221 Trails in Massachusetts

Rank Trail Name Difficulty Length (mi) Rating City
1. Wolftree trail, Bittersweet,Dragon tail, Dave's Pass, Moonwort difficulty 6.0 Adams
2. Rock wood difficulty 0.2 Mendon
3. Nick difficulty 5.0 Rockport
4. Boy Scout Trails difficulty 2.0 Franklin
5. Cranberry pond difficulty 15.0 Braintree
6. Dracut conservation trail difficulty 2.0 Dracut
7. Carver Conservation Area difficulty 10.0 Carver
8. Special Ops (♦) difficulty 0.68 Groton
9. Root Ball (Harold Parker State Forest) difficulty 0.29 Andover
10. Sha-nah-nah difficulty 0.0 Wilbraham
11. Brake Hill (West Newbury / Groveland) difficulty 4 Groveland
12. Chestnut Hill Reservoir Loop difficulty 2 Boston
13. Tisbury Meadow difficulty 7.0 Vineyard Haven
14. Race Leading difficulty 4.0 Amherst
15. Old Rifle Range difficulty 2.0 Concord, Ma
16. Chesterfield Gorge difficulty 8.0 Chesterfield
17. General Hobbs loop difficulty 6.0 Holden
18. Sugarloaf Mt/Pucumtuck trail difficulty 5.0 South Deerfield
19. John Hyslip difficulty 3.0 Andover
20. Noon hill difficulty 2.0 Medfield
21. Hampshire College difficulty 4.0 Amherst
22. Chesterfield Gorge difficulty 8.0 Chesterfield
23. Springside park difficulty 4.0 Pittsfield
24. Fort Rock difficulty 7.0 Littleton
25. The Groton Wildlife Sanctury/Lawrence Woods difficulty 10.0 Groton
26. Tantasqua jr high difficulty 15.0 Fiskdale
27. Libby Trail difficulty 4.0 Westborough
28. Bruce and toms difficulty 15.0 Gloucester
29. Altar rock difficulty 10.0 Nantucket
30. Moore State Park difficulty 2.0 Rutland/leicester
31. Brimfield State Forest difficulty 20.0 Brimfield
32. Beech Saint Conservation Land difficulty 2.0 Rockland
33. Swan Pond Road Trails Easiest difficulty 7 ** Middleton
34. Ayer to Nashua Rail Trail Beginner difficulty 16.0 Pepperell
35. Conant Brook Dam difficulty 0.0 Palmer
36. Corridor 71 New Braintree difficulty 6.0 New Braintree
37. Corridor 71 difficulty 10.0 Spencer
38. Knightville Dam difficulty 0.0 Westfield
39. Boxboro Trail link-up difficulty 8.0 Boxboro
40. South Groton Trails difficulty 10.0 Groton
41. Reading Town Forest difficulty 5.0 Reading
42. Covered Bridge difficulty 3.0 Barre
43. Unknown difficulty 3.0 Hadley
44. Chaug Path difficulty 1.0 Wilbraham
45. Mt Watatic difficulty 8.0 Ashby
46. Sandy Neck Beach difficulty 10.0 Barnstable
47. Pearly Brook Loop difficulty 15.0 Gardner
48. Provin Mountain difficulty 3.0 Feeding Hills
49. Whites Reservior difficulty 16.0 Westhampton
50. Gregg Woods difficulty 5.0 Dunstable

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