower
West Hartford, Connecticut
19.5 miles SEA mix of singletrack, double trail, and gravel roads with beautiful views from Heublein Tower — ride counterclockwise for the best experience.
Mountain Bike
