18 Of The Best Hiking Trails In Massachusetts

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Although one of the smallest states in America, Massachusetts is the most populous state in the New England. Famous for its history, academia, and industry through its capital Boston, Massachusetts, it is also home to some world-class hiking trails!

Bordering the Atlantic Ocean, and with over sixty percent of the state covered with temperate deciduous forest, which is home to a menagerie of wildlife, Massachusetts hosts various biomes for keen hikers to explore. Especially those looking to brave the more mountainous terrains! 

With literally hundreds of hiking trails to explore, it can be difficult to narrow the various trails down to a single list. However, the following eighteen trails are some prime examples of the hikes and locations available to novice and experienced hikers!

1. Ipswich River Wildlife Sanctuary Trails

Located in Topsfield, this Wildlife Sanctuary is host to over twelve miles of hiking trails to explore, dotted around this vast tract of wilderness.

Although this may seem daunting to novice hikers, rest assured that the majority of the trial in this sanctuary is very well maintained with low elevations, meaning that a number of the trails amount to little more than a lengthy walk.

However, while some of the trails, such as the Rockery Trail, are best suited for families and novice hikers, there is enough variety in the sanctuary to provide more experience hikers with a bit of a challenge!

For fans of wildlife, this is a must-visit location to experience the biodiversity of Massachusetts’ fauna and flora, with common sightings of river otters, turtles, deer, and various wetlands birds.

Finally, summertime provides ample opportunities for water activities, including but not limited to swimming, kayaking, and canoeing. 

2. The Skyline Trail Loop

Located in the Middlesex Fells Reservation, The Skyline Trail Loop is a pretty challenging hike and will take most hikers between four and six hours to complete the nine-mile trek through the unspoiled landscape. 

This is because the trail involves a lot of elevation from start to finish as you make your way up Hancock Hill via a series of stone steps and the final climb up the Eliot Observation Tower.

The reward, other than some much-needed outdoor exercise, is unparalleled views of the Boston skyline, while further stops along the way include the great Blue Hill Summit and the Blue Hill Meteorological Observatory.

3. Purgatory Chasm Trails

Situated in the Purgatory Chasm Reservation, these popular hiking trails are known for their caves, rock formations, and 70-foot granite walls. Consequently, there are many stops and sites to explore, such as The Corn Crib, The Coffin, and Lover’s Leap.

While there are a few hikes to participate in, two of the best and easiest hikes include the Purgatory Chasm Loop and Purgatory Brook Trail, both of which can be scoped out on downloadable maps via advance the park’s official website.

4. Mount Greylock State Reservation Trails

As the highest point in Massachusetts, Mount Greylock is host to numerous challenging trails that sport uneven rocky terrain and high elevation levels.

For experienced hikers, the Bellows Pipe and Thunderbolt trail are some of the most challenging hikes in the area, with significant elevation. In contrast, the Chesire Harbour Trail is a bit less challenging due to increased elevation, although it’s a bit longer than the aforementioned trails.

Despite the challenge, the peak of Mount Greylock sits at 3 491 feet, offering sweeping views of the surrounding five states. This peak can also be accessed via a road that follows two further stops: the Bascom Lodge and the War Memorial Tower.

5. Robert Frost Trail

Traversing large sections of the Massachusetts wilderness, we have the Robert Frost Trail, which sports over 47 miles of winding paths that splinter off into other well-known hikes throughout the state.

Although the trail can be completed in its entirety, which means it will take most hikers a few days, making it the perfect hike/camping combination, less intrepid hikers can opt to go on and off the trail whenever they want! 

Although the trail mostly takes hikers across the length and breadth of the New England woods, it ends with a fire tower right at the top of Mount Toby, rewarding the bravest of hikers with sweeping vistas of the surrounding forests!

As the most versatile and customizable of all hikes on this list, the Robert Frost Trail is perfect for hikers/campers of all experience levels!

6. Mount Norwottuck And Horse Caves Trails

Situated in Mount Holyoke Range State Park in west-central Massachusetts, this park offers numerous trails, all of which are accessible online or in person at the visitors center.

At just over three miles with an elevation of 1 100 feet, the Mount Norwottuck hike is a fairly challenging hike that takes hikers up to the summit of Mount Norwottuck, where they will be treated with views of the surrounding Connecticut River Valley.

On the return trip from Mount Norwottuck, make sure to take a slight detour should you feel up to it to explore the Horse Caves. While more overhangs than actual caves, the Horse Caves are historical landmarks, having been bases for rebels during the Shay’s Rebellion.

7. The Freedom Trail

Situated in the Greater Boston area, the Freedom Trail is a leisurely 2.5 mile that takes you through Boston’s historic downtown to explore the sites of one of America’s most historical cities.

Some key sites include but are not limited to: the starting location of the Boston Massacre, Paul Revere House, Faneuil Hall, the battleship “Old Ironsides”, and Bunker Hill.

Whether you decide to take a guided tour or simply opt to follow the yellow bricks that mark the trail, this is a must-see for new visitors to Boston and history buffs alike! 

8. Bish Bash Falls Trail

Situated in the Bish Bash Falls State Park in the southwest of Massachusetts and straddling the New York state line, you will find Bish Bash Falls, the largest waterfall in the state.

While the hike itself is a fairly short walk at 2 miles through trees and rocky paths that regularly intersect with babbling brooks that feed into the Bish Bash Falls, the reward at the end of the approximate 45 minutes of hiking is the site of a 60-foot waterfall at the end of your journey!

9. Harrington Trail

Situated in central Massachusetts, this moderate 3-mile hike takes you to the summit of Mount Wachusett.

While the hike begins with a trail through lush forests, the increased elevation toward Mount Wachusett can prove challenging for some hiking, so make sure to equip a good pair of hiking boots!

Finally, since the trail begins in the town of Princeton, make sure to visit some of the local spots before or after your hiking. A popular spot is the Mountain Barn, which offers a wide array of craft beers and meals for its patrons.

10. Salem Heritage Trail

Situated in the town of Salem, which played host to the infamous Salem Witch trials, the Salem Heritage Trail allows visitors to have either a guided tour or a solo expedition at the scene of one of Massachusetts’ grisliest and spookiest times in history!

An easy walk through the town of Salem allows yourself and the whole family to explore the Witch Museum, the Broad Street Cemetery, the Witch House, and the aptly named Gallows Hill (if you dare!)

11. Racebrook Falls And Mount Everett Trails

Situated at Mount Everett, these trails are some of the most challenging on this list, despite their relatively short length of approximately six miles.

Although these trails should be experienced only by experienced hikers, there are ample spots during the hike to stop and rest, many of which feature waterfalls, lush forest foliage, and sweeping mountain vistas.

12. Cape Cod Rail Trail

Situated in and around Nickerson State Park, the Cape Cod Rail Trail is a multi-purpose paved trail that runs for approximately 22 miles through forests, cranberry bogs, and sandy ponds.

Given that the trail is designed for cyclists in mind and runs from Dennis, through the Nickerson State Park, into Orleans, and onward across the Cape Cod National Seashore all the way to the South Wellfleet, there are various paths in which to start and finish one’s hike.

A recommended trail that promises a day out through beautiful scenery, with low elevation, would be the 11 miles beginning at the Nickerson State Park and ending at the National Seashore. 

13. Appalachian Trail

Spanning thousands of miles, the world-famous Appalachian Trail crosses over 14 states; however, some of the best parts of the trail would be seen to run through western Massachusetts.

Although you can begin and end your journey just about anywhere on the Appalachian Trail, seasoned hikers and campers should opt to take on the New England section that will take them through Mount Greylock Park, Clarksburg Forest, Goose Pond, and Mount Wilcox.

Just make sure to pack ample food, water, camping equipment, and a variety of clothing, so you are prepared for all seasons and weather conditions! 

14. Martha’s Vineyard Trails

Situated in Martha’s Vineyard, an island off the southeast coast of Massachusetts, this picturesque island is host to numerous hiking trails across the length and breadth of the island.

For those looking for slightly more challenging hikes with elevation for sweeping views of the island, makes sure to explore the Menemsha Hill Trails and the Great Rock Bight Preserve Trails. 

15. Monument Mountain and Peeskawso Peak Trail

As the birthplace of one of America’s well-known pieces of literature, Moby Dick, given that this was a favorite hiking spot for authors Nathaniel Hawthorne and Herman Melville, Monument Mountain is both a location for history and scenic views.

Hiking trails around Monument Mountain include the aforementioned Peeskawso Peak Trail and the Hickey and Mohican Mountain Loops, all of which are fairly short hikes at 2.5 miles but challenging due to their elevation and uneven ground.

Well marked, maintained, and easy to navigate, although difficult to traverse, these hiking trails offer views of some of the best rock formations in the state of Massachusetts.  

16. World’s End Trail

Situated at the Boston Harbor Islands National Park, the World’s End Trail is a popular hiking destination for Bostonians looking to escape the hustle and bustle of the city.

Originally designed as carriageways by Frederick Olmsted in 1890, these sweeping pathways are very well maintained and extend for approximately 3.8 miles above the city of Boston, Boston harbor, and the surrounding marshlands.

With various spots to stop and have a picnic, as well as common sightings of wildlife such as turkeys, chipmunks, and deer, The World’s End is a great way to spend a day out in nature with friends and family!

17. Walden Pond Trail

Situated at the Walden Pond State Reservation, the Walden Pond Trail is a short 1.7-mile loop that includes some elevation with hills and stairs along fenced-off slopes across the reservation.

The lake itself has a sandy beach, making it a popular spot for swimmers, canoeists, and bathers looking for a casual picnic spot.

However, should the beach not be your idea of a day out, slight deviations toward the Walden Woods offer further hiking trails and lush forests for adventurous hikers to explore! 

18. Halibut Point Trail

Located within Halibut Point State Park, the Halibut Point Trail is an easy 1.6-mile hike that offers views of Babson Farm Quarry, the Atlantic Ocean, and Mount Agamenticus in the neighboring state of Maine.

While a bit rocky, the trail is relatively easy, with some slight elevation. Making it the perfect trail for those looking for some picnic spots or open spaces to walk their dogs!


As can be seen above, Massachusetts is an excellent hiking location for anyone willing to take the time to explore some of the multiple opportunities this diverse state has to offer!