38 Trails in Winchester, Massachusetts
| Rank | Trail Name | Difficulty | Length (mi) | Rating | City |
|---|---|---|---|---|---|
| 1. | Harold Parker State Forest | Advanced | 35 |   |
Andover |
| 2. | Lynn Woods Reservation | Intermediate | 0 |  |
Saugus |
| 3. | Russell Mill | Intermediate | 7.0 | |
Chelmsford |
| 4. | Middlesex Fells Reservation | Intermediate | 8.0 | |
Winchester |
| 5. | Landlocked Forest | Intermediate | 7 | |
Burlington |
| 6. | Cutler Park | Beginner | 6 | |
Newton Highlands |
| 7. | Willowdale Forest | Beginner | 20.0 | |
Wenham |
| 8. | Billerica State Forest | Intermediate | 9 | |
Billerica |
| 9. | Lowell-Dracut-Tyngsborough State Forest | Advanced | 10.0 | |
Lowell |
| 10. | Western Greenway | Intermediate | 8.0 | |
Belmont |
| 11. | Belmont Conservation | Beginner | 10.0 | |
Belmont |
| 12. | Needham Town Forest | Intermediate | 7.0 | |
Needham |
| 13. | Mill Pond Conservation Area | Intermediate | 10 | |
Burlington |
| 14. | Horn Pond | Intermediate | 13 | |
Woburn |
| 15. | Great Brook State Park | Beginner | 15.0 | |
Carlise |
| 16. | Weston College Land | Beginner | 5.0 | |
Weston |
| 17. | Hale Reservation | Beginner | 10.0 | |
Westwood |
| 18. | Georgetown-rowley State Forest | Intermediate | 9.0 | |
Georgetown |
| 19. | Bald Hill Reservation | Beginner | 10.0 | |
Boxford |
| 20. | Ward Reservation | Intermediate | 12.0 | |
Andover |
| 21. | Prospect Hill | Beginner | 10.0 | |
Waltham |
| 22. | Bradley Palmer | Beginner | 11.0 | |
Topsfield |
| 23. | Beaver Brook North | Intermediate | 4.0 | |
Belmont |
| 24. | Charles River Loop | Easiest | 15 | |
Boston |
| 25. | Merrimack River Trail | Beginner | 10.0 | |
Andover |
| 26. | Henry S. Hunnewell Town Forest | Intermediate | 1.0 | |
Natick |
| 27. | Caryl Park | Beginner | 17.0 | |
Dover |
| 28. | Whipple Hill | Beginner | 4.0 | |
Lexington |
| 29. | Great Esker Park | Intermediate | 5.0 | |
Weymouth |
| 30. | Beals Cove Park | Beginner | 5.0 | |
Hingham |
| 31. | Millenium Park | Easiest | 12.0 | |
West Roxbury |
| 32. | Jerico Town Forest | Beginner | 5.0 | |
Weston |
| 33. | Weston Aquaduct and Unused Rail Loop | 25.0 | |
Weston | |
| 34. | Littles Brook | 2.0 | |
Burlington | |
| 35. | Reading Town Forest | 5.0 | |
Reading | |
| 36. | Swan Pond Road Trails | Easiest | 7 | |
Middleton |
| 37. | Chestnut Hill Reservoir Loop | 2 | |
Boston | |
| 38. | Root Ball (Harold Parker State Forest) | 0.29 | |
Andover |
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