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6 Beautiful Hiking Spots with Nature, History & Culture

Posted on March 02, 2024Written by Nancy Macy on behalf of 1Berkshire
Updated on March 21, 2024

Two people stroll along the path at Pleasant Valley surrounded by green trees, grass, and water

Take a day hike that combines a breath of fresh air with learning something new.

There are 800 mapped trails in the Berkshires. To inspire your next outing, here’s our short list of popular hiking places for explorers who crave experiences as well as stunning scenery.

Appalachian National Scenic Trail (AT)

With ninety miles of footpaths running through western Massachusetts, the Berkshire section of the Appalachian Trail offers plenty of opportunities for scenic day hikes and overnight backcountry excursions. The route is a mix of lowlands and steep terrain, ascending to the state’s highest point (and incredible views) at Mt. Greylock. Don’t miss the natural history exhibits at the Mt. Greylock Visitor Center in Lanesborough. Weather permitting, if your legs are ready for the 89 steps to the top of the 92-foot Veterans War Memorial Tower at the summit you’ll be rewarded with spectacular views of five states. Mt. Greylock auto roads will reopen this spring. 

Natural Bridge State Park, North Adams

Discover North America’s only natural marble arch, a geologic wonder spanning a steep gorge carved by glacial erosion more than 13,000 years ago. The 48-acre Natural Bridge State Park is also home to an abandoned marble quarry that is an important part of the industrial history of the northern Berkshires. Open late May to mid-October.

A group hiking through shaded woodland on a walking path with greenery surrounding them

Berkshire Camino

Berkshire Camino

For a memorable experience that takes you inward as well as outdoors, book a private guided walking tour with Berkshire Camino. Route options include walkabouts to local cultural and historical sites as well as moderately paced scenic ridgeline hikes. All are designed with the casual hiker in mind. Seasonal, May to October.

Tamarack Hollow, Windsor

Explore flora, fauna, and foraging on a guided hike with naturalist Aimee Gelinas of Tamarack Hollow. In addition to teaching the wonders of nature, she also offers lessons in (and performs) West African and Caribbean drumming and song. Seasonal, reservations required.

Mount Greylock peeks out from green trees and tall grass at the South Meadow of Greylock Glen

Greylock Glen, Adams

In the Berkshires for hiking, biking, or ski touring? Head for Greylock Glen, where more than a thousand acres of woodlands, fields, streams, ponds make the perfect four-season playground. There’s even a waterfall. Stay tuned for details on the upcoming opening of the Greylock Glen Outdoor Center, Campground and Lodge.

Pleasant Valley Wildlife Sanctuary, Lenox & Richmond

There’s something magical about connecting with nature and Mass Audubon makes that experience accessible to all. The seven miles of marked trails and walkways at Pleasant Valley Wildlife Sanctuary bring you closer to Berkshire wildlife and their habitats, including birds and beavers. Enhance your visit with family-friendly educational programming and activities geared for explorers of all ages. Trails open daily, dawn to dusk.

A group hiking through a woodland trail in the spring

Photo Credit Christina Lane Photography

Also…Explore the NEW

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.

Whether you’re a beginner or a seasoned explorer, hiking trails in the Berkshires bring you closer to places you can only encounter while on foot. Many of them are also near a delicious meal and comfy lodging! Where will you venture next in the Berkshires?

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Cover photo: Ogden Gigli

Mount Greylock

Explore Things to Do

Our region is surrounded by picturesque mountains, lush green valleys, and crystal clear waters where you’ll find numerous, unique recreational activities all year long. Start planning your visit to the Berkshires today!

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