38 Trails in Dover, Massachusetts
| Rank | Trail Name | Difficulty | Length (mi) | Rating | City |
|---|---|---|---|---|---|
| 1. | Vietnam Trails | Intermediate | 20.0 |   |
Milford |
| 2. | Diamond Hill State Park | Advanced | 10.0 |  |
Cumberland |
| 3. | Middlesex Fells Reservation | Intermediate | 8.0 | |
Winchester |
| 4. | Landlocked Forest | Intermediate | 7 | |
Burlington |
| 5. | Cutler Park | Beginner | 6 | |
Newton Highlands |
| 6. | F. Gilbert Hills State Park | Intermediate | 11.0 | |
Foxboro |
| 7. | Blue Hills | Intermediate | 5.0 | |
Milton |
| 8. | Borderland State Park | Intermediate | 7.0 | |
Sharon |
| 9. | Callahan State Park | Beginner | 10.0 | |
Framingham |
| 10. | Adams Farm | Intermediate | 10.0 | |
Walpole |
| 11. | Western Greenway | Intermediate | 8.0 | |
Belmont |
| 12. | Belmont Conservation | Beginner | 10.0 | |
Belmont |
| 13. | Needham Town Forest | Intermediate | 7.0 | |
Needham |
| 14. | Wrentham State Forest | Advanced | 17.0 | |
Wrentham |
| 15. | Horn Pond | Intermediate | 13 | |
Woburn |
| 16. | Weston College Land | Beginner | 5.0 | |
Weston |
| 17. | Hopkinton State Park | Intermediate | 10.0 | |
Hopkinton |
| 18. | Hale Reservation | Beginner | 10.0 | |
Westwood |
| 19. | Franklin State Forest | Intermediate | 7.0 | |
Franklin State Forest |
| 20. | Ashland State Park | Intermediate | 7.0 | |
Ashland |
| 21. | Prospect Hill | Beginner | 10.0 | |
Waltham |
| 22. | Beaver Brook North | Intermediate | 4.0 | |
Belmont |
| 23. | Charles River Loop | Easiest | 15 | |
Boston |
| 24. | Henry S. Hunnewell Town Forest | Intermediate | 1.0 | |
Natick |
| 25. | Caryl Park | Beginner | 17.0 | |
Dover |
| 26. | Nobscot Mtn. | Intermediate | 15.0 | |
Sudbury |
| 27. | Whipple Hill | Beginner | 4.0 | |
Lexington |
| 28. | Boxborough Area Trails | Intermediate | 10.0 | |
Boxborough |
| 29. | Noon Hill Reservation | Beginner | 8.0 | |
Medfield |
| 30. | Beaver Pond | Advanced | 7.0 | |
Franklin |
| 31. | Rocky Woods | Beginner | 7.0 | |
Medfield |
| 32. | Boy Scout Trails | Intermediate | 2.0 | |
Franklin |
| 33. | Gardner Hill Town Forest | Intermediate | 6.0 | |
Stow |
| 34. | Millenium Park | Easiest | 12.0 | |
West Roxbury |
| 35. | Jerico Town Forest | Beginner | 5.0 | |
Weston |
| 36. | Weston Aquaduct and Unused Rail Loop | 25.0 | |
Weston | |
| 37. | Littles Brook | 2.0 | |
Burlington | |
| 38. | Chestnut Hill Reservoir Loop | 2 | |
Boston |
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