Top Ten Mountain Biking Trails in the Berkshires

Spring is about to pop in the Berkshires. Which means, of course, it’s time to start planning your outdoor adventures. The rolling hills of western Massachusetts offers so much in the way of open-air activities. It’s a virtual mecca for anyone who loves exploring the great outdoors. Chit chat around the breakfast table at our bed and breakfast in Sheffield, MA often turns to tales of great days spent skiing, hiking, or snowshoeing in winter. But come spring, for serious cyclists at least, the overwhelming desire is to tune up their road bikes and tackle a challenging mountain biking trail.

two hands gripping bike riding through green forest on a dirt pathSeveral organizations in the Berkshires, along with avid local cyclists, work to make our network of mountain trails truly accessible and always well-maintained. While you’re certain to find easy-going trails, the more challenging switchback routes with technical log and rock features are not for the faint of heart.

It helps to know what you’re in for when heading out to do some biking in the mountains of the Berkshires. So, here in a nutshell, are ten of the most popular trails to explore on your next visit. Most trail heads start within a 30- to 50-minute ride from us in Sheffield.

Beartown State Forest

Located in nearby Great Barrington, MA, Beartown State Forest is a popular spot for cyclists of all skill levels. Several easy to moderate trails of varying lengths offer views of Benedict Pond, scenic overlooks, and spring wildflowers.

Bowkers Wood Lower Trail

An easy 1-mile trail located near Stockbridge featuring river views. Keep a look out for Canadian Geese, Blue Heron, and Wood Ducks that frequent the wetlands.

Burbank Trail

Best for those with intermediate skills, this trail is popular in spring for its abundance of wildflowers. Rated moderate, the Burbank trail leads to a beautiful vista at Olivia’s Overlook.

The Boulders

Another moderate trail for intermediate cyclists, the Boulders 5.1-mile loop trail leads to a stunning view from the boulders at the summit. Marked red, green, and blue routes connect to offer easy short rides, to more difficult moderate cycling along a stream and around a pond.

Finerty Pond via the Appalachian Trail

This nearly 6-mile track is out and back trail in deep woods that leads to a pond. Located near Becket, MA, this is the perfect summer trek mostly in shade with a stop to cool off in Finerty Pond.

Hubbard River Trail

Another out and back trail 6.1 miles in length best for intermediate riders. Spring wildflowers and dense forest characterize this route.

Jiminy Peak

Featuring a mix of single-track and downhill cruising, the trails at Jiminy Peak are served by lifts. Best suited for experienced mountain bikers, just bring your bike and buy a lift ticket for a thrill ride down the mountain.

Keystone Arch Bridges Trail

Serious mountain bikers love this trail. Features include stone arches, a small waterfall, and views of the river below. A 5-mile out and back trail located near Chester, MA located in the Walnut Hill Wildlife Management Area, can be challenging due to wet conditions and mud.

October Mountain Loop

One of many trails located in October Mountain State Forest, this well-loved loop trail offers 6 miles of challenging steep climbs. Along the way you’ll pass babbling brooks and views of Felton Lake.

Pittsfield State Forest Trails

Pittsfield State Forest offers a multitude of mountain biking trails suitable for all skill levels. Choose your route from easy to moderate, from lengths of 3- to 11-miles.

After a strenuous day out and about on any one of the top ten mountain biking trails in the Berkshires, come back to your quiet and cozy lodging at the Staveleigh House Bed and Breakfast. With 7 charming rooms, all with private bath, it’s the perfect place to call home on your visit to the Berkshires.

For more on great biking in the Berkshires, read our previous post, Biking in the Berkshires.