From the woodsy hills of the Berkshires to the stunning heights of Mt Greylock, Massachusetts offers a handful of challenging and relaxation-focused hikes that allow you to explore the state’s natural beauty. Here are seven of our favorites.

Editor’s note: Please check the latest travel restrictions before planning any trip and always follow government advice.

Bash Bish Falls

In the very southwest corner of the state near the New York state line is Bash Bish Falls, the largest waterfall in Massachusetts. The water feeding the falls cascades down a series of gorges before splitting in two by a massive boulder perched directly above a picturesque pool. The falls drop as a stunning double waterfall, reaching heights of 60 feet, making it a popular site for landscape painters.

A short, steep trail leads directly to the viewing area from the Massachusetts parking lot. Alternatively, for a gentler walk, continue driving 1 mile west across the state border to the New York parking lot, where a more level path takes you to a scenic overlook. Although access to the pool at the bottom of the falls is currently closed to visitors, hikes from both starting points take approximately 20 minutes each way.

To reach Bash Bish Falls from Great Barrington, take MA 23 west to South Egremont. Turn onto MA 41 south and take an immediate right onto Mt Washington Rd (which becomes East St). Continue for 7.5 miles, turn right onto Cross Rd, then right onto West St. After continuing for 1 mile, turn left onto Falls Rd and follow it for 1.5 miles. The parking lot and trailhead will be on your left.

Monument Mountain and Peeskawso Peak

Monument Mountain is a historically significant area in Massachusetts. Many fans of American literature know that Nathaniel Hawthorne and Herman Melville hiked this mountain and spent a day discussing what would later become Moby Dick. Pittsfield, Massachusetts, still hosts public readings of the classic novel and an annual hike to commemorate the authors’ collaboration.

Before Melville’s time, the mountain’s sister summit was known as Squaw Mountain, a name derived from a local legend about a Mohican woman. In 2021, local indigenous tribes and leaders renamed it Peeskawso Peak, replacing the outdated term with a name that means “virtuous woman” in Mohican. This change reflects a broader initiative to promote awareness of the region’s rich Indigenous history through trail signage and museum exhibits.

You can visit Monument Mountain and Peeskawso Peak just 5 miles north of Great Barrington center on US 7. From the parking lot, the 3-mile circuit ascends sharply via the Hickey trail, running along the cliff edge to Peeskawso Peak and the Devil’s Pulpit lookout. The view from the summit includes breathtaking vistas all the way to Mt Greylock to the northwest and the Catskills in New York.

Cape Cod Rail Trail

As the premier bicycle trail in Cape Cod, the Cape Cod Rail Trail spans 22 beautiful paved miles through forests, past cranberry bogs, and along sandy ponds perfect for a refreshing dip. This rural route, once a railroad line, stands as one of the finest bike trails in all of New England.

The trail begins in Dennis on MA 134, continuing through Nickerson State Park in Brewster, into Orleans, and across the Cape Cod National Seashore, all the way to South Wellfleet.

Along the way, you will encounter scenic views reminiscent of Old Cape Cod. There are opportunities to explore charming villages for lunch or sightseeing. If you’re short on time, consider starting at Nickerson State Park and heading toward the National Seashore for the most stunning scenery.

Bicycle rentals are available at trailheads in Dennis and Wellfleet, as well as near the National Seashore’s visitor center in Eastham. Free car parking is accessible at all four locations, except for Nickerson State Park.

The Blue Hills Reservation

Located just twenty minutes outside Boston, the Blue Hills Reservation offers over a hundred miles of trails, including one that provides panoramic views of the city from the summit of Great Blue Hill. The Skyline Loop Trail is a three-mile trek from the Blue Hills Reservation headquarters, featuring some challenging climbs, particularly as you tackle Hancock Hill via stone steps. Do not miss climbing the Eliot Observation Tower at the summit for the best views of Boston’s skyline.

Mt Greylock Trails

Mt Greylock caters to hikers of all skill levels, offering 45 miles of hiking trails across 13 marked routes, including a section of the Appalachian Trail. Frequent pull-overs along the access road allow hikers to explore the area’s scenic beauty, including waterfalls, before reaching the summit. Although the road to the top is closed from November to late May, the hiking trails remain open year-round.

Mount Norwottuck

Mount Norwottuck stands as the highest peak in the Holyokes, a unique mountain range formed from ancient volcanic basalt that runs east to west. The summit provides stunning views of the surrounding valley, and the trailhead near the Visitor’s Center is easily accessible from Amherst. You can reach Norwottuck’s peak (1,106 ft) via a moderate three-mile loop by combining the Robert Frost and Metacomet-Monadnock trails. Along the way, look out for a series of overhanging ledges known as the Horse Caves, which hold significance from early American history when insurrectionists sought refuge here after Shay’s Rebellion in the late 1780s.

Bartholomew’s Cobble

Located south of Great Barrington, Bartholomew’s Cobble is an excellent spot to spend a few hours. This 329-acre area features a “cobble,” which is a high, rocky outcrop of limestone, marble, or quartzite. With five miles of hiking trails, visitors can explore the cobble and the surrounding woods, including the challenging climb to Hurlburt’s Hill and the Ledges Trail that meanders along the Housatonic River.

Tyringham Cobble

For a delightful experience of this tiny village’s pastoral scenery, take a 2-mile hike over the undulating terrain of Tyringham Cobble, showcasing wildflower-strewn hillsides and breathtaking vistas. Be on the lookout for wild berries in the meadows and the uniquely shaped Rabbit Rock along this scenic Berkshires trail.

Dune Shacks Trail

Travel along MA 6 and, after a brief walk, you will enter a landscape of expansive dunes. Since there is no designated trail, you can wander freely through the sand hills, leading you to a lovely beach. Ensure you bring ample sunscreen and remember the starting point of your walk.

Only a few parking spots are available along MA 6, making it accessible by bike (though there is no bike rack) or via a rather long walk from town.

Hoosac Range Trail

Located near North Adams, an easy 1.6-mile trail leads to Sunset Rock, an excellent spot for blueberry picking during the season. If time permits, venture onto the moderate 6.2-mile trail to Spruce Hill, where hikers are rewarded with sweeping ledges and spectacular views. This trail is well-known for its rocky glacial cliffs and striking tree formations shaped by the wind and ice.

This article was first published Nov 2, 2020, and updated Apr 13, 2021.