By Madeline Bilis
August 20, 2019
Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.
Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

The gentle hills of Greater Boston aren’t exactly known for their heart-pumping hiking trails. The same goes for the sloping dunes of Cape Cod — you’d be hard-pressed to find gaggles of L.L. Bean-clad hikers trekking out to sandbars in Eastern Massachusetts the way some groups scale the mountains of Western Mass. And that’s exactly why it’s so wondrous to go hiking there.

I know this because I spent the better part of last year hiking around Eastern Massachusetts to write an aptly named guidebook, "50 Hikes in Eastern Massachusetts." It details some of the most well-known trails beyond Boston, as well as the area’s more secret, under-the-radar walks.

Indeed, one of the region’s biggest strengths as a hiking destination is a refreshing lack of other humans. Maybe uncrowded trails are a given, but until you go for a leisurely stroll among centuries-old trees — without seeing another person for hours — you might not understand the magic. (During my almost seven-mile jaunt along Wellfleet’s Great Island Trail, one of the only other living beings I saw besides my hiking partner was a harbor seal splashing in the bay.)

Related: The Perfect Three-Day Weekend in Boston

The other thing that makes this overlooked spot shine is its varied landscapes. There’s the option to climb a 635-foot hill to see views of the Boston skyline in the Blue Hills, or just 14 miles down the road, find flat walking trails that meander through abandoned military bunkers at Wompatuck State Park. Pleasant pond walks, island adventures, and foliage-filled journeys are all within an hour’s drive of each other.

Ahead, find 10 of my favorite trails. You can check out all 50 hikes in my book, available here.

Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

1. Noanet Woodlands

Where: Dover, Mass.
Total distance: 2.75 miles
Hiking time: 1 hour 30 minutes

Bostonians in search of leafy solace might consider the Noanet Woodlands in Dover a hidden gem — after all, the Trustees-owned property is only 16 miles outside the city. Locals know better, though, and tend to get there early before the 30-car parking lot fills up.

The reward of this reasonably easy climb is Noanet Peak, a rocky ledge with lovely views. On a clear day, you can spot the buildings of the Boston Skyline to the north — it’s especially beautiful during peak foliage season. The descent is followed by a leisurely stroll past a scenic pond and former mill site.

Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

2. The Great Island Trail

Where: Wellfleet, Mass.
Total distance: 6.8 miles
Hiking time: 4 hours

The Great Island Trail is arguably one of the best hikes in all of Massachusetts. The loop, located within the boundaries of the Cape Cod National Seashore, begins with an easy walk tracing the shoreline of “the gut,” where the Herring River lets out into Wellfleet Harbor. Then, it climbs up into a pitch pine forest, offering stunning views from cliffs overlooking Cape Cod Bay.

There’s also a history lesson thrown in, as a small stone monument marks the spot where a former 17th-century whaling tavern once stood. The trail emerges from the woods and traverses sandy dunes leading to Great Beach Hill, and ends with a breezy walk along the beach. While Great Island is no longer a true island, it sure feels that way with its abundance of ocean panoramas.

Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

3. Mount Watatic

Where: Ashburnham, Mass.
Total distance: 3 miles
Hiking time: 2.5 hours

Mount Watatic is a monadnock, defined as rocky hill or small mountain rising from a mostly level surrounding landscape. (For those thinking of Mount Monadnock in New Hampshire, a “monadnock” is a type of land formation, as well as the name of the Jaffrey, N.H., peak that lines less than 20 miles north of Watatic.) The 1,832-foot mountain is one of the highest east of Massachusetts’ Connecticut River, and is often visited by bird-watchers, as it is one of the most popular spots for hawk observation in the Northeast.

A journey to the top culminates with views all the way to the Green Mountains in Vermont, and to the peaks of southern New Hampshire. If weather permits, Boston can be seen in the east, while suburban towns dot the land before it. Hikers will spot farms, mountains, hills, a fire tower, and more.

Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

4. Halibut Point State Park

Where: Rockport, Mass.
Total distance: 1.5 miles
Hiking time: 1.5 hours

The granite cliffs that Halibut Point is known for are a whopping 440 million years old. The sheets of rock, which drop off along the coastline, proved to be invaluable to the peninsula’s range of residents over the years, from the Pawtucket tribe to early settlers. The area is best remembered, however, for its booming granite quarry. After a few minutes on the trails, hikers will spot the gaping hole left from the former seaside quarry. It’s been filling with rainwater since the quarry was abandoned in 1929, after Cape Ann’s granite industry faltered. Now, with its almost turquoise tint, the water makes a stunning backdrop for a few trail photos.

The state park’s trails circle the quarry, and traces of its not-so-distant past can be spotted along the way. From dog holes, or rows of depressions that allowed workers to split the granite, to large iron staples that held cables, it’s worth trying to spot all of the man-made additions to the landscape. Don’t miss the detour to the park’s towering grout pile, made up of discarded granite pieces. From the top, visitors can enjoy a panoramic view of the Atlantic.

Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

5. Blue Hills Reservation — Skyline Loop

Where: Milton, Mass.
Total distance: 3 miles
Hiking time: 2.5 to 3 hours

Its boulders aren’t made from sapphire, and its trees don’t grow cerulean branches, but the Blue Hills are undeniably blue. The reservation’s name comes from the observations of early European explorers who glimpsed the peaks from their boats along the Massachusetts coastline. On the exposed hilltops, a type of granite called riebeckite appeared blue from their watery distance.

As one of the Blue Hills Reservation’s most popular trails, the Skyline Loop is also one of its most dangerous. This 3.5-mile trek is somewhat challenging, and requires some climbing to reach the top of Great Blue Hill, which is the highest peak on the East Coast from Boston to Miami. At the top, a rectangular construction called Eliot Tower offers sweeping views from the Boston skyline and harbor all the way to nearby Quincy. On a clear day, hikers can see Mount Wachusett and the Worcester Hills to the west, and the Monadnock region of New Hampshire to the northwest.

Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

6. Breakheart Reservation

Where: Saugus and Wakefield, Mass.
Total distance: 4.25 miles
Hiking time: 4 hours

Legend says Breakheart Reservation got its name during the Civil War, when troops training there felt the place was remote and lonely, and in turn, broke their hearts. One historian argues the land was named after Breakheart Hill in Gloucestershire, England, the original home of an early Saugus settler. Whatever its origins are, one thing is clear: Breakheart is rich in wildlife and history.

This hike connects several short trails and crosses a total of five hills. The reservation’s 700 acres of pine-oak forest offer lovely views of Boston from rocky hills and ledges, while freshwater ponds act as refreshing spots to cool off in the summertime.

Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

7. Walden Pond

Where: Concord, Mass.
Total distance: 2.25 miles
Hiking time: 1 hour 30 minutes

History lovers, meet your match. Walden Pond State Reservation is the spot where in the 1840s, Henry David Thoreau famously spent two years living in a cabin near the shores of the pond. It was an experiment he hoped would bring him closer to nature. The first draft of his most famous work, "Walden," was written during his time there, and sings the praises of using nature to forge meaningful connections among the physical and spiritual worlds.

This hike skirts the edges of Walden Pond, taking a few detours deeper into the woods along the way. One such detour is to the site of Thoreau’s cabin. The site, in all its glory, is marked by a granite bollards connected with chains. In the center, a stone marks the cabin’s chimney foundation, and a sign proclaims one of "Walden’s" most quotable snippets. Beside where the cabin once stood, there’s a monumental display of stone cairns created by visitors from all over the world. Consider flipping through a copy of "Walden" before setting out on this journey.

Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

8. Borderland State Park

Where: Easton and Sharon, Mass.
Total distance: 6.3 miles
Hiking time: 3 hours 25 minutes

Plenty of visitors to Borderland State Park arrive with the intention to play a few holes of disc golf. Others come to admire the art and architecture of the former estate’s 1910 stone mansion. But the park’s hiking trails are its true highlight, spanning 1,772 acres.

Put simply, Borderland is one of a kind. It lies at a border in several senses of the word — it sits literally on the border of the towns of Sharon and Easton, it once divided the territory of Native American tribes, and is home to a border between gentle hills in its northern section and flatter land to the south. The park was once the estate of Harvard botanist Oakes Ames and his wife Blanche. Oakes was one of the country’s earliest researchers of orchids, while Blanche was an artist, author, and inventor. Blanche teamed up with Oakes to produce scientifically accurate orchid illustrations for his research, and together they created a body of work that led orchids to become the most-documented plant species — ever.

Today, Borderland is home to a range of plant and animal life. Water lilies thrive in the park’s six ponds, while deer, rabbits, otters, and other critters make their homes on land. Embark on this more than 6-mile journey to see them all, plus a film location for the movie "Shutter Island."

Related: The Best Inns in New England

Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

9. Peddocks Island

Where: Hull, Mass.
Total distance: 4 miles
Hiking time: 2 hours

Peddocks Island is one of the largest islands in Boston Harbor. It’s only accessible via an interisland ferry from the city, which makes it feel more remote than some of the other nearby islands.

A hike through the curving hunk of land starts with a walk through forests, then along the coastline, and around the paved paths of a former military fort. Along the way, hikers will notice diverse wildlife — and learn a bit of history. Many people have called the island home over the years, from Portuguese fishermen to prisoners of war. The island harbors plenty of secrets, too, like long-ago drunken parties in a notorious inn, and when bootleggers stashed bottles in Peddocks’ coves. A walk around the island only skims the surface of the place’s rich history.

Photo by Madeline Bilis / Reproduced by permission of The Countryman Press. All rights reserved

10. Wompatuck State Park

Where: Hingham, Mass.
Total distance: 4.8 miles
Hiking time: 2.5 hours

Wompatuck State Park, lovingly called “Wompy” by locals, stretches to almost 3,600 acres, covering a large swath of Hingham, as well as parts of Cohasset, Norwell, and Scituate. The land was originally owned by a Native American chief known as Josiah Wompatuck, and much later, became a naval ammunition depot. Cement bunkers were built there to store munitions, but the depot was deactivated in the 1960s. The bunkers, however, are still visible to state park visitors. One such bunker, called N-9, was renovated by three Eagle scouts in 2008. It’s now covered in colorful graffiti. Set out on this five-mile hike to wind through bunkers, woods, and meadows.

Advertisement