Massachusetts hiking: 5 trails you should try

Monument Mountain in Stockbridge provides beautiful views for hikers. (Getty Images)

If you’re into hiking, Massachusetts has a lot to offer.

If you’re close to Boston, the Blue Hills Reservation offers 125 miles of trails topping out at 635 feet in elevation.

But if you drive outside the 495 belt, there is some fantastic hiking in higher elevations that the Bay State offers.

So here’s a starter pack of trails for hikers who want to try some of the more challenging and scenic trails in Massachusetts.

MORE HIKING GUIDES: 5 hikes in New Hampshire | New England’s best hassle-free hikes | 5 great off-the-beaten-path hikes | 10 family-friendly hikes

1. Monument Mountain/Peeskawso Peak, Stockbridge

Difficulty: 4/5 | Trail info

Monument Mountain is the peak that Herman Melville and Nathaniel Hawthorne once hiked as they discussed the story that would one day become Moby Dick. Today, you can draw on the same inspiration as you climb this mountain that was once considered sacred by the Mohican tribe.

At 2.4 miles and with 669 feet of climbing, most of the difficulty of this loop comes from the multiple steep sections and intense rockiness at the top. Either bring your A-game or your high-top hiking shoes (or, preferably, both) to avoid ankle injuries.

You’ve got your choice of trails here: Peeskawso Peak, Mohican Monument, or Hickey Trail. From the top, you’ll have incredible views over southwestern Mass. and the Housatonic River. Bring your dogs, but they must be leashed.

2. Mount Watatic, Ashburnham

Difficulty: 3/5 | Trail info

Central Massachusetts occasionally gets overlooked in lieu of the more mountainous west, but Mount Watatic is proof that this region has some of the best hiking in the state. This 2.8-mile loop trail takes about an hour and a half for experienced hikers and climbs a total of 711 feet.

Expect some steep bits on the Wapack Trail, which means you’ll probably want to avoid this one when it’s icy or extremely wet. You can find the trailhead on Route 119 in Ashburnham. Though it’s a bidirectional loop, it’s more rewarding when hiked in the counterclockwise direction — that’s because the northern part of the Wapack Trail is less steep than the southern part.

Dogs are welcome but need to be leashed.

3. Mount Greylock via Bellows Pipe Trail, Adams

Difficulty: 5/5 | Trail info

Ascend to the top of Massachusetts’ highest peak, Mount Greylock, at 3,491 feet elevation. The Bellows Pipe Trail gets you there over the course of 6.5 miles and with 2,260 feet of climbing. The honest truth here is that a good chunk of this trail isn’t particularly exciting — it’s largely a steady climb up to the top.

But when you reach the top, it’s all worth it. You’ll have 360-degree views over mountains and lowlands, with some sightlines as far as 90 miles on a clear day. Stay the night in the Bascom Lodge if that’s your thing, or keep exploring via other trails like Pecks Falls, Deer Hill Falls, and others.

Dogs are welcome, and you can even enjoy some off-leash fun if they’re well behaved.

4. Mount Race/Mount Everett, Mount Washington

Difficulty: 5/5 | Trail info

This 7.6-mile out-and-back trail is perfect for anyone looking to gain some altitude on a half- to full-day hike. With 2,480 feet of climbing and waterfalls, multiple mountain summits, and lots of seclusion, this is a must-hike trail. And yes, “Mount Washington” is a town in the southwest corner of Massachusetts, not to be confused with the actual mountain in New Hampshire.

Start from the parking area and make your way up Race Brook trail. At the Appalachian Trail junction, head south and climb Mount Race; then head back north to summit Mount Everett before retracing your steps down Race Brook Trail. Rattlesnakes are not uncommon here, so keep your dogs on a leash.

5. Purgatory Chasm State Reservation, Sutton

Difficulty: 3/5 | Trail info

You can technically milk quite a few miles out of this little spot, but you’ll be less concerned with mileage than with climbing around on the incredible granite protruding out of the earth. Purgatory Chasm itself is a quarter-mile mile long and runs between solid granite walls that reach up to 70 feet high.

Rock climbers, picnickers, and hikers alike will almost certainly be sharing this space with you. Walk around and experience the beauty of this landmark, whether that’s hiking its many trails or bouldering on its natural rock walls. Dogs need to be on a leash here.