221 Trails in Massachusetts
| Trail Name | Difficulty | Length (mi) | Rating | City |
|---|---|---|---|---|
| Yellow | Beginner | 5.0 |    |
Worcester |
| Wrentham State Forest | Advanced | 17.0 | |
Wrentham |
| World's End | Beginner | 5.0 | |
Hingham |
| Wompatuck State Park | Intermediate | 15.0 | |
Hingham |
| Wolftree trail, Bittersweet,Dragon tail, Dave's Pass, Moonwort | 6.0 | |
Adams | |
| Wma Trail | Beginner | 3.0 | |
Wilbraham |
| Willowdale Forest | Beginner | 20.0 | |
Wenham |
| Willow Street Trails | Intermediate | 15.0 | |
Yarmouth |
| Wilbraham/Hampden Loop | Intermediate | 6.0 | |
Springfield |
| Whitney And Thayer Woods/weir River Farm | Beginner | 10.0 | |
Cohasset |
| Whites Reservior | 16.0 | |
Westhampton | |
| Whipple Hill | Beginner | 4.0 | |
Lexington |
| Weston College Land | Beginner | 5.0 | |
Weston |
| Weston Aquaduct and Unused Rail Loop | 25.0 | |
Weston | |
| Western Greenway | Intermediate | 8.0 | |
Belmont |
| West Hill Dam | Intermediate | 5.0 | |
Upton |
| West Barnstable Conservation Area | Intermediate | 12.0 | |
West Barnstable |
| Wendell State Forest | Intermediate | 17.0 | |
Wendell |
| Wells State Park | Intermediate | 10.0 | |
Sturbridge |
| Wellfleet Ponds | Beginner | 20.0 | |
Wellfleet |
| Weir hill | Easiest | 5.0 | |
North Andover |
| Waskosims Rock | 5.0 | |
West Tisbury | |
| Ware River Rail trail | 7.0 | |
Barre | |
| Ward Reservation | Intermediate | 12.0 | |
Andover |
| Volunteer Park/Chatham Ponds | Beginner | 7.0 | |
Chatham |
| Village Park/ Abrams Rock | Intermediate | 5.0 | |
Swansea |
| Vietnam Trails | Intermediate | 20.0 | |
Milford |
| Vaughn Hill/bower Spring Trail System(s) | Advanced | 4.0 | |
Bolton/harvard |
| Upton State Forest | Beginner | 12.0 | |
Upton |
| Unknown | 3.0 | |
Hadley | |
| Tully Lake | Advanced | 0.0 | |
Royalston |
| Townsend State Forest | Beginner | 15.0 | |
Townsend |
| Tisbury Meadow | 7.0 | |
Vineyard Haven | |
| Thunder Mountain Bike Park (Berkshire East) | Advanced | 5.0 | |
Charlemont |
| The Groton Wildlife Sanctury/Lawrence Woods | 10.0 | |
Groton | |
| The Boulders | Beginner | 6.0 | |
Dalton |
| Tantasqua jr high | 15.0 | |
Fiskdale | |
| Talbot Trails | Advanced | 8.0 | |
Northboro |
| Swan Pond Road Trails | Easiest | 7 | |
Middleton |
| Sutton Water Works | Intermediate | 5.0 | |
Sutton |
| Sutton State Forest | Intermediate | 12.0 | |
Sutton |
| Sugarloaf Mt/Pucumtuck trail | 5.0 | |
South Deerfield | |
| Springside park | 4.0 | |
Pittsfield | |
| Special Ops (♦) | 0.68 | |
Groton | |
| South Groton Trails | 10.0 | |
Groton | |
| Singletary Trails | Intermediate | 15.0 | |
Millbury |
| Sheep Pond Woodland Hills Conservation | 3.0 | |
Brewster | |
| Shawme-Crowell State Forest | 10.0 | |
Sandwich | |
| Sha-nah-nah | 0.0 | |
Wilbraham | |
| Sawmill Hills Conservation Area | Intermediate | 8.0 | |
Northampton |
