The Best Hiking Areas and Bike Trails in the Berkshires

Getting back to nature is never more beautiful than when you’re enjoying the great outdoors in the Berkshires. You’ll find paddle boarding, kayaking, fishing and boating, but sometimes all you want to do is go for a peaceful hike or bike ride. Whether you’re looking to feel the wind in your hair, stroll by the water, or conquer a rocky trail, this list of the best hiking areas and biking trails in the Berkshires has exactly what you need.


Ashuwillticook Rail Trail

This former railroad corridor turned hiker’s paradise runs parallel to Route 8, meandering through the scenic towns of Cheshire, Lanesborough and Adams, ending in the middle of the latter spot. The entire trail is about 11.2 miles long, and it’s about 10 feet wide, leaving plenty of room for bikers, hikers, walkers and runners of all ages to do their thing. You can start at the beginning (the southern tip of the trail starts at the Berkshire Mall in Lanesborough- right across from The Lake House Guest Cottages of the Berkshires), or take advantage of the parking lots situated conveniently at various points along the trail. There are restrooms, tucked in amongst the numerous incredible views of everything from the mountains to the wetlands, including lots of wildlife.

Housatonic Bike Routes

For those who might eschew hiking in favor of a day on the bike trails, this 45-mile route could be the answer. The trail starts in New Milford to the south and runs north to Ashley Falls, Massachusetts, encompassing a wide variety of terrain in the process. As riders huff it through tough climbs and coast over dirt roads, they can see everything from working farms to waterfalls. It’s a great way to get a feel for both the topography and day-to-day life in the region, and the views are glorious, too.

The Appalachian Trail

Many people associate the Appalachian Trail with a region somewhere south of Massachusetts, but the legendary path actually runs more than 2,000 miles from Georgia to Maine. The Massachusetts section of the trail snakes through some incredibly scenic spots, including Race Brooks Falls, the imposing and impressive hardwood forests in the western part of the state, and, of course, Mt. Greylock. The listing provided by breaks the Appalachian Trail down into smaller hikes ideal for Berkshire residents and tourists alike, so you can tailor your hike to the amount of time you have to spare.

River’s Edge Cycling

If you’re looking to combine biking with a guided tour, the experts at River’s Edge Cycling can help you discover the very best bits of the Berkshires without any fear of missing out on something great (or getting lost). The company arranges both single-day trips and multi-day tours – perfect for beginners and biking clubs alike – and they’ll happily customize trips around your preferences or schedule as well.

Housatonic River Walk

As the name suggests, Great Barrington’s Housatonic River Walk follows the Housatonic River as it winds its way through Great Barrington. The trail isn’t long, but that just makes it a pleasant place to go for a leisurely excursion with the kids without worrying about tiring out the little ones (or yourself). You will also see two historic places to visit along the way: W.E.B. Du Bois River Park was built to honor one of the river’s biggest protectors, and William Stanley Overlook blends a bit of Great Barrington history with the beauty of a native garden.

Note that the River Walk is closed during the winter, but the springtime re-opening (generally taking place in mid- or late-April) is an event in itself, with volunteers helping to clean the trail and make it a safe place for adventurers of all ages.

Becket Land Trust – Historic Quarry and Forest

The Becket Land Trust was formed in 1991 by a group of concerned citizens who sought to preserve the character and natural resources that abound in the town. Thanks to a phenomenal fundraising effort by the local community, the trust was able to purchase more than 300 acres, preserving the land and turning it into a public property perfect for hiking, exploring and general merrymaking. The forest preserve has a demonstration forest, tons of trails (ideal for hiking or cross-country skiing), and lots of beautiful plants and wildlife. On the quarry side, visitors can take a self-guided tour through various relics that harken back to a time when the quarry was a major source of rock used to build many of the local Berkshire towns.


This route isn’t for amateurs or the athletically disinclined, and it promises to be a lot of hard work, but the payoff is unparalleled. As the highest mountain in Massachusetts, Greylock comes with some serious altitude, but that doesn’t stop committed bikers. A path goes right over the mountain and a counterclockwise loop as well. Both begin at Williamstown Public Library, so you can decide which itinerary you’d like to conquer.

Mass Audubon’s Pleasant Valley Wildlife Sanctuary

For people who like to share their hikes with a bevy of woodland and waterfront creatures, the Pleasant Valley Wildlife Sanctuary is going to be a splendid surprise. The retreat runs over more than 1,000 abundantly green acres, with forests flowing into meadows that abut wetlands as well as the sloping sides of Lenox Mountain. The trails range in difficulty, so there truly is something for everyone; if you need to catch your breath, there’s no better way to do it than to sit quietly and watch the resident beavers hard at work building their lodges and dams.

Whether you’re planning to hike, bike or simply stroll your way through the beautiful Berkshires, make your base camp the cozy and well-appointed guest cottages at The Lake House. Our lakeside retreat offers stunning views, gas fireplaces, fully equipped kitchens and plenty of superb amenities – everything you need to enjoy your sojourn in the mountains of Western Massachusetts!