10 Best Hiking And Trekking Spots In Massachusetts, USA

hiking in massachusetts
| 6 min read

City life can sometimes get overwhelming, and a retreat to nature is just the thing to recharge and refresh yourself. If you would like to get in some exercise, breathe in the fresh air, and stretch your legs, why not consider choosing a hiking trail according to your fitness level and needs? One of the best things about being in the great state of Massachusetts is the proximity to many beautiful state parks and hiking trails. Plan ahead for your next free weekend and study this list of the best hiking and trekking spots in Massachusetts, USA!

1. Acorn Trail

Great Brook Farm State Park, Carlisle MA
Source: Photo by Wikimedia Commons user John Phelan used under CC BY-SA 4.0

Acorn Trail is a 4.8 km (3 mi) trail that is marked as an easy, beginner-friendly hiking trail. Located in the scenic Great Brook Farm State Park, it is a great place for families - and leashed pets - to spend a sunny day out in nature. This trail is mainly flat and offers peaceful views of the woodlands. After a one-hour or two-hour walk, visitors can relax on benches back at the Visitors’ Centre. The Great Brook Dairy Farm is also open to the public, with free tours on weekends. A popular choice of treats to have at the creamery is a graham cracker-flavoured ice cream topped with crunchy cereal.

Acorn Trail

Address: Great Brook Farm State Park, 165 North Road, Carlisle, MA 01741, USA

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2. Appalachian Trail

Appalachian Trail at Newfound Gap
Source: Photo by Wikimedia Commons user Blinutne used under CC BY-SA 3.0

The Appalachian National Scenic Trail, or Appalachian Trail, is the longest hiking path in the world. It stretches across the eastern region of the US, starting from Georgia in the south to Maine in the North. It cuts across 14 states and covers a total distance of over 3,500 km (2,174.7 mi). From Massachusetts, there are a couple of access points and trails: Warner Hill in Pittsfield for an easy walk with scenic views, the Ice Gulch in Great Barrington for a moderately challenging hike, and Gore Pond in Cheshire for seasoned hikers who want rewarding panoramic views from the summit. In an effort to protect and preserve the rich wildlife along the trail, visitors are encouraged to practise a “leave no trace” approach by camping only on marked areas, disposing of any waste responsibly, minimising the impact on natural landscapes, and respecting the wildlife.

Appalachian National Scenic Trail

Address: 649 Hartford Road, VT 05047, USA

Opening hours: 24 hours (daily)

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3. Cape Cod Rail Trail

Cape Cod Rail Trail 2014
Source: Photo by Wikimedia Commons user Kenneth C. Zirkel used under CC BY-SA 4.0

Cape Cod Rail Trail is an easy 41 km (25.4 mi) hiking trail that can be started and ended at any point due to its relative proximity to urban centres. Rest stops dot the trail and provide easy access to meals and even accommodation. One popular attraction to visit is Nickerson State Park, which offers views of spruce thickets, cedar groves, pine forests, and calm lakes. Cape Cod Rail Trail hugs the coast, and the beautiful blue waters of the ocean and bay can be seen as visitors walk along the mostly flat terrain. Visitors can also bring their swimming gear during the warmer months as a number of beaches can be accessed along the trail.

Cape Cod Rail Trail

Address: Route 134 (South Dennis) and Lecount Hollow Road between Kincaid St. and US 6 (Wellfleet), MA, USA

Opening hours: Sunrise - Sunset (daily)

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4. Skyline Loop Trail

Skyline Loop Trail is a 9.5-km (5.90-mi) moderate to difficult hiking trail that will take an average adult about six hours to complete. It is not recommended for younger children or those who are not in reasonably good physical condition. True to its name, Skyline Loop Trail can get quite steep, with a fairly challenging terrain of loose grit and pebbles, as well as some steep edges toward the end of the trail along the marked path. However, the trail does not disappoint with its stunning views of grasslands filled with wildflowers in spring and the snow-capped mountain in the distance. Some visitors have also reported sightings of wildlife like bears.

Skyline Loop Trail

Address: Blue Hills Reservation, Quincy, MA 02169, United States

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5. F. Gilbert Hills State Forest Loop Trail

F. Gilbert Hills State Forest Loop Trail is about 12 km (7.45 mi) long and is part of F. Gilbert State Forest. This trail has an even mix of easy, moderate, and challenging routes, making it suitable for everyone. The well-marked routes on the trails will bring visitors through peaceful stretches of woods and glimpses of the lake. Young children and leashed pets are welcome here, and there is plenty of shade along the trail for a rest before continuing. This spot also makes an excellent location for nature photography as the landscape changes according to the route and season, with waterfalls and marshlands being key attraction points on some routes.

F. Gilbert Hills State Forest Loop Trail

Address: 45 Mill St, Foxborough, MA, USA

Opening hours: 6:30am - 6:30pm (daily)

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6. Hoosac Range Trail

Hoosac Range Trail has a few paths that provide different experiences. 5 km (3.10 mi) from the start of the trail, along the ridge of Spruce Hill, hikers will be able to see Mt. Greylock, the highest point in the state of Massachusetts. From there, those who want to continue hiking should head to Mahican Mohawk Trail, originally used by Native Indian tribes in the region to traverse their territory. In total, this trail is about 10 km (6.21 mi) long and should take three hours for experienced hikers. For those who prefer to take a shorter and easier route, try the 2.6-km-long (1.61-mi) Sunset Rock Path with its spectacular view of the surrounding mountains. Do note that good hiking boots are a must as the steps and paths might be slippery with water or ice.

Hoosac Range Trail

Address: 2441 Mohawk Trail, North Adams, MA 01247, USA

Opening hours: 24 hours (daily)

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7. Borderland State Park Loop Trail

Borderland State Park Loop Trail is an unusual trail for hikers who are used to paths among the wilderness. This actually takes visitors past a historic mansion on the grounds of Borderland State Park. The mansion was formerly occupied by renowned botanist and orchid hunter Oakes Ames and his artist-inventor wife Blanche Ames. The trail is classified as easy for beginners and welcomes children and leashed pets. Pond Walk, the closest to the Visitors’ Centre and Ames Mansion, is 5 km (3.1 mi) long and can be completed in about an hour.

Borderland State Park Loop Trail

Address: 259 Massapoag Ave., North Easton, MA 02356, USA

Opening hours: 8am - 4pm (daily)

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8. Charley's Loop Trail

Purgatory chasm view 2
Source: Photo by Wikimedia Commons user Martinde used under CC BY-SA 3.0

Charley’s Loop Trail is a moderate to difficult hiking trail that takes visitors across Purgatory Chasm Park and covers a distance of about 3 km (1.86 mi). Known for its dramatic views of the granite ravine, which is carved out of ancient glaciers that now tower over hikers, the trail is hilly and requires some climbing. It is still considered fairly manageable for both new and experienced hikers since much of the trail is unpaved but flat. Its magnificent boulders will leave visitors awestruck. In warmer months, particularly during the spring and summer, the trail is teeming with an abundance of wildflowers, making for superb photography opportunities.

Charley's Loop Trail

Address: 198 Purgatory Road, Sutton, MA 01590, USA

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9. Ford's Folly Trail

In the early 20th century, automobile magnate Henry Ford came up with a plan to build a historic dam to store water from Nobscot Hill. In a nod to the area’s history, Ford decided to build the dam with traditional methods such as oxen and manpower. Perhaps because the project was carried out with no modern machinery, it was doomed from the start. Unfortunately, the dam was found to have been constructed on structurally unsound land, leading to it being left to sit dry. Today, visitors can walk over the dam itself and peer down at the old wreckage of cars at the bottom. This view has a decidedly less sinister cast to it though - the youth of the region apparently used to enjoy pushing cars that would otherwise be scrapped just to hear them crash.

Ford's Folly Trail

Address: 62 Bigelow Dr, Sudbury, MA 01776, USA

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10. Thunderbolt Trail

hiking in massachusetts | thunderbolt trail
Source: instagram

Thunderbolt Trail is one of the most challenging and fulfilling hiking trails in Massachusetts. With a total distance of about 8 km (4.97 mi), steep inclines, rugged terrains, and some unmarked trails, it will take most experienced hikers half a day at least to complete. However, the prize that awaits at the end of the trail is the summit of Mt. Greylock, the highest point in Massachusetts and also the first state park attraction here. Visitors must cross a mix of paths that range from flat land to dense forests and follow an unpaved trail to reach the Appalachian Trail leading to the top of the mountain. From there, you can visit the viewing observatory that offers an unparalleled, 360-degree view of the state and its surrounding sites. Try to spot North Adams, the Adirondack Mountain in New York, Green Mountain in Vermont, Mount Monadnock in New Hampshire, the Berkshires, Catskill Mountain in the Appalachian Range, and the Hudson River Valley.

Thunderbolt Trail

Address: Gould Road, Adams, MA 01220, USA

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Hiking and trekking for everyone

Whether you need a break from the hectic pace of city living or you want to explore the wild side by tackling some of the featured trails in this list, it is always a good idea to plan ahead and make sure that you are ready for the challenge. You can start off with the easier trails and then gradually work your way up to the more challenging ones. Be sure to give these suggestions a try whenever you find yourself in Massachusetts.

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Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Joyce is someone who currently combines the two great loves of her life by writing about travel and food. She is always on the lookout for new eateries to fall in love with and share about (albeit...Read more

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