114 Things to do near Middlebury, CT
first prev 1 2 3 4 5 6 next lastShowing results within 50 miles Distance miles of Middlebury, CT, USA City, Zip, or Address
Middlebury Greenway
Middlebury, Connecticut
0.7 miles SWA picturesque walking and biking trail converted from an old trolley bed, rolling through Middlebury with great climbs that singlespeeders especially love.
Mountain Bike
Larkin State Bridal Trail
Southbury, Connecticut
4.5 miles SWA 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
Hotchkissville Bridge
Woodbury, Connecticut
5.4 miles NWSwim near Woodbury, Connecticut
Swim
George C. Waldo State Park
Southbury, Connecticut
9.3 miles SWA family-friendly trail in Southbury with ramps kids will love, leashed-dog access, and a well-marked red trail through the trees.
Mountain Bike
Lower Paugussett State Forest
Newtown, Connecticut
9.5 miles SA 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
Cheshire Lock 12
Cheshire, Connecticut
11.2 miles EA paved hiking, running, and biking path in Cheshire with a small unpaved shoulder — a smooth, accessible multi-use trail for all paces.
Mountain Bike
Upper Paugussett State Forest
Newtown, Connecticut
11.3 miles SWTechnical mountain biking along the water at Upper Paugussett State Forest near Newtown, with the legendary Kissing Oaks as a midpoint landmark and unmarked trails to explore throughout.
Mountain Bike
Panthorn Park
Southington, Connecticut
11.3 miles EA technical but fair wooded layout with a nice balanced mix of holes on fairly level terrain in Southington.
Disc Golf
Funny Farm North
Newtown, Connecticut
11.9 miles SWA fun singletrack loop in Newtown between railroad tracks and the river — linking the Bone Yard Trail and Newtown Trailway through green-blazed woods.
Mountain Bike
Brooksvale Park And Naugatuck State Forest
Hamden, Connecticut
11.9 miles SEA 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
Steep Rock
Washington, Connecticut
12.0 miles WA 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
Thomaston Dam
Thomaston, Connecticut
12.0 miles NA 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
Dingle Brook Trail
Brookfield, Connecticut
12.5 miles WTechnical mountain biking on old ATV and equestrian trails through Dingle Brook in Brookfield — a good workout on unmarked forest paths.
Mountain Bike
Sunny Valley
Bridgewater, Connecticut
12.5 miles WA network of trails offering serious climbs and very technical singletrack — a destination for riders who want to push their skills.
Mountain Bike
Monroe Rail Trail
Monroe, Connecticut
14.1 miles SWA family-friendly rail trail in Monroe, Connecticut with some singletrack branches — easy and enjoyable for all skill levels.
Mountain Bike
Gurski Farm
Brookfield, Connecticut
14.2 miles WDouble track and singletrack trails through pricker-bush-lined paths — a quick, easy ride great for introducing kids to trail riding.
Mountain Bike
West Rocks State Park
Hamden, Connecticut
14.3 miles SEColor-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
Page Park
Bristol, Connecticut
14.7 miles NEA mostly wooded course with open holes mixed in, a casual stream on a couple of holes, and an OB pond to keep things interesting.
Disc Golf
Farmington Canal Heritage Trail
Hamden, Connecticut
15.1 miles SEA smooth, family-friendly rail trail perfect for an easy ride together through Hamden.
Mountain Bike
Flying Ace at Lufberry Park
Wallingford, Connecticut
15.6 miles EA well-kept free disc golf course in a quaint New England setting with a tight technical front 9 and longer holes with unique elevation on the back — open year-round at Flying Ace in Wallingford.
Disc Golf
