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The Best Hiking In Massachusetts: Our Favorites Hikes

With 90 miles of the Appalachian Trail traversing it, it’s no surprise that hiking in Massachusetts is a great way to experience its natural bounty. But the Appalachian Trail is far from the only hiking opportunity in the Bay State.

Read on for a look at popular Appalachian Trail hikes in Massachusetts and other hikes that display the state’s many delightful vistas.

Directional and Information Signas at the Beginning of a Mountain Trail

Best Hiking in Massachusetts: Appalachian Trail

Nearly any hiker will confess a desire to traverse the entire 2,175-mile length of the Appalachian Trail from Georgia to Maine. Most hikers, though, will manage to tackle only a few sections of the trail.

If you’d like to log some miles on the Appalachian Trail, Massachusetts offers lots of opportunities for day-hiking the iconic path. There are some difficult sections of the Appalachian Trail in Massachusetts, but the hikes listed here are rated easy or moderate.

Read on for a look at some of the best ways to experience the Appalachian Trail in Massachusetts.

Egremont, Massachusetts, USA A small valley draped in clouds after the rain.

Jug End Road to Mount Bushnell

Rated moderately challenging, this 3.6-mile out-and-back hike near the town of Egremont in southwestern Massachusetts is nonetheless a great day hike. Plan to spend a little more than two hours on the trail, with the reward of sweeping green vistas from atop Mount Bushnell.

You’ll certainly do some uphill work on this section of the Appalachian Trail, which includes an elevation change of 1,100 feet. You’ll likely have plenty of company during your hike, as Jug End Road to Mount Bushnell is popular with many runners.

You should plan on using trekking poles on this hike, due to the rocky nature of some parts of the walk. You’re welcome to bring your dog along, as long as he or she is leashed.

Goose Pond Road to US Highway 20

A little farther up the Appalachian Trail, near Becket and Tyringham, is the 4.5 mile section between Goose Pond Road and US Highway 20.

Taking this easy 9-mile out-and-back adventure includes the reward of seeing Upper Goose Pond, where you can watch anglers trying their luck. Or, you can sample the waters of Upper Goose Pond yourself, enjoying its status as an old-fashioned swimming hole.

Be aware, though, that there is no restroom or other place at the pond to change into a swimsuit, so plan accordingly. Camping is allowed on this part of the trail, but only at Upper Goose Pond Cabin.

Lee to Tyringham

If you’d like a bit more of a challenge for hiking the AT in Massachusetts, check out the 9.5 miles between Lee and Tyringham. Also featuring Upper Goose Pond, this route is rated moderately challenging.

You should plan on spending about 5 hours on the trail to complete this hike. There are some steep sections, particularly as you come into or leave Tyringham.

Best Hiking in Massachusetts: Eastern

When you’re talking about leisure time in eastern Massachusetts, you’re talking about seeing cities like Plymouth and Boston, or enjoying the Cape Cod seashore. But for hikers, whether novice or experienced, there are plenty of other ways to experience this part of the state.

Read on for a look at opportunities for hiking in Massachusetts centered around the eastern part of the state.

Two bicycles on the beach trail at sunny summer day in Cape Cod beach, Massachusetts.

Head of the Meadow Trail

Located between Truro and Provincetown within the Cape Cod National Seashore, the Head of the Meadow Trail is an easy 2-mile paved trail. Running between High Head Road and Head of the Meadow Beach, the trail is shared among pedestrians, bicyclists and skaters.

Of particular interest on this trail is the site of a freshwater spring — now dry — discovered by the Pilgrims in 1620. The location is identified with a historical marker set into a piece of granite.

At the end of the trail, you can enjoy Head of the Meadow Beach, although there is a charge for visiting the beach. There is a bathhouse on site for your convenience.

Getting to the trail for this experience in hiking in Massachusetts may be a bit of a challenge. High Head Road, which leads to the trail parking lot, is filled with potholes. So, be prepared for a bumpy and slow ride before your walk. Parking is limited to two hours.

Middlesex Fells Reservation

A short distance from Boston is Middlesex Fells Reservation, a 2,200-acre public recreation area. A perfect diversion from time in the city, Middlesex Fells Reservation — or, just “the Fells” — offers 100 miles of various mixed-use trails.

There is no camping at the Fells, so you’ll need to use it as a day trip to fulfill your hiking needs. If you’re interested in birdwatching, the 6-mile West Middlesex Fells Reservoir Trail will be a good bet for you. If you just want to stretch your legs a bit, try the 1.5-mile Cross Fells Trail to Spot Pond.

Other great hikes include the 4.2-mile East Middlesex Fells Reservation Loop Trail, featuring vistas of the Boston skyline. There’s also the 6.6-mile out-and-back Two Towers Trail, which features two observation towers for surveying the Fells and points beyond.

Bridle Trail

Located in the town of Marshfield on the South Shore, the Bridle Trail is a great example of hiking along old railroad beds in the state. The tree-lined 3-mile trail offers an interesting way to experience small-town life in Massachusetts.

Beginning in Marshfield’s Dandelion Park, the Bridle Trail ends amid an array of the town’s shops and restaurants. If you’re lucky, your visit to the Bridle Trail might coincide with some live music or other celebration to immerse yourself into the town.

Otherwise, nearby beaches can help round out your time enjoying the Bridle Trail.

Best Hiking in Massachusetts: Central

There are walks through history in the eastern part of Massachusetts, and the western part includes the Appalachian Trail. So it might be easy to conclude that hiking in Massachusetts doesn’t include the center of the state. Easy, but wrong.

Read on for a look at just a few of the hiking opportunities in central Massachusetts.

Tully Lake in Royalston, Massachusetts

Southern New England Trunkline Trail

Covering 22 miles from the Connecticut state line to the Franklin State Forest, the Southern New England Trunkline Trail (SNETT) passes through six cities. Those natural stopping points make the SNETT perfect for planning an out-and-back day hike or two or three.

Built on part of a former railroad right of way, the SNETT runs along a southern central border of Massachusetts. It includes the cities of Bellingham, Blackstone, Millville, Uxbridge and Douglas before ending in Thompson, Conn.

While the SNETT offers lots of scenic wonders, hikes should be aware that many parts of the route are unimproved. Also, there are a few breaks in the trail, and you’ll have to be careful navigating them to ensure you remain on the SNETT.

There are a number of places to access the SNETT where it crosses roads. Among the best places to access the trail are Grove Street in Franklin, Route 96 in Douglas, or Canal Street in Uxbridge.

Tully Trail

A 22-mile loop encircling the near-unspoiled Tully Valley near Royalston, the Tully Trail is a prime spot for hiking in Massachusetts. Camping is allowed, but only at designated locations along the trail.

Beginning at Tully Lake Campground, the Tully Trail almost immediately offers a mix of ridgeline views and waterfalls. Flat rock slabs along the trail offer perfect spots for relaxing picnic lunches.

The Tully Trail includes a winding route through densely forested land. It passes through parts of both the Royalston State Forest and the Warwick State Forest, including their wetland areas.

A shelter along the trail for camping, which can accommodate a dozen people or more, gets high marks from hikers who have used it.

Midstate Trail

Spanning 92 miles, the Midstate Trail offers some great hiking in Massachusetts, spanning from the Rhode Island border to the New Hampshire border. Located 45 miles west of Boston, the Midstate Trail is touted as an easy hiking opportunity that is also readily accessible.

Traversing forestland, historic sites and state parks, the Midstate Trail immerses hikers in the natural beauty of the state. It is possible to through-hike the entire 92-mile trail, with shelters along the way. However, through-hikers are advised to bring a tent for this foray into hiking in Massachusetts.

Long-distance hikers should also plan to stay in campgrounds, hostels or other accommodations near the trail rather than on the trail itself.

For day hikers, a 4-mile trek to the summit of Mount Watatic is recommended. More ambitious hikers might want to try an 11-mile out-and-back hike between Wallum Lake and the southern end of the Midstate Trail.

Best Hiking in Massachusetts: Western

Of course, the Appalachian Trail is always calling out to hikers in western Massachusetts. But the AT is not the only way to sample the natural attractions of the state. Read on to discover some of the other ways to enjoy a walk in the woods in the western reaches of the Bay State.

Rocky outcroppings on top of monument mountain in great barrington massachusetts on a sunny day.

Ashuwillticook Rail Trail

The Ashuwillticook Rail Trail, running 13 miles through Cheshire, Lanesborough and Adams, is one of the many abandoned railroad beds now used for hiking in Massachusetts. With views of the Cheshire Reservoir and Hoosic River, the trail is a great way to see area wildlife.

Open daily from dawn to dusk, the Ashuwillticook Rail Trail’s amenities include a visitor center and picnic areas. The trail’s paved and leveled surface makes it a perfect way to experience a mile or two, or even more, of Massachusetts.

The Ashuwillticook Rail Trail is a particular treat during the fall, when autumn foliage is in its full-colored spendor. In winter, the trail is an ideal venue for snowshoeing.

The trail crosses a number of roads on its route, so take extra care when moving through those areas.

Monument Mountain

Covering nearly 4 miles near Great Barrington, the Monument Mountain Summit Trail is a moderately difficult out-and-back route. Open year-round, this opportunity for hiking in Massachusetts is a particularly splendid walk in June, when mountain laurel and other wildflowers are in bloom.

Also along the trail, brooks and waterfalls abound as another visual treat from the natural world. From the top of Monument Mountain, hikers are rewarded with majestic views of the Housatonic River Valley.

The trail is open year-round from sunrise to sunset, with ample paid parking available.

Robert Frost Trail

Running for nearly 50 miles through the Connecticut River Valley, the Robert Frost Trail passes through nearly a dozen towns. Camping is not allowed along the trail, but with the numerous towns along its length, it’s perfect for single-day hiking in Massachusetts.

If you’d like to stay longer on the trail, check before you go for Airbnb or other short-term rental or lodging options.

The trail can be challenging, but hikers get a chance to see an array of natural vistas, from tranquil ponds to rugged rock faces. Some of the trail crosses private lands made available through easements or other arrangements, and hikers are advised to be very respectful of those areas.

Wrapping up the Best Hiking in Massachusetts: Our Favorite Hikes

After learning about all of the amazing opportunities for hiking in Massachusetts, you should be ready now to explore the state’s natural beauty on foot.

For more on enjoying nature in the Bay State, check out Beyond The Tent’s guide to the best camping spots in Massachusetts.