15 Best Hikes In Massachusetts To Experience

Nestled on the east coast, Massachusetts is a quintessential New England state that’s so beautiful and totally historic to explore. From the gorgeous places in Boston to little gems like Martha’s Vineyard and Cape Cod, it’s one of the most epic places in the USA to visit. This is especially true if you love the outdoors, with some of the best hikes in Massachusetts dotted all across the state.

We had the best time exploring Massachusetts! Between our love of Boston, gorging on all the fresh lobster (that is so delicious in Massachusetts) and exploring the state by foot, it’s quickly become one of our favourite spots to revisit. I mean, anywhere with lobster and views is a win for us!

You see, Massachusetts is pretty diverse (for a relatively small state) and you can easily explore lots of the state via the established trails that crisscross the regions. So, to make things a little easier, I’ve popped a few of the best hikes in Massachusetts that we totally love.

Some of our hikes are a total stroll, whilst others will make you sweat and earn your pudding! So, be sure to choose the right hike that fits your experience and fitness levels. Oh, and always hike with care!

Take a look, below, at the best hikes in Massachusetts. Have the most epic trip!

1.) Ipswich River Wildlife Sanctuary, Topsfield

Located in Topsfield (around 40-minutes drive from Boston), there are over twelve miles of trails spread out over this sanctuary to explore.

Most, if not all are relatively easy hikes and some are considered more of a long walk that is suitable for the whole family! For instance, the Rockery Trail will take around 45-minutes to walk and is almost totally flat and easy to enjoy. If you fancy a longer stroll, head on the South Esker Loop trail that’s just over 2-miles in length.

This is an absolutely incredible opportunity if you love spotting wildlife, too. Here, you will catch a glimpse of river otters, turtles, wetland birds and even the occasional deer! In the summertime, this is an excellent place to canoe or kayak as well and really easy to visit from Boston for an afternoon galavant from the city.

2.) Mount Norwottuck, Mount Holyoke State Park

Located in Mount Holyoke State Park, this is a fairly strenuous hike that is just over three miles long. It’s one of the best hikes in Massachusetts if you fancy something that’ll work up a sweat, but won’t have you crawling back down the mountain!

You will ascend to the summit of Mount Norwottuck, which stands over 1,100 feet tall, and from the summit, you’ll get a glimpse of the breathtaking view of the Connecticut River Valley; just stunning!

That being said, the real highlight of the walk comes on the return trip, where you can visit the Horse Caves. These caves, which are in reality closer to overhangs, are rich in history, having been used by the rebels during Shay’s Rebellion.

3.) The Skyline Trail Loop, Middlesex Fells Reservation

Incorporating over 6,000 acres of land that is managed by the Department of Conservation and Recreation that’s a total beaut to visit.

The skyline trail is the most famous hike in this state park, known for its spectacular view of the Boston skyline at the summit.

This is a uniquely beautiful spot to rest and refuel before beginning the descent. The moderate trail is approximately nine miles long and takes anywhere from four to six hours to complete.

Now, just remember that these trails can get super busy on the weekends. If you need parking, arrive early as spots fill up fast.

4.) The Freedom Trail, Boston

You can’t mention the best hikes in Massachusetts and not mention the Freedom Trail.

Taking in all the historical sites of Boston, the Freedom Trail is a world-famous, easy-to-walk (2.5 mile) route that meanders Boston’s historic downtown. Along the way, you’ll get to see some of the most significant places in the history of colonial America and the development of Boston itself.

Stand on the star that marks the spot of the Boston Massacre, visit the Paul Revere House and Faneuil Hall, walk the decks of the famous battleship “Old Ironsides” before ending the hike by climbing the stairs to the top of Bunker Hill.

It’s up to you how you walk this route; you can either participate in a guided walk or simply follow the yellow bricks that mark the path for a self-guided tour.

5.) Purgatory Chasm Trails, Purgatory Chasm State Reservation

This is an awesomely unique hiking experience for all ages, with so many different trails to choose from.

For an easy stroll, hop on the Purgatory Chasm Loop and Purgatory Brook Trail. With over two miles of fairly easy to walk pathways, you’ll get to wander through the region that’s pretty easy to navigate with the free downloadable parks map (see here).

Have the best time!

6.) Bish Bash Falls Trail, Bish Bash Falls State Park

Here, you’ll experience the highest single-drop waterfall in Massachusetts either by hiking from the top down or in the reverse direction.

In either instance, the hike is centred around the iconic Bish Bash Falls, which most New Englanders (in the state) know about. This is a wonderful option for anyone who is looking for a quick yet scenic walk, as the 2-mile long trail takes less than an hour to complete.

Although an easy trail, be extra careful in the chillier months as the trail can get icy and slippy!

7.) Harrington Trail, Mount Wachusett

This is perhaps the most popular (moderate) hikes on Mount Wachusett, which is the highest point in the state east of the Connecticut River.

Around 3-mile hike is fairly easy for experienced hikers, though you might find it a challenge if you haven’t hiked before.

Leading you through a lush green forest before achieving the ultimate view at the mountain’s summit, you’ll quickly realise why this is one of the best hikes in Massachusetts to enjoy the great outdoors.

Now, the hike itself is located in the town of Princeton, which is a wonderful place to stop for a well-deserved meal and tipple afterwards. Pop into the Mountain Barn, which has local craft beers coupled with a tasty dishes that’ll fill you up in no time. Their sesame ginger tuna and peanut butter pie are both so good!

8.) Mount Greylock, Mount Greylock State Reservation

There are many different trails around Mount Greylock that’ll get you right to the summit. Though, being the highest point in the entire state of Massachusetts, it’s not always going to be the easiest of hikes.

For a harder trail, for the experienced hikers amongst us, head on the Bellows Pipe and Thunderbolt Trail. It is tough and really is for those that are experienced hikers.

For something a little easier, head on the Chesire Harbour Trail. Yes, it’s a tad longer but the inclines aren’t quite as tough. Still, though, this isn’t for a “new to hiking” kinda person.

At the top, you are treated to a panoramic view of five states, a sight which is particularly delightful in the fall foliage.

9.) Robert Frost Trail, Massachusetts

A colossal trail spanning around 47-miles, the Robert Frost Trail (downloadable free guide, here) is one of the best hikes in Massachusetts that you can hop on or off wherever you are. This all means you don’t have to complete the whole trail in one large swoop!

This is a gorgeous walk through the New England woods, yet towards the end of your journey, you encounter a fire tower at the top of Mount Toby that provides majestic views that are certainly worthy of the greatest poet!

If you do end up going in the chillier months, you must pop on some suitable winter hiking shoes (and potentially crampons) that’ll deal with the ice.

10.) Mount Holyoke, Mount Holyoke Range State Park

This seven-mile-long trail leads alongside the ridgeline of Mount Holyoke, which rises approximately 935 feet tall and is totally gorgeous.

Aside from the spectacular views at the top, this hike is a wonderful opportunity to view the fossilized footprints of dinosaurs, too! These treasures can be found all over the greater Holyoke area. Keep your eyes peeled!

Now, there are actually many trails to join around Mount Holyoke, so, depending on your experience, choose one that’s right for you. Take a look at the Parks’ trail map, here.

11.) Salem Heritage Trail, Salem

Probably one of the more famous spots in the state, Salem is well known for its infamous Witch Trials! This was a pretty gruesome part of colonial history in which many accused witches were executed.

Today, you can walk the legendary witch trail either as a guided group or by yourself following the Salem Heritage Trail.

Along the way, you’ll take a gander around the Salem Witch Museum, the Broad Street Cemetery, the Witch House as well as Gallows Hill. It’s relatively easy and a great stroll whilst exploring Salem.

Oh, and if hunger strikes pop into Turner’s Seafood or the Sea Level Oyster Bar.

Both are great calls for some of that tasty Massachusetts seafood.

12.) Racebrook Falls and Mount Everett trail, Mount Everett

This is a very challenging hike, to say the least. At around 6-miles in length, it’s a trail that should never be experienced by anyone other than pro hikers that know exactly what they’re doing.

Taking in Race Brook Falls, a group of waterfalls that is absolutely staggering in their beauty, you’ll find lots of places to stop and chill but it is tough, be warned!

You’ll also get some stunning views of the world-famous Berkshire Mountain Range from the summit, too. Gorgeous.

13.) Cape Cod Rail Trail, Cape Cod

The Cape Cod Rail Trail is a 22-mile stretch of pathway that connects through a number of Cape Cod’s stunning towns to visit.

Suited either to walkers or bikers, it’s one of the best hikes in Massachusetts that doesn’t even feel like a hike and more of a stroll. Relatively flat and easy, you can start and stop wherever you please.

You can download the full trail map (for free), here.

14.) Martha’s Vineyard Trails, Martha’s Vineyard

There are lots of hikes and rambling routes on Martha’s Vineyard, with most taking you all across the island.

For a 3-hour, join the Menemsha Hills Reservation that’ll get you up pretty high (as heights on the island go). From here, you’ll get to see all across the region and spot the Elizabeth Islands, too!

You’ll also find some gorgeous and unspoilt trails around Menemsha Hill and Great Rock Bight Preserve. Honestly, they’re lovely areas and it’s almost impossible to get totally lost here.

Finally, download the Trails MV App that showcases a whopping 200-miles of trails and spots to see on Martha’s Vineyard.

15.) Appalachian Trail, across states

Spanning thousands of miles long, the Appalachian Trail goes straight through western Massachusetts and is pretty easy to join if you want to complete a New England section.

Going through Mount Greylock State Park, Clarksburg Forest, Goose Pond and Mount Wilcox, you’ll get to see so much of the western fringes of the state. It’s easily one of the best hikes in Massachusetts if you’re up for a big one!