Rolling hills, winding country roads, and storybook villages — the Berkshires region of Western Massachusetts is more than just a pretty landscape. It’s an experience. Best known for its vibrant arts scene and pastoral beauty, the Berkshires offer something even more intimate when explored on a bicycle: a way to slow down, connect with the landscape, and experience Massachusetts one pedal stroke at a time.
There’s no wrong way to see the beautiful scenery and unique small towns of the Berkshires, but if you’ve never done it by bicycle, you’re missing out. The Berkshires provide opportunities to see art, history, and wonder to both seasoned cyclists and beginners alike. If you’re up for a ride, then grab your helmet. Here’s how you can get the most out Western Massachusetts.
Different Terrains
Across Berkshire County, which stretches from the Connecticut border to Vermont, the terrain evolves from rolling farmland to difficult mountain ascents. Rides might include quiet stretches of trails and roads as well as bustling city centers full of things to do. The variety means that there’s a suitable and enjoyable route no matter what your interests and endurance levels are.
For beginners, the Ashuwillticook Rail Trail is a good place to start. For over 14 miles between Pittsfield and Adams, this flat, paved trail passes through lakes, ponds, and four Berkshires towns along the Hoosac Valley River. There are plenty of places along the trail to pull over, take a break, and enjoy the scenery.
Intermediate and advanced cyclists can head towards Route 183 and Mount Greylock, the highest peak in Massachusetts. From Lanesborough, hop on the challenging Rockwell Road for a 10-mile climb to the mountain’s summit. You’ll be rewarded with one of the best panoramic views in Massachusetts at the top.
Along the Way
A bike ride in the Berkshires is as much about the journey as it is about your destination. The area is packed with spots to pull off road and experience regional treasures – a unique restaurant, a cultural landmark, a charming small town, and incredible scenery. Throughout the Berkshires you’ll find foliage, mountains, rivers, covered bridges, and quaint town squares. Great Barrington, Lee, and Sheffield make perfect pit stops for anyone looking to grab a bite to eat, do some local shopping, or experience a quintessential New England village.
The area is also well known for its art scene. The Norman Rockwell Museum in Stockbridge celebrates the famed American painter. The Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams is a testament to bold, modern art exhibits. The historic Tanglewood, summer home of the Boston Symphony Orchestra, is a wonderful place for a sunset concert. Becket’s Jacob’s Pillow is your stop for the spectacular art of dance.
Rider Tips
Spring and Fall are the best times to tackle the Berkshires by bicycle – the weather is pleasant and the area’s plant and wildlife really shine in the temperate climates. Weekends, especially during the busy autumn season, can be busy in the Berkshires. You might find less busy roadways during the week. Temperatures in the spring and fall can change quickly – so make sure you pack appropriately.
To explore the Berkshires by bicycle is to embrace the richness of the land, the creativity of its people, and the quiet pleasures found in a rolling descent through golden trees. Whether you’re spinning past a field of wildflowers or braking for a barn-turned-gallery, every mile tells a story.
Grab your helmet, clip in, and let the hills guide you — the Berkshires – and your bicycle – are waiting.
