221 Trails in Massachusetts

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