27 Trails in Cheshire, Connecticut
| Rank | Trail Name | Difficulty | Length (mi) | Rating | City |
|---|---|---|---|---|---|
| 1. | Rockland Preserve | Intermediate | 25.0 |   |
Madison |
| 2. | Millers Pond | Advanced | 5.0 |  |
Durham |
| 3. | Nassahegan State Forest | Intermediate | 15.0 | |
Burlington |
| 4. | West Hartford Reservoir | Intermediate | 10.0 | |
West Hartford |
| 5. | Westwoods | Intermediate | 30.0 | |
Guilford |
| 6. | Wadsworth State Park | Intermediate | 5.0 | |
Middletown |
| 7. | Crescent Lake | Intermediate | 6 | |
Southington |
| 8. | Larkin State Bridal Trail | Easiest | 10.0 | |
Southbury |
| 9. | Tyler Mills | Intermediate | 10.0 | |
Wallingford |
| 10. | West Rocks State Park | Intermediate | 12.0 | |
New Haven |
| 11. | Winding Trails | Beginner | 5.0 | |
Farmington |
| 12. | East Rock Park | Intermediate | 5.0 | |
New Haven |
| 13. | Rockhouse Hill Sanctuary | Intermediate | 12.0 | |
Oxford |
| 14. | Supply Ponds | Intermediate | 10.0 | |
Branford |
| 15. | Yale Preserve | Intermediate | 6.0 | |
Woodbridge |
| 16. | Cheshire Lock 12 | Easiest | 18.0 | |
Cheshire |
| 17. | Sessions Woods | 20.0 | |
Burlington | |
| 18. | Middlebury Greenway | Easiest | 10.0 | |
Middlebury |
| 19. | Genesee Recreation Area | Beginner | 10.0 | |
Madison |
| 20. | Powder Ridge Bike Park | Intermediate | 0 | |
Middlefield |
| 21. | Stony Creek Quarry Preserve | Intermediate | 10.0 | |
Branford |
| 22. | Racebrook Tract | 11.0 | |
Middletown | |
| 23. | Brooksvale Park And Naugatuck State Forest | Advanced | 10.0 | |
Hamden |
| 24. | Thomaston Dam | Easiest | 0.0 | |
Thomaston |
| 25. | Farmington Canal Heritage Trail | Easiest | 5.0 | |
Hamden |
| 26. | Rockwell Park | 0 | |
Bristol | |
| 27. | Timberlands | 5.0 | |
Madison |
Know of a new mountain bike trail not listed here? Please tell us about it using this form. Find mountain bike trails near you or for even more trail inspiration and how we ranked the mountain bike trails, see this list of the best mountain bike trails in the world.
