13 Best Mountain Biking Trails in the Berkshires of Massachusetts

Outdoor recreation in the Berkshires of Massachusetts is the highlight of many of our guest’s stays. Whether you enjoy hiking, skiing, snowshoeing, or biking, you’ll have an easy time finding plenty of options to choose from while you enjoy the great outdoors. But if you’re looking for your next mountain biking trail to conquer, you’ve come to the right place! No matter which direction you’re heading when you set out from the Devonfield Inn in Lee, Massachusetts, you’ll find plenty of options for any skill level. Read on for our recommendations and see why a stay at Devonfield Inn is the perfect place to launch your outdoor adventures.

A mountain bike propped against a small bridge over a creek.

Going North

  • October Mountain Loop—Loop trail for intermediate riders. This much-loved trail in October Mountain State Forest is 7 miles long and features gorgeous mountain and lake views.
  • Jiminy Peak—Get lift tickets and enjoy going down the mountain on any number of intermediate and expert level trails.
  • The Boulders—Loop trail for intermediate riders. Enjoy 5.1 miles of trail with beautiful views and plenty of shade.
  • Deer Hill, Rotten Apple, Fuzzy Bunny, and Bear Claw Loop—Loop trail for any skill level. This 4-mile trail in Pittsfield State Forest brings you across creeks, near a lake, and through wooded hills.
  • Taconic Skyline Trail—Out-and-back trail for experienced riders. Enjoy 13.3 miles of breathtaking mountain views in Pittsfield State Forest that traverse a good portion of the Taconic Range. Be aware that this trail allows motorized vehicles as well as mountain bikes.White petaled wildflowers catch just a hint of sunshine.

Going South

  • Wild Cat Trail—A loop trail for any skill level. Another path in Beartown State Forest, the 5-mile journey will bring you to beautiful scenic overlooks and plentiful wildflowers in the spring.
  • Turkey Trail—An out-and-back trail for intermediate riders. Enjoy the beauty of Beartown State Forest near Great Barrington, MA on this 3.2-mile trail.
  • Hubbard River Trail—Out-and-back trail for intermediate riders. There’s a little bit of everything on this 6.1-mile trail, including wildflowers, riverside views, and beautiful, dense forest.

Going East

  • Finerty Pond via Appalachian Trail—Out-and-back trail for intermediate riders. This 5.9-mile path will take you along a beautiful pond in October Mountain State Forest.
  • Ashley Lake Loop Trail—Loop trail for all skill levels. The 3.6-mile trail is quick but full of all kinds of beauty, including views of the lake, flowers in the spring, and a variety of birds.
  • Keystone Arch Bridges Trail—An out-and-back trail for intermediate riders. Tucked into the Walnut Hill Wildlife Management Area is this 4.5-mile path through the woods that includes beautiful stone arches, river views, and a small waterfall.

Going West

  • Burbank Trail—Loop trail for intermediate riders. Take a ride on this 3.1-mile path to get excellent views of the rolling mountains and seasonal wildflowers.
  • Bowkers Woods Lower Trail—A quick, easy 1-mile loop that could make for a fun stop in between other activities.

We love offering our guests ideas for activities near our inn, and we hope you find a trail to conquer from this list! Athletes love staying at our inn because we are the perfect quiet and comfortable place to come “home” to after a day of strenuous exercise. Between our delicious evening snacks, our delightfully comfortable beds, and our gourmet breakfasts ready for you each morning, there’s just no better place to call home in the Berkshires. Book a stay with us today and see where your heart takes you!

Gathering around the fire pit to enjoy the outdoors in the Berkshires