32 Trails in Milton, Massachusetts

Rank Trail Name Difficulty Length (mi) Rating City
1. Lynn Woods Reservation Intermediate difficulty 0 **** Saugus
2. Middlesex Fells Reservation Intermediate difficulty 8.0 **** Winchester
3. Landlocked Forest Intermediate difficulty 7 **** Burlington
4. Wompatuck State Park Intermediate difficulty 15.0 **** Hingham
5. Cutler Park Beginner difficulty 6 **** Newton Highlands
6. F. Gilbert Hills State Park Intermediate difficulty 11.0 **** Foxboro
7. Blue Hills Intermediate difficulty 5.0 **** Milton
8. Borderland State Park Intermediate difficulty 7.0 **** Sharon
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. Wrentham State Forest Advanced difficulty 17.0 ***** Wrentham
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. Prospect Hill Beginner difficulty 10.0 **** Waltham
18. Ames Nowell Intermediate difficulty 10.0 *** Abington
19. Beaver Brook North Intermediate difficulty 4.0 **** Belmont
20. Charles River Loop Easiest difficulty 15 ** Boston
21. Caryl Park Beginner difficulty 17.0 *** Dover
22. Whitney And Thayer Woods/weir River Farm Beginner difficulty 10.0 *** Cohasset
23. Whipple Hill Beginner difficulty 4.0 *** Lexington
24. Noon Hill Reservation Beginner difficulty 8.0 *** Medfield
25. World's End Beginner difficulty 5.0 *** Hingham
26. Rocky Woods Beginner difficulty 7.0 ** Medfield
27. Great Esker Park Intermediate difficulty 5.0 ** Weymouth
28. Beals Cove Park Beginner difficulty 5.0 ** Hingham
29. Millenium Park Easiest difficulty 12.0 * West Roxbury
30. Jerico Town Forest Beginner difficulty 5.0 ** Weston
31. Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
32. Chestnut Hill Reservoir Loop difficulty 2 Boston

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