Berkshire Day Hikes with Nature, History & Art

Discover trails where scenic landscapes meet local culture

To inspire your next outing on a Berkshire hiking trail, here’s our short list of popular outdoor spots for explorers who crave experiences as well as a view!

The High Road

Berkshire Natural Resources Council (BNRC) maintains more than sixty miles of public hiking trails county wide. The High Road project is connecting Berkshire towns with those routes via clusters of conservation land. The first segment, completed in 2021, is the eight-mile Yokun Ridge Trail from Pittsfield (Bousquet Mountain) to Lenox (Kripalu Center for Yoga & Health). Southern portions traverse Mass Audubon’s Pleasant Valley Wildlife Sanctuary.

 Appalachian National Scenic Trail (AT)

With ninety miles of footpaths running through western Massachusetts, the Berkshire section of the Appalachian Trail offers plenty of day hiking opportunities. The route is a mix of lowlands and steep terrain. Six road crossings provide easy access points for Berkshire hikers (plus parking and information kiosks).

Mt. Greylock State Reservation

Some of the Berkshire section of the Appalachian Trail runs through Mt. Greylock (elevation 3,489’). Before heading to the summit (either on foot or via the auto roads reopening spring 2025), stop at the Mt. Greylock Visitor Center for trail maps, natural history exhibits, and info about guided hikes, and kid-friendly activities. At the top, climb the spiral staircase  inside the Veteran’s War Memorial Tower for incredible views of the Berkshires and beyond (seasonal and weather permitting).

Greylock Glen, Adams

While in the Mt. Greylock area, explore woodlands, wildlife habitats, and a waterfall on the trails at Greylock Glen. Be sure to visit the new Outdoor Center, opened in October 2024 by the town of Adams as a public gathering space and learning center. Greylock Glen Executive Director Michael Wynn says, “The Center is the ideal location to start your outdoor recreation adventure on Mt. Greylock. It also allows visitors a comfortable place to return to after a day on the mountain.” Trails open dawn to dusk.

Bartholomew’s Cobble, Sheffield

For a taste of what makes springtime in the Berkshires magnificent, visit Bartholomew’s Cobble. In mid-April to May, woodland paths and open fields host a variety of ferns, blooming wildflowers, and migrating birds. Start with the natural history exhibits at the visitor center (seasonal), then go exploring. There are five miles of mapped trails. Take the Ledges Trail loop (0.5 miles) for a river walk, or hike the Tractor Path trail (0.75 miles) to Hurlburt’s Hill for sweeping views of the Housatonic River Valley. Trails open dawn to dusk.

Nature Trails at Berkshire Cultural Attractions

Visiting a Berkshire museum or historic site? Many have scenic walking trails. Head for views of Williamstown and the Green Mountains from the top of Stone Hill at The Clark. Learn about the Shakers on the universally accessible interpretive Farm & Forest Trail at Hancock Shaker Village. Or connect with the diverse ecosystem of Bartholomew’s Cobble on trails adjacent to Ashley House in Sheffield.

Berkshires Outside, photo by Christina Lane Photography.

 Also…Explore the NEW BerkshiresOutside.org

This comprehensive resource featuring 550+ outdoor recreation access points is a gem for recreation enthusiasts living in or visiting the Berkshires. Find trailheads, tent sites, bike paths, beaches, playgrounds, and more. You can search for specific interests and needs such as “family-friendly” and  “near public transit,” or search for a specific property, business, or organization.

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