45 Trails in Natick, Massachusetts

Rank Trail Name Difficulty Length (mi) Rating City
1. Vietnam Trails Intermediate difficulty 20.0 **** Milford
2. Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
3. Landlocked Forest Intermediate difficulty 7 **** Burlington
4. Cutler Park Beginner difficulty 6 **** Newton Highlands
5. F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
6. Blue Hills Intermediate difficulty 5.0 **** Milton
7. Borderland State Park Intermediate difficulty 7.0 **** Sharon
8. Callahan State Park Beginner difficulty 10.0 **** Framingham
9. Adams Farm Intermediate difficulty 10.0 **** Walpole
10. Western Greenway Intermediate difficulty 8.0 **** Belmont
11. Belmont Conservation Beginner difficulty 10.0 *** Belmont
12. Needham Town Forest Intermediate difficulty 7.0 *** Needham
13. Mill Pond Conservation Area Intermediate difficulty 10 **** Burlington
14. Horn Pond Intermediate difficulty 13 **** Woburn
15. Weston College Land Beginner difficulty 5.0 **** Weston
16. Hale Reservation Beginner difficulty 10.0 **** Westwood
17. Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
18. Franklin State Forest Intermediate difficulty 7.0 **** Franklin State Forest
19. West Hill Dam Intermediate difficulty 5.0 **** Upton
20. Ashland State Park Intermediate difficulty 7.0 *** Ashland
21. Prospect Hill Beginner difficulty 10.0 **** Waltham
22. Upton State Forest Beginner difficulty 12.0 *** Upton
23. Mendon Town Forest Intermediate difficulty 7.0 **** Mendon
24. Oak Hill Advanced difficulty 8.0 **** Littleton
25. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
26. Charles River Loop Easiest difficulty 15 ** Boston
27. Henry S. Hunnewell Town Forest Intermediate difficulty 1.0 ***** Natick
28. Caryl Park Beginner difficulty 17.0 *** Dover
29. Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
30. Rattlesnake Hill Advanced difficulty 7.0 ***** Bolton
31. Whipple Hill Beginner difficulty 4.0 *** Lexington
32. Boxborough Area Trails Intermediate difficulty 10.0 *** Boxborough
33. Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
34. Beaver Pond Advanced difficulty 7.0 **** Franklin
35. Rocky Woods Beginner difficulty 7.0 ** Medfield
36. Lake Whitehall Advanced difficulty 7.0 *** Hopkinton
37. Peppercorn Hill Intermediate difficulty 3.0 *** Upton
38. Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
39. Gardner Hill Town Forest Intermediate difficulty 6.0 *** Stow
40. Millenium Park Easiest difficulty 12.0 * West Roxbury
41. Jerico Town Forest Beginner difficulty 5.0 ** Weston
42. Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
43. Littles Brook difficulty 2.0 Burlington
44. Fort Rock difficulty 7.0 Littleton
45. Chestnut Hill Reservoir Loop difficulty 2 Boston

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