The Berkshires is for Biking

This summer, explore the Berkshires by bike trail – one of the best ways to see this incredible region

As bright spring days grow longer with New England sunshine, the Berkshire landscape begins to bloom with the fresh air and vibrant colors of the prime, warm weather season. Soon our trails, both paved and not, will be ready for visitors and residents – those on foot and on wheels. Biking is a great way to experience the beauty of the Berkshires. Challenge yourself on trails winding through forests and down rocky paths, or meander leisurely along quaint Main Streets and scenic rail trails where you can pause to admire lake views. Now is the time to plan your getaway to come bike in the Berkshires!

Biking enthusiasts and newbie peddlers alike will find trails tailored to their skill level. Whether you arrive with all your gear in tow or you’re trying mountain biking for the first time and need a lesson and a rental bike, the region offers a host of options. Read on for ideas to make the most of your Berkshire biking trip.

Photo by Christina Lane Photography.

Best Biking Trails in the Berkshires

Did you know that the Berkshires is home to the highest point in Massachusetts and you can bike to this impressive summit? If you’re looking for a challenging ride with fantastic views, heart-stopping hairpin turns, and thrilling downhill coasts, you’ll want to check out Mount Greylock. Tackle the ride from either North Adams (more challenging) or Lanesborough. Wear layers during cooler seasons and times of day. At 3,491 feet the peak can be windy, but the 90-mile, multi-state view is worth it! Be sure to climb to the top of the Veterans War Memorial Tower before starting your descent.

Thrill seekers won’t want to miss Berkshire East’s Thunder Mountain Bike Park, a gravity downhill park featuring purpose-built trails, from introductory to pro-line jump. Lessons are recommended to make the most of your experience, and proper bicycles and gear are available to rent. Also, keep an eye out for the Shaker Ridge Trails, coming soon to the Berkshires! Located in Hancock and Lanesborough, this mountain biking destination will offer over 25 miles of professionally crafted paths, perfect for mountain bikers of all ages and skill levels to enjoy.

October Mountain is the largest state forest in Massachusetts and one of the most beautiful. Local cyclists recommend the October Mountain Loop, a 7-mile trail ideal for intermediate riders looking to enjoy views of mountains and lakes. Experience a similar option in the Pittsfield State Forest on the 8-mile Snoopy Loop, or if you’re looking for a longer ride, check out this 20-mile road route encompassing the Alford Loop and back. We recommend downloading trail maps or a cycling app for details.

Managed by Berkshire Natural Resource Council, The Boulders is a property spanning 645 acres complete with 6 miles of trails for bikers, hikers, and dog walkers. Choose between the easy Heart Healthy Loop or moderate Blue and Red trails. The Boulders is an excellent location for shade and birdwatching. Ride to the top of the Blue trail to see the dramatic rocks for which the property is named.

Looking for a group ride? In October 3-5, 2025, PMC Unpaved will offer two fully-supported routes of 30 or 50 miles. This bike-a-thon raises funds for cancer research and treatment at Dana-Farber Cancer Institute. The weekend starts with a Friday night campfire followed by a Saturday ride and then fun at Camp Mah-Kee-Nac in Lenox.

For a paved path, ride the Ashuwillticook Rail Trail, which you can access at various points in the Berkshires. Along the way you’ll see waterways, forests, and local wildlife. If you cycle through the section in Cheshire, stop into Common Table for lunch or a craft cocktail.

Photo by Great Sky Media.

Best Places for Biking Gear 

Purchase or repair your bike during your Berkshire travels at Berkshire Bike & Board, located in both Pittsfield and Great Barrington. Sporting a team of passionate cyclists, you’ll be in good hands picking out the best ride for your trip and/or lifestyle. Both shops offer free test rides in varied styles and sizes. Throughout the warm weather seasons, Berkshire Bike & Board offer group rides and other events, plus they offer an expertly curated list of routes around the region. 

Another great place to shop is the Arcadian Shop where you can outfit all your outdoor adventures from biking to water sports and beyond. You can purchase road, mountain, hybrid, electric, and kid’s bikes, as well as accessories, clothing, footwear, and energy bars. After your bike ride, cool off on a Berkshire lake with a paddle board or kayak – the shop rents out both.

While geared more toward hiking, Nature’s Closet is still an excellent stop for high quality outdoor clothing and accessories. Find shoes, packs, water bottles and more to make your rides as smooth as possible. 

Speaking of snacks…before riding into your adventure, pack a picnic of fresh, locally-grown and made goodies from any of our specialty food markets like Guido’s, High Lawn Farm, The Marketplace Specialty Store, and Lanesborough Local.

We encourage you to keep exploring as you plan your Berkshire getaway. Find inspiration for things to do, places to stay, and where to find amazing eats, shopping experiences, wellness retreats, and more in the Berkshires. Visit BerkshiresOutside.org for even more inspo!

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