25 Trails in Middlebury, Connecticut

Trail Name Difficulty Length (mi) Rating City
Rockwell Park 0 Bristol
Thomaston Dam Easiest 0.0 *** Thomaston
East Rock Park Intermediate 5.0 ***** New Haven
Winding Trails Beginner 5.0 *** Farmington
Farmington Canal Heritage Trail Easiest 5.0 * Hamden
Funny Farm North Beginner 5.0 * Newtown
Yale Preserve Intermediate 6.0 ***** Woodbridge
Lower Paugussett State Forest 6.0 Newtown
Upper Paugussett State Forest 6.0 Newtown
Dingle Brook Trail 6.0 *** Newtown
Trumbull Rail Trail Easiest 6.0 ** Trumbull
George C Waldo St Park Intermediate 7.0 ***** Southbury
Steep Rock Advanced 7.0 **** Washington
Monroe Rail Trail 8.0 Monroe
Middlebury Greenway Easiest 10.0 **** Middlebury
Brooksvale Park And Naugatuck State Forest Advanced 10.0 ** Hamden
Larkin State Bridal Trail Easiest 10.0 **** Southbury
Racebrook Tract 11.0 *** Middletown
West Rocks State Park Intermediate 12.0 *** New Haven
Rockhouse Hill Sanctuary Intermediate 12.0 ***** Oxford
Nassahegan State Forest Intermediate 15.0 ***** Burlington
Pequonnock River Valley State Park / Trumbull Intermediate 15.0 ***** Trumbull
Cheshire Lock 12 Easiest 18.0 ***** Cheshire
Sessions Woods 20.0 *** Burlington
Collis P Huntington State Park Intermediate 20.0 *** Bethel