Best Hiking In Massachusetts: Top Trails in the Bay State

Want to learn more about the best hiking in Massachusetts but don’t know where to start? Our list of the 13 top trails and mountains to hike in MA is what you need.

Gaby Pilson
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The 13 Best Hikes In Massachusetts

Looking to hike Massachusetts?

You’re in the right place! In this guide, we will be covering the following:

    • What are the 12 best hikes in Massachusetts
    • Key travel information to get you to the trailhead
    • What you can expect when hiking in MA
    • Which trails are right for your preferred hiking style

Want to learn more about the best hiking in Massachusetts but don’t know where to start? Our list of the 13 top trails and mountains to hike in MA is what you need.

Known for its stunning coastline and rugged trails, Massachusetts is a true hiker’s paradise. In fact, planning a hiking trip to the Bay State can be a challenge because there are hundreds of great trails to explore.

If you want to get out and explore the wonders of Massachusetts, have no fear—we’re here to help. Up next, we’ll introduce you to 13 of the best hiking trails in Massachusetts. That way, you can find the perfect hike for your next trip to the Bay State.

The 13 Top Massachusetts Hiking Trails

1. Peabody Loop, Noanet Woodlands

Peabody Loop, Noanet Woodlands
Photo by Mike Halsall / CC BY-ND 2.0
  • Trail type: Loop
  • Length: 2.6 miles (141ft ascent)
  • Difficulty: Easy
  • Access: Noanet Woodlands Parking Lot on Powissett Street near Dover

A mere 30 minutes from downtown Boston, Noanet Woodlands is the perfect escape from the hustle and bustle of the big city.

Inside this stunning forest preserve, you have access to a 16-mile-long network of trails. Although all the trails make for a great wonder in the woods, the Peabody Loop is a fantastic afternoon adventure.

To access the Peabody Loop, you’ll start at the Powissett Street trailhead and follow the blue blazes. Along the way, you’ll enjoy pristine woodlands, chirping birds, and views of glistening ponds.

If you’re short on time, you can stick to the Peabody Loop and follow the path back to the parking area. Or, for more of a workout, you can hop on the path to nearby Noanet Peak. From the summit of the peak, you can even see the Boston Skyline in the distance. What could be better?

2. Mount Greylock Loop, Mount Greylock State Reservation

Mount Greylock Loop, Mount Greylock State Reservation
  • Trail type: Loop
  • Length: 6.6 miles (2,226ft ascent)
  • Difficulty: Moderate to hard
  • Access: Bellows Pipe Trailhead on Gould Road near Adams

The tallest peak in all of Massachusetts, Mount Greylock is a must-do for serious adventurers. Located in the northwest corner of MA, there are many paths to the summit of Greylock. However, this loop allows you to experience as much of the peak as possible for the full hiking experience.

To access Mount Greylock, start at the parking area on Gould Road near the town of Adams. Be warned, however, that the parking area is near private property. So, be sure to park in the designated lot to avoid any access issues.

For this 6.6-mile hike, you’ll first make your way up the Bellows Pipe Trail. This path is well-marked and even overlaps with the Appalachian Trail (AT) for a short section. You’ll climb switchbacks for quite a while before topping out on the summit of Mount Greylock.

Once on the summit, you can sit back and enjoy the amazing views over Western Mass. After you’ve enjoyed the vistas, follow the AT south for a short time until you hit the Gould Trail. This path will take you down toward a small parking area that’s just a short walk down the road from your original starting point.

3. The Great Island Trail, Cape Cod National Seashore

The Great Island Trail, Cape Cod National Seashore
  • Trail type: Loop
  • Length: 8.8 miles (132ft ascent)
  • Difficulty: Moderate to hard
  • Access: Great Island Parking Area near Wellfleet

One of Massachusetts’ premier seaside hikes, the Great Island Trail is the perfect summer activity. 

From the trailhead at Wellfleet, you have a choice of 4 different destinations on this hike: Jeremy Point, Jeremy Point Overlook, Great Beach Hill, and Great Island Tavern.

To visit all 4 points of interest, you’ll venture out on an 8.8-mile hike across sandy beaches and grassy plains. Along the way, you’ll be treated to unparalleled vistas of Cape Cod and the Atlantic Ocean.

Nevertheless, it’s important to note that a decent portion of this path is actually a sandbar. That means parts of the hike are submerged during high water, making travel difficult, if not impossible, at high tide.

So, if you want to hike all the way out to Jeremy Point, check the tide tables before you head to the park. You can always ask for tide information at the Cape Cod National Seashore Visitor Center before starting your journey, just to play it safe.

4. Mount Watatic and Nutting Hill Loop, Watatic Mountain State Wildlife Area

Mount Watatic And Nutting Hill Loop, Watatic Mountain State Wildlife Area
  • Trail type: Loop
  • Length: 2.8 miles (644ft ascent)
  • Difficulty: Moderate
  • Access: Parking area on Rindge State Road near Ashburnham

Nestled along the Massachusetts-Connecticut border, this short peak ascent of Mount Watatic is an exceptional day hike.

To access this hike, you’ll start at a small trailhead at the southern end of the Watatic Mountain State Wildlife Area. From the parking area, you’ll head off on a rocky trail with a few minor stream crossings in the first quarter-mile.

After navigating the creeks, you’ll start climbing upward until you arrive at your first destination: the summit of Mount Watatic. Once you get your fill of the beautiful views, you can descend down a mellow little path on the northwest side of the peak.

Eventually, the route will start to climb again, leading you to the summit of yet another high point. This time, you’ll stand atop Nutting Hill, which is a nice rest area, albeit with fewer views than its taller neighbor.

As soon as you get a chance to catch your breath, you can head down the hill and loop back around to the parking area. Overall, this hike is short, sweet, and well worth the effort if you’re looking for a fun day hike in southern MA.

5. Walden Pond Hiking Trail, Walden Pond State Reservation

Walden Pond Hiking Trail, Walden Pond State Reservation
  • Trail type: Loop
  • Length: 1.8 miles (44ft ascent)
  • Difficulty: Easy
  • Access: Parking area off of Route 126 near Lincoln

One of the most historic hiking trails in all of MA, the trek around Walden Pond is an excellent option for history buffs and naturalists everywhere.

Departing from the small parking area at the southeastern corner of the state park, this casual walk is great for the whole family. It follows a relatively flat and wide path around Walden Pond, with lush forests and plenty of wildlife.

The highlight of this hike, however, is easily Henry David Thoreau’s cabin site. Although Thoreau’s original cabin (of Walden; or, Life in the Woods fame) is no longer there, you can see a replica of his home on this hike.

Plus, if you’re visiting in the summer months, don’t forget to bring your swimsuit! There are some great swimming beaches on Walden Pond, which make for an excellent way to cool off in the summer heat.

6. Bash Bish Falls Hike, Bash Bish Falls State Park

_Bash Bish Falls
  • Trail type: Out-and-back
  • Length: 1 mile (346ft)
  • Difficulty: Easy to moderate
  • Access: Parking area on Falls Road near the town of Mount Washington

Massachusetts’ tallest waterfall, Bash Bish Falls is a popular family-friendly hike for summertime adventures. Interestingly, the falls can be accessed from either the New York or the Massachusetts side of the border, though we’ll discuss the MA hike here.

The hike starts out at a small parking area on Falls Road. Immediately after leaving the parking area, you’ll pick up a fairly wide path that heads directly into the woods.

Over the course of this short, yet mildly steep hike, you’ll climb up a short hill to a viewing area. From here, you can walk up to the banks of Bash Bish Brook, where you can gaze up at the magnificent falls.

That being said, it’s worth mentioning that the path can be very icy in the winter months. So, this hike is best during the early summer, when the falls are flowing at their highest levels. Alternatively, the falls are well worth visiting in the autumn when the fall foliage adds lovely colors to the landscape.

7. Skyline Loop, Blue Hills Reservation

Skyline Loop, Blue Hills Reservation
  • Trail type: Loop
  • Length: 3 miles (1,100ft ascent)
  • Difficulty: Moderate
  • Access: Reservation Headquarters parking area near Milton

Perhaps the most scenic Boston-area hike, the Skyline Loop is undoubtedly one of the best hikes in Massachusetts. Offering scenery that rivals that of the White Mountains in New Hampshire, this hike offers a chance to summit Great Blue Hill—one of the tallest peaks on the Atlantic Seaboard.

To start this hike, park at the Blue Hills Reservation headquarters near the town of Milton. From there, you’ll follow a blue-blazed path that meanders its way up and down the Blue Hills.

Along the way, you’ll get to tag 5 separate high points, including Great Blue Hill. From the summit of Great Blue, you can even see the Boston Skyline in the distance. Once you get your fill of the exceptional views, continue down the path until you return to the parking area. 

Alternatively, if you want more of a workout, you can make a quick side trip to Buck Hill. Although Buck Hill is relatively short, it provides particularly good vistas of the Greater Boston Area. So, it’s well worth the visit!

8. Harrington Trail, Mount Wachusett State Reservation

Harrington Trail, Mount Wachusett State Reservation
  • Trail type: Out-and-back
  • Length: 2.5 miles (746ft ascent)
  • Difficulty: Easy
  • Access: Harrington Trailhead on Westminster Road near Princeton

Situated in the heart of central MA, the Mount Wachusett Reservation is a superb destination for a day of adventure. The Harrington Trail offers unparalleled access to the reservation, as well as a chance to summit its highest peak: Mount Wachusett.

After parking your vehicle at the trailhead on Westminster Road, you’ll start walking through a lush forest. The trail climbs slowly but surely upward as you make your way toward Wachusett’s summit. 

The path itself is actually quite wide, though it’s particularly rocky. As a result, proper footwear and even trekking poles are highly recommended. 

Once you are near the summit, you’ll need to do a bit of scrambling to reach the viewing area. However, at the top of Mount Wachusett, you’re treated to 360º views of Boston and even Mount Monadnock all the way in New Hampshire to the north.

Plus, if you’re keen on more adventure, you’ll be happy to know that the state park has a large network of trails to choose from. For added fun, you can even descend Wachusett via the Jack Frost Trail and create a mini loop back to the parking area.

9. Atlantic White Cedar Swamp Trail, Douglas State Forest

Atlantic White Cedar Swamp Trail, Douglas State Forest
  • Trail type: Loop
  • Length: 0.5 miles (30ft)
  • Difficulty: Easy
  • Access: Parking area on Wallum Lake Road near Douglas

One of the more unique hiking trails in Massachusetts, the Atlantic White Cedar Swamp is a must-visit for nature-lovers. This family-friendly hike offers a chance to experience one of the Bay State’s last remaining cedar swamps on a casual walk for all to enjoy.

You can access the hike from the parking area on Wallum Lake Road, which is well-signed and fairly easy to find. From the trailhead, you’ll follow a narrow, mostly flat boardwalk path through the swamp that’s perfect for kids and adults alike.

The path also has several numbered markers along the way. These numbered markers correspond to educational content in the state forest’s informational brochure, which you can pick up at the trailhead to learn more about the now-rare cedar swamp ecosystem.

10. Mount Race & Mount Everett via Race Brook Falls, Mount Everett State Reservation

Mount Race & Mount Everett Via Race Brook Falls, Mount Everett State Reservation
  • Trail type: Out-and-back
  • Length: 7 miles (2,700ft ascent)
  • Difficulty: Hard
  • Access: Race Brook Falls parking area on Route 41 near the town of Mount Washington

If you’re keen to hike a section of the Appalachian Trail (AT) in Massachusetts, this trek to Mount Rance and Mount Everett is a sure bet. Located in the heart of Mount Everett Reservation, this challenging adventure offers excellent views for your efforts.

To access this trek, you’ll begin at the Race Brook Falls parking area. You’ll start climbing uphill right out of the gate as you enter into a stunningly lush forest. This early part of the trek can get very steep, however, so be sure to wear proper footwear.

After navigating some steep sections of the path, you’ll be at the base of the three-tiered Race Brook Falls. Once you snap some photos of these gorgeous falls, you can head up the trail where you’ll find yourself in a saddle where you can stop for a quick break on the AT. At this saddle, you have the option between heading north to Mount Everett or south to Mount Race.

While either peak is a worthy destination, tagging both summits offers the best chance for panoramic views. Then, you can either retrace your steps and head back to the trailhead or you can follow the AT in either direction for more adventure.

11. Lynn Woods Loop, Lynn Woods Reservation

Lynn Woods Loop, Lynn Woods Reservation
Photo by thepiper351 / CC BY-SA 2.0
  • Trail type: Loop
  • Length: 7 miles (543ft ascent)
  • Difficulty: Moderate
  • Access: Parking area on Great Woods Road near Lynn

Located on the shores of Massachusetts Bay, Lynn Woods is the ideal escape from the hectic streets of Boston. The reservation offers nearly 30 miles of hiking trails, though this 7-mile loop allows you to see as much of the area as possible.

The best place to start your hike in Lynn Woods is from the large parking area on Great Woods Road. From there, you have access to nearly all of the paths in the reservation, including the large fire road that leads into the heart of the woodlands.

After ambling down the fire road for a few miles, you can turn onto Pennybrook Road (actually a trail, not a road), and then Walden Pond Road. The path will climb gradually until you reach the Mount Moriah Path. Then, you’ll ascend to the summit of Mount Moriah before descending down the other side.

Eventually, the path will hook back around and take you to a stone tower, which is worth checking out. At the tower, you can get even views of the Boston skyline as a reward for all your hiking before you head back to the parking area.

12. Mount Toby Trail, Mount Toby State Forest

Mount Toby Trail, Mount Toby State Forest
Photo by prettytypewriters / CC BY-ND 2.0
  • Trail type: Loop
  • Length: 3 miles (876ft ascent)
  • Difficulty: Moderate
  • Access: Mount Toby Trailhead on Route 63 near Sunderland

If you’re visiting central Massachusetts, the Mount Toby Trail is one you won’t want to miss. The highlight of the Mount Toby State Forest, this hike begins on Route 63 near Sunderland and summits the beautiful Mount Toby. 

To follow the loop, you’ll start in a counter-clockwise direction and ascend the steep, but steady Blue Trail to the summit. At the summit of Mount Toby, you can sit back and appreciate the marvelous views over the surrounding area. 

Once you’re ready, you can descend the Robert Frost Trail back down to the valley floor for a longer, but easier descent. Alternatively, you can return down the steeper Blue Trail, but this isn’t encouraged, especially during the icy winter months. 

That said, if you take the Robert Frost Trail, you also get a chance to climb up a small observation tower. This tower is highly recommended if you have a good weather day as the views are hard to beat. The tower also has some picnic tables, so don’t forget to pack a snack to enjoy along with the scenery!

13. Halibut Point Trail, Halibut Point State Park

Halibut Point Trail, Halibut Point State Park
  • Trail type: Loop
  • Length: 1.1 miles (50ft ascent)
  • Difficulty: Easy
  • Access: Parking area on Gott Avenue at Halibut Point State Park near Rockport

An educational experience that the whole family can enjoy, the Halibut Point Trail is one of Northern MA’s finest day trips.

You’ll access this enjoyable little hike from the parking area on Gott Avenue. Once you start walking, you’ll follow the trail toward an old quarry and fire tower, which is where the fun begins.

Toward the midpoint of the loop, you’ll be treated to expansive views of the entire Cape Ann coastline. Plus, if you follow a short spur trail toward the beach on a sunny day, you’ll even get a chance to see Mount Agamenticus some 80 miles away in Maine!

The Best Hiking In Massachusetts: New England’s Top Trails

Boasting everything from rocky summits to sunny beaches, the Bay State is a true outdoor lover’s paradise.

We hope that our list of the top hikes in Massachusetts helped you find your next outing. If you enjoyed our article, let us know in the comments below—we’d love to hear about your adventures.

Oh, and don’t forget to share our list with your friends so they can enjoy these amazing trails, too! See you in MA!

Gaby Pilson

Gaby is a professional polar guide, wilderness medicine instructor, and freelance writer with a master’s degree in outdoor education. She splits her time between the northern and southern hemispheres, chasing the midnight sun and helping others get outside to experience some of the world’s most beautiful places.

As an outdoor educator, Gaby is passionate about making the outdoors as accessible as possible for anyone looking to get into the mountains or out on the water. She is a certified Polar Guide, an AMGA Climbing Wall Instructor Course Provider, a NOLS instructor, and an accomplished climbing guide with a penchant for telemark skiing.

When she’s not hanging out with penguins in Antarctica or scouting for polar bears in the Arctic, you can find Gaby backpacking in Wyoming’s Wind River Range or drinking debatably excessive amounts of espresso and reading French existentialism in a quirky café.

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