Climbing & Hiking Trails - 14 min read

20 Best Hiking Trails in Massachusetts (Accessible to All!)

Alaina Johnson

Alaina Johnson, Updated November 2, 2022

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Massachusetts is not only home to one of the most prestigious universities, Harvard, but it also hosts a diverse array of hiking trails. When residents are looking to escape the hustle and bustle of the city, they have some great options available. During the fall, the leaves change to vivid orange and red hues that are worthy of anyone’s Instagram.

The state offers several prime hiking destinations, such as the Blue Hills Reservation and Mount Greylock State Reservation. You can pay a nominal day pass fee and spend hours exploring the scenic land and enjoying a picnic lunch. Many of the trails are even pet and child friendly, so you can make it an activity for the whole family!

Once you’re done hiking one of the beautiful trails below, you can find some fresh lobster for lunch and enjoy one of the many museums or historic landmarks near Boston. For being a relatively small state, there is a lot to see and do for tourists and residents alike.

1. Mount Norwottuck

Credit: Roger Bilisoly / Flickr

This loop trail is located near Amherst, Massachusetts, and is within Mount Holyoke State Park. This trail leads hikers to the highest peak in the Holyoke Range, which boasts a spectacular view that makes the journey worth the effort.

The trail may take hikers anywhere from 1.5-2 hours to complete. You may find yourself stopping frequently to enjoy nature and the many species of birds that call this area home. Bring your binoculars for some prime bird spotting!

There are a few sections that require minor scrambles, but nothing technical. This is a great hike for beginners who are ready to take on a more challenging trail. A pro tip before your hike is to download a map of the trail, as the physical markings may get unclear at times.

Difficulty: Moderate
Distance: 3.4 Miles
Total Elevation Gain: 626 Feet

2. Blue Hills Skyline Trail

Credit: Bob P. B. / Flickr

This trail is located within the Blue Hills Reservation, which is around 10 miles south of the city of Boston. The reservation has over 120 miles of trails. There are many great views, especially during the fall as the leaves begin to change color.

The best time to hike this particular trail is between March and November. The weather is still comfortable and the path isn’t yet covered in snow and ice, which can make it a bit more treacherous.

Hikers will go through swamps, ponds, marshes, and even meadows along this hike. There are various photo opportunities and if you keep your eyes peeled, you may spot one of the several endangered animal species that call this reservation home.

Difficulty: Hard
Distance: 15.2 Miles
Total Elevation Gain: 3,523 Feet

3. Boston’s Freedom Trail

Credit: Greg Valiquette / Flickr

This is one of Boston’s most popular trails. If you’re looking to discover the rich history of this city, the path leads you through a series of historic sites that date back to the American Revolution. This is a great family hike, as it’s educational and easy enough for children and older adults.

Hikers will begin at the Boston Common and meander towards Charlestown and the USS Constitution. In total, there are 16 sites — which can easily take an entire day.

The path is wheelchair accessible. In certain sections, wheelchair users may need assistance in managing the steeper sections. There are also benches along the path for breaks.

Difficulty: Easy
Distance: 3.4 Miles
Total Elevation Gain: 170 Feet

4. The Cascades Trail

Credit: Shutterstock

This out-and-back trail is near North Adams, Massachusetts. It’s popular with birders, hikers, and trail runners. While dogs are welcome, they must be leashed the entire time.

The trailhead can be a bit difficult to spot. Reviews recommend parking by the YMCA and elementary school and following the signs towards the trail.

There is a great deal of tree coverage, so there is plenty of shade during the hot days. The payoff at the end of this hike comes in the form of a beautiful waterfall and a swimming hole. Be warned, the rocks near the water can be slippery so caution is advised.

Difficulty: Easy
Distance: 2.2 Miles
Total Elevation Gain: 275 Feet

Related Read: 34 Best Romantic Getaways In Massachusetts

5. Skyline Outer Reservoir Loop

Credit: Qianqian Fang / Flickr

This loop trail is in Middlesex Fells Reservation, which is a popular hiking spot near Medford, Massachusetts. Hikers and trail runners generally enjoy this trail from March to November. Dogs are allowed on a leash.

Several paths overlap with this one, so keep your eyes on the trail signs if you don’t want to get off the designated trail. Multiple segments of the path get rocky, so proper footwear with good tread is advised.

You’ll go by several ponds, making for a serene afternoon hike in nature. Though you’re close to Boston, you’d never guess it once you’re in the wooded section of the trail. If you plan to hike the entire length, make sure to pack plenty of water and snacks.

Difficulty: Moderate
Distance: 8.0 Miles
Total Elevation Gain: 990 Feet

6. Mount Greylock via Bellows Pipe Trail

Credit: Steph Uhde / Flickr

This out-and-back trail is in Mount Greylock State Reservation which is near Adams, Massachusetts. Hiking the entire trail may take anywhere from 4-5 hours, depending on the weather and your ability and experience.

It’s recommended to visit this path from April to November, for the most ideal conditions. If you’re bringing your pup along, there are off-leash areas for them to run around and play in nature. There is a decent amount of uphill terrain, so ensure frequent breaks.

The beautiful view at the end of the trail is well worth the strenuous hike. There is a small waterfall, which adds to the beauty of the summit. Naturally, you may find a crowd of people at the top of this hike as visitors can also drive to the overlook.

Difficulty: Hard
Distance: 6.5 Miles
Total Elevation Gain: 2,260 Feet

7. Ponkapoag Pond Trail

Credit: Kael / Flickr

Another popular route within the Blue Hills Reservation is this pond loop. It generally takes 2-3 hours to explore in its entirety. Dogs are welcome but there are no off-leash areas. This is a great route for beginners to tackle, despite the length.

The trail is mostly flat, so you won’t be traversing many rocky hills. During the winter, the pond freezes over and you may see ice skaters and ice fishermen enjoying the frozen water.

The path itself is surrounded by trees and gently rolling hills. There are small inclines along the wide trail. They’re easy to navigate and don’t add a great deal of effort to the overall hike.

Difficulty: Easy
Distance: 6.7 Miles
Total Elevation Gain: 288 Feet

8. Walden Pond Path

Credit: Shutterstock

Walden Pond State Reservation is situated near Concord, Massachusetts. The 335 acres of property are protected due to this being the home that inspired the late Henry David Thoreau. There is a daily fee of $8 for Massachusetts residents and $30 for out-of-state visitors.

This trail is great for families and young children should have no problem meandering along the path and enjoying the beautiful scenery. There is a visitor center that has public restrooms available. No dogs are allowed on the reservation.

Difficulty: Easy
Distance: 1.9 Miles
Total Elevation Gain: 72 Feet

Related Read: 20 Best Hiking Trails in Connecticut

9. World’s End Trail

Credit: Shutterstock

This trail has beautiful views of the Boston skyline that make for great photo opportunities. Hikers can visit Boston Harbor Islands National Recreational Area near Hingham, Massachusetts for birding and hiking opportunities.

The trail is well-maintained and features hilly segments, as well as a rocky peninsula. During the springtime, the meadows are blossoming with wildflowers. There is a $15 fee that is charged per vehicle.

If you come in the morning or near dusk, you’re likely to spot wildlife such as deer and the variety of birds that call this recreational area home. Visitors come back time and time again and the views never fail to impress.

Difficulty: Easy
Distance: 3.8 Miles
Total Elevation Gain: 282 Feet

10. Lynn Woods Reservation

Credit: boredteenager / Flickr

This loop trail is unsurprisingly located in Lynn, Massachusetts. Prepare for a 1.5-2 hour hike if you plan to cover the entire 5 miles of trail. You may pass by horseback riders and mountain bikers, as this is a multi-use path.

For ideal conditions, plan your hike between May and October. Though it has a moderate rating, this trail is great for young children who have some previous trail experience. There are serene views of the many ponds, as well as sections with minor rock scrambles.

Dogs are welcome but they must remain leashed and close to their owners. The trails are wide, allowing everyone to have their own space.

Difficulty: Moderate
Distance: 5.0 Miles
Total Elevation Gain: 328 Feet

11. Bash Bish Falls Trail

Credit: James Robertson / Flickr

Bash Bish Falls State Park has several trails to offer, this one being a moderate and short out-and-back trail. Don’t let the two-mile distance fool you, you’ll get a decent workout in once you hit the wooden steps.

There is a cascading waterfall that washes into a natural pool. No swimming is allowed, unfortunately. The rocks near the waterfall can get slippery, so wear appropriate footwear and proceed with caution.

This is a popular area for camping and fishing, so you’re likely to run across other outdoor enthusiasts. The trail can get a bit busy on the weekends, so head out early if you want a quieter hike.

Difficulty: Moderate
Distance: 2.1 Miles
Total Elevation Gain: 521 Feet

12. Southern Middlesex Fells Loop

Credit: Qianqian Fang / Flickr

This trail is popular with hikers, mountain bikers, and snowshoers during the wintertime. There are many elevations and descents, making for a moderately challenging hike that pays off in views of pine forests and sweeping meadows.

If the parking lot is already full once you arrive, you can park on one of the side streets and walk to the trailhead.

It’s recommended that hikers download a map onto their mobile devices, as the trail markings aren’t always easy to follow.

Some areas require minor rock scrambling. The rest of the trail is mostly wooded and it can feel very secluded and quiet.

Difficulty: Moderate
Distance: 3.0 Miles
Total Elevation Gain: 360 Feet

13. Battle Road Trail

Credit: Stephen St-Denis / Flickr

This point-to-point trail is near Concord, Massachusetts, and is lined with historical buildings. There are many benches and picnic areas for breaks. With so much rich history, this trail is a great option all year long.

There is a visitor center onsite, which has restrooms for public use. The trail is mostly flat and made up of packed sand and gravel. Wheelchair users should be able to manage the pathway with a bit of help.

Hikers of all ages will enjoy the educational offerings of the trail, as well as the wildlife and flowers that are active during the spring.

Difficulty: Easy
Distance: 4.6 Miles
Total Elevation Gain: 239 Feet

14. Great Blue Hills via Coon Hollow Path

Credit: David Garcia / AllTrails

This out-and-back trail can be hiked in under an hour, making it a great option for a morning or afternoon workout. The best times to visit are between April and October. You’re likely to run into other hikers, as well as some bird enthusiasts.

Hikers will enjoy the broad trails that lead to an observation tower. The views from the top are expansive. Due to the relatively flat terrain, this is a great hike for families with kiddos. There is a brief segment with rocky terrain but it’s not difficult to traverse.

During the winter, the path can get slippery due to the ice. If you hike during this time, you should bring poles and boots with good traction.

Difficulty: Easy
Distance: 1.5 Miles
Total Elevation Gain: 367 Feet

15. Mount Tom via New England Trail

Credit: Shahid Durrani / Flickr

This out-and-back trail is near Holyoke, Massachusetts. Hikers should plan for a 2+ hour hike if they plan to do the entire path. Dogs are welcome but must stay leashed and close to their owner.

There is a charge to enter Mount Tom State Reservation and it’s charged per vehicle. There is a higher fee for non-residents but there is a park-specific pass available that is good for a year.

The pathway is well-marked and there is more than enough parking. There is a relatively steep ascent near the beginning of the hike but then it levels out. It can become slippery after heavy rainfall.

Difficulty: Moderate
Distance: 3.9 Miles
Total Elevation Gain: 990 Feet

Related Read: Best Time to Visit New England

16. Arnold Arboretum Trail

Credit: Robert Cross / Flickr

Located near Jamaica Plain, Massachusetts, this loop trail is best visited between March and October. Dogs must be leashed but are welcome to come along for the fun.

This trail is a quick escape from the hustle of urban life and with so many tree species to study, you may pick up a new arborist hobby. Parking can be difficult at times but vehicles are allowed to park along the street leading up to the trailhead.

The trail is a mix of paved and gravel paths, featuring gentle inclines. You can add or subtract from the mileage by hopping onto one of the other paths that branch off of this one.

Difficulty: Easy
Distance: 3.7 Miles
Total Elevation Gain: 314 Feet

17. Cliff Pond Trail

Credit: Massachusetts Office of Travel & Tourism / Flickr

Cliff Pond Trail is located in Nickerson State Park, which is near Brewster, Massachusetts. Avid hikers can easily complete this trail in under an hour for a quick outdoor adventure.

The area is a popular spot for birders and fishers. For those wanting to bring their canine friends along, there are areas for them to be off-leash. Overall, this is a quiet hike if you’re looking for solitude.

The trails are well-maintained and the beaches are pristine. Be careful of poison ivy and don’t trip across any exposed roots.

Difficulty: Easy
Distance: 2.7 Miles
Total Elevation Gain: 78 Feet

18. Pearce Lake and Upper Pond Trail

Credit: Kristian Travis / Flickr

As its name implies, hikers will come across water on this hike and there are even spots that are prime for fishing. The trail is located within Breakheart Reservation which is located in Saugus, Massachusetts.

The ideal time to visit is between May and October. If you plan to bring your pup, there are off-leash designated areas for them to get a taste of freedom.

You can bring picnic lunches to the area but there are no trashcans. You must pack out your garbage. The trail can get crowded around the afternoon, so get an early start if you’re looking for peace.

Difficulty: Moderate
Distance: 2.4 Miles
Total Elevation Gain: 154 Feet

Related Read: 20 Top Treehouse Rentals in Massachusetts

19. Bare Mountain

Credit: Dana F / Flickr

If you’re looking for an efficient morning hike that leaves you slightly out of breath, this is a great option. You can hike Bare Mountain in under an hour and the slight elevation will keep your heart rate up.

There are several side trails that you can add to your mileage. This is a great hike for kids, as it’s short but allows them to challenge themselves on mild scrambling and steep portions.

Dogs are allowed to join their families on the adventure but they must be leashed. The best time to visit is between April and November but always check the weather before you head out.

Difficulty: Moderate
Distance: 1.1 Miles
Total Elevation Gain: 488 Feet

20. Mount Toby Trail

Credit: Najwa Aswad / Flickr

Mount Toby State Forest is located in Sunderland, Massachusetts, and is a great spot for hikers to escape into the serenity of nature. This particular trail features a waterfall and a decent workout from the elevation.

The path is kept in good shape and there is plenty of tree cover. Reviews mention that going clockwise will allow you to traverse the steep rocky section going downhill instead of up. If you want the best view, climbing the fire tower allows you to see the area from a bird’s eye view.

Dogs are welcome but there are no off-leash areas for them to run and play. The rocky sections may be rough on their paws, so bring the appropriate gear.

Difficulty: Moderate
Distance: 4.4 Miles
Total Elevation Gain: 935 Feet

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