25 Trails in Middlebury, Connecticut

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

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