27 Trails in Cheshire, Connecticut
| Trail Name | Difficulty | Length (mi) | Rating | City |
|---|---|---|---|---|
| Westwoods | Intermediate | 30.0 |   |
Guilford |
| Rockland Preserve | Intermediate | 25.0 | |
Madison |
| Sessions Woods | 20.0 | |
Burlington | |
| Cheshire Lock 12 | Easiest | 18.0 | |
Cheshire |
| Nassahegan State Forest | Intermediate | 15.0 |  |
Burlington |
| West Rocks State Park | Intermediate | 12.0 | |
New Haven |
| Rockhouse Hill Sanctuary | Intermediate | 12.0 | |
Oxford |
| Racebrook Tract | 11.0 | |
Middletown | |
| Supply Ponds | Intermediate | 10.0 | |
Branford |
| Stony Creek Quarry Preserve | Intermediate | 10.0 | |
Branford |
| Tyler Mills | Intermediate | 10.0 | |
Wallingford |
| Genesee Recreation Area | Beginner | 10.0 | |
Madison |
| Brooksvale Park And Naugatuck State Forest | Advanced | 10.0 | |
Hamden |
| Larkin State Bridal Trail | Easiest | 10.0 | |
Southbury |
| West Hartford Reservoir | Intermediate | 10.0 | |
West Hartford |
| Middlebury Greenway | Easiest | 10.0 | |
Middlebury |
| Crescent Lake | Intermediate | 6 | |
Southington |
| Yale Preserve | Intermediate | 6.0 | |
Woodbridge |
| Winding Trails | Beginner | 5.0 | |
Farmington |
| East Rock Park | Intermediate | 5.0 | |
New Haven |
| Timberlands | 5.0 | |
Madison | |
| Millers Pond | Advanced | 5.0 | |
Durham |
| Farmington Canal Heritage Trail | Easiest | 5.0 | |
Hamden |
| Wadsworth State Park | Intermediate | 5.0 | |
Middletown |
| Thomaston Dam | Easiest | 0.0 | |
Thomaston |
| Powder Ridge Bike Park | Intermediate | 0 | |
Middlefield |
| Rockwell Park | 0 | |
Bristol |