Skip to Main Content

The Berkshires is for Biking

Posted on March 08, 2023Written by Elizabeth Nelson, 1Berkshire
Updated on May 25, 2023

This spring, explore some of the best biking trails in the Berkshires.

As winter’s snow and ice begins to melt and the days grow longer, the Berkshire landscape prepares to bloom with the fresh air and bright colors of early spring. Soon our trails, both paved and not, will be ready for a new season of biking through forests and foothills, down rocky mountain paths, and along quaint New England Main Streets. Now is the time to plan your spring getaway – 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.

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 the 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. At 3,491 feet the peak can be chilly and windy, but the 90-mile view is worth it! Be sure to climb to the top of the Veterans War Memorial Tower.

Thrill seekers who live for the descent 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.

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.

Best Places for Biking Gear 

If you’re looking to purchase or repair a bike during your Berkshire travels, pop into 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 and Smoothie Spot 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. Don’t forget a smoothie made from locally-sourced organic fruits and veggies!

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.

Photos: Pontoosuc Lake, credit Ogden Gigli; West Stockbridge, credit Ogden Gigli 

Return to the Berkshire Blog.

In Categories

More Posts