32 Trails in Upton, Massachusetts

Rank Trail Name Difficulty Length (mi) Rating City
1. Vietnam Trails Intermediate difficulty 20.0 **** Milford
2. Diamond Hill State Park Advanced difficulty 10.0 ***** Cumberland
3. Mt. Pisgah Intermediate difficulty 8.0 **** Northborough
4. Rayburn Trails Intermediate difficulty 10.0 **** Millbury
5. Singletary Trails Intermediate difficulty 15.0 **** Millbury
6. Callahan State Park Beginner difficulty 10.0 **** Framingham
7. Plummer's Landing/ Goat Hill Advanced difficulty 15.0 **** Whitinsville
8. Douglas State Forest Intermediate difficulty 27.0 **** Douglas
9. Sutton State Forest Intermediate difficulty 12.0 **** Sutton
10. Hopkinton State Park Intermediate difficulty 10.0 **** Hopkinton
11. Franklin State Forest Intermediate difficulty 7.0 **** Franklin State Forest
12. West Hill Dam Intermediate difficulty 5.0 **** Upton
13. Ashland State Park Intermediate difficulty 7.0 *** Ashland
14. Upton State Forest Beginner difficulty 12.0 *** Upton
15. Grafton Land Trust Intermediate difficulty 20.0 *** Grafton
16. Mendon Town Forest Intermediate difficulty 7.0 **** Mendon
17. Walkabout Trail/george Washington Management Area Intermediate difficulty 8.0 *** Chepachet
18. Nobscot Mtn. Intermediate difficulty 15.0 *** Sudbury
19. Cold Harbor Brook Intermediate difficulty 5.0 *** Northborough
20. Beaver Pond Advanced difficulty 7.0 **** Franklin
21. Lake Whitehall Advanced difficulty 7.0 *** Hopkinton
22. Green Hill Park Advanced difficulty 5.0 **** Worcester
23. Middle School Loop Beginner difficulty 3.0 *** Nasonville
24. Peppercorn Hill Intermediate difficulty 3.0 *** Upton
25. Yellow Beginner difficulty 5.0 *** Worcester
26. Boy Scout Trails Intermediate difficulty 2.0 *** Franklin
27. Gardner Hill Town Forest Intermediate difficulty 6.0 *** Stow
28. Weston Aquaduct and Unused Rail Loop difficulty 25.0 Weston
29. Newton Hill Easiest difficulty 2.0 ** Worcester
30. Colt Farm difficulty 5.0 North Smithfield
31. Black Hut Management Area difficulty 11.0 Glendale
32. Libby Trail difficulty 4.0 Westborough

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