15 Best Hikes in Massachusetts: Waterfalls, Mountains & More!


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Massachusetts is known for many things, and while great hiking might not be one of the first things that comes to mind when thinking of the Bay State, there are plenty of MA hiking adventures to be had. That’s why today we’re taking a look at some of the best hikes in Massachusetts!

With over 450,000 acres taken care of by the Bureau of State Parks and Recreation and over 2,000 miles of trails, you’re sure to find plenty of memorable Massachusetts hiking trails!

The Bay State has some beautiful places to explore, so let’s get right to it and check out some of the best hikes in MA!

MA Waterfall Hikes

Did you know there are over 400 waterfalls in Massachusetts? Needless to say, it’s not hard to find Massachusetts hikes with waterfalls! Here are some of MA hikers’ favorites.

Bash Bish Falls

Perhaps the most well-known and loved falls in the state, Bash Bish is located in its namesake state park near Mount Washington, MA. Plummeting 59ft down a steep rock face into a boulder-strewn creek below, it is Massachusetts’ tallest waterfall.

You can get to the falls one of two ways: Starting at the Upper Falls and making a steep descent down alongside Bash Bish or taking one of the trails in from the bottom. The latter is a 2-mile out-and-back and travels along the rocky banks of the brook through a shady forest before getting up-close views of this magnificent double waterfall.

Large waterfall and small waterfall cascade down rocks on a Massachusetts hike.
Massachusetts’ waterfall hikes should definitely be on your MA bucket list.

Doane’s Falls

Another popular waterfall in Massachusetts to hike to is Doane’s Falls. Located near Royalston, this area offers not one, but three cascades to explore. Doane’s Falls itself plunges an impressive 175ft altogether over a series of drops.

There are a couple of different routes to get to the falls. If you’re short on time or have young kids with you, you can opt for the short half-mile hike from Tully Lake Park. If you’re ready to embark on an all-day adventure, there is a 7.5-mile loop trail as well.

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Wahconah Falls

Located within its own state park as well, Wahconah Falls is another popular destination for Massachusetts’ nature-lovers. This 40ft tiered waterfall begins with a series of smaller cascades before converging and meandering down a series of rock terraces before plunging into a deep pool at the bottom.

The easy half-mile trail leading to the falls wanders through a lovely mix of hardwood and evergreen trees. Be sure to go early as this area can become crowded!

Berkshires Hikes

Although we’ve already covered some hikes in the Berkshires above as many of the state’s waterfalls are located in this region, there are plenty of other great hiking opportunities in this beautiful area of Massachusetts! Here are a couple of the most scenic hikes in the region, plus our entire list of top Berkshires hikes.

Stevens Glen

This lush, tranquil area will have you feeling as if you just stepped into a fairytale! The Stevens Glen Trail is a modest 1.5-mile loop and is mostly easy, though it does have some steep sections along the way.

The creek is noted to be a great place to soak your feet on a hot day and, if you’re not sick of waterfalls yet, you’re in luck as there is a narrow waterfall that passes through a tight ravine. Be sure to take a well-deserved break at the observation deck there as well!

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Hoosac Range Trail

Located near North Adams, this trail is definitely for those seeking more of a challenge. The Hoosac Range Trail, which heads up to the summit of Spruce Hill (2,543ft), winds its way through the forest and along a ridgeline for about 3-miles one-way. The ascent is fairly gradual, but you will gain about 900ft along the course.

Several viewpoints are available, including the spur trail to must-see Sunset Rock. (If you don’t feel like a 6-mile hike, it is about 1.6-miles just to Sunset Rock.) Don’t forget your camera as you’ll want to get some pictures of those awesome vistas!

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Landscape view of fall foliage under a blue sky on a Massachusetts hiking trail.
Hiking in Massachusetts in the fall is fall foliage heaven!

Eastern MA Hikes

Love the city, but just need some peace and quiet sometimes to recharge? You might be surprised by the number of hikes near Boston! If you’re looking for some nature therapy in the eastern half of the state, here are a couple of our favorite hikes in MA!

Skyline Loop

If you need a breather from the city but don’t want to drive too far out in the sticks, the Skyline Loop is your best bet. This trail is located within the Blue Hills Reservation and is only about 16 miles from Boston, making it just far enough away you can relax, but not so far away it’s inconvenient.

The Skyline Loop is only 3-miles long, but you’ll be climbing up and down several hill summits, including the tallest one in the park: Great Blue Hill. Be sure to check out the observation tower while you’re up there for panoramic views of the Boston skyline.

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Noanet Peak Trail

For a similar hike in the Dover area, check out the Noanet Peak Trail in the Noanet Woodlands. This 3-mile lollipop loop trail takes you up a couple hundred feet to the top and would be considered moderate, at most.

Other than the great view of the distant Boston skyline, you’ll also pass several ponds along the way and there is even an old mill site to check out. For extra beauty, head to the Noanet Trail in the spring to view the wildflowers!

Western MA Hikes

For some truly scenic Massachusetts hiking, you can’t beat the gentle hills, mountains, streams, and more of the western half of the state. Check out these two iconic hikes to experience the beauty this region has to offer!

Feet in hiking boots on a forest hiking trail in Massachusetts.
Lots of lovely hiking trails in Massachusetts to explore!

Chesterfield Gorge

For some of the best hikes in Massachusetts, you can’t beat the trails traversing along Chesterfield Gorge. The Westfield River, which is a National Wild and Scenic River, has carved away at the rock in this area for thousands of years, leaving behind 70-ft high cliffs and mesmerizing cascades. There is a short, easy half-mile trail that runs along the top of the gorge, offering great views from above.

If you’re looking to hike a longer distance, there is a 4-mile out-and-back that runs along the gorge as well. There are plenty of connecting trails in the area, so your hiking possibilities are endless!

Mount Toby Trail

If you’re ready for a moderately challenging hike that rewards you with waterfalls, shady forest, and panoramic views, the Mount Toby Trail is waiting for you! Like most trails on the list, there are several means to get to the top.

One popular option is the lollipop loop trail that covers about 4.3-miles altogether and gains an impressive 920ft. It is very steep, both up and down, so wear your good hiking shoes and take some trekking poles!

Unique Hikes in Massachusetts

Purgatory Chasm

Are you interested in challenging hikes that are unlike your standard walk in the woods or ascent up a mountain? Then you’ll love the trails at Purgatory Chasm State Reservation.

With a natural landscape of giant rock formations, most of the trails at this state park require quite a bit of nimbleness and courage! You’ll find interesting rock formations like the Fat Man’s Misery and the Devil’s Coffin that make for a very memorable hiking experience. Again, this is a pretty challenging Massachusetts hike!

Day Hikes in Massachusetts

Ready for some awesome day hikes in Massachusetts? Whether you’re ready to ascend mountains or take a leisurely stroll along the beach, these two hikes are ones for the book!

Mount Greylock

At 3,491ft tall, Mount Greylock is Massachusetts’ tallest point. With that being said, most trails to the top are rated as moderate and you will gain well above 1,000ft of elevation along the way. Don’t let this put you off, though, because the 90-mile views from the top are worth it! There is also a veterans memorial and lodge at the summit. You might even grab a bite in the lodge’s restaurant!

To get there, try taking the Campground Trail to the Hopper Trail to the summit. You won’t be disappointed with the lush surroundings and shady beech and pine forest on your way there. Mount Greylock State Reservation is a definite must visit, especially in fall!

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Great Island Trail

For a more laid-back hike set in one of Massachusetts’ most popular destinations, look no further than the Great Island Trail located on Cape Cod. The main loop is known as the Tavern Loop and will take you about 4-miles around Griffin Island. You can also take the extension out to Jeremy Point for an 8.8-mile round-trip.

No matter whether you cover the long or short version, this MA trail is great for nature enthusiasts, especially bird-lovers. You should be aware of tides and, while very romantic, walking along sand can become tedious after a while.

Best MA hikes with kids

A pond reflects the trees surrounding it on a bright sunny day on a kid friendly Massachusetts hike
Walden Pond is a gorgeous kid friendly Massachusetts hike!

Walden Pond

Walden Pond State Reservation is 400-acres of protected MA land, and the place where Henry David Thoreau went to “live a deliberate life.” This family friendly MA hike is very accessible for little legs, so this is a great choice for hiking with toddlers.

The pond offers lovely views and you’ll even see a replica of Thoreau’s little home. In the summertime, you can wade and swim in the pond!

World’s End

Located in Hingham, World’s End is a lovely place to go for an easy hike with kids near Boston. Encompassing over 250 acres, there is lots to see and enjoy on this very family friendly nature walk, from following old carriage paths, inspecting salt marshes and coastlines, and even enjoying views of the Boston skyline.

No one is likely to break a sweat out at World’s End, but enjoying such a beautiful natural area so close to Boston is an absolute treat!

Atlantic White Cedar Swamp Trail

One of the prettiest hikes on Cape Cod, Atlantic White Cedar Swamp Trail is an excellent hike with kids. Other than some steep stairs that require extra caution at one point, this is a perfect all ages hike.

Meandering into the woodland, through to the boardwalk that snakes over and across the Atlantic White Cedar Swamp, you and your kids will feel like you’ve been transported to another world! Plus, the loop only takes about an hour, so this is a good MA hike for younger kids with less stamina.

As you can see, there are plenty of places to go hiking in Massachusetts. While many trails in MA may not be terribly challenging due to the state’s topography, you can rest assured you can find an enjoyable hike regardless of what kind of scenery you’re into: Waterfalls, mountains, seashore, and beyond!


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