This Overlooked Region Has Some of the Loveliest Hikes in New England

These nine trails in eastern Massachusetts are wildly underrated.

Fact checked by Jillian Dara

The gentle hills of Greater Boston aren't exactly known for their heart-pumping hiking trails, and 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 along the western swath of the state. And that's exactly what makes the hiking arguably better.

I know this because I spent the better part of a year hiking around eastern Massachusetts to write a guidebook, "50 Hikes in Eastern Massachusetts." It details some of the best-known trails beyond Boston, as well as the area's more under-the-radar walks.

Indeed, one of the region's biggest strengths as a hiking destination is the refreshing lack of crowds on the trails. 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: Boston vacation and trip ideas

The other thing that makes this overlooked area 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 to follow flat walking trails to 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 nine of the best hiking trails in eastern Massachusetts.

Great Island Trail

Where: Cape Cod National Seashore in Wellfleet

Total distance: 8.8-mile return

Difficulty: Challenging

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 the trail passes the former site of a 17th-century whaling tavern. The trail emerges from the woods and traverses dunes leading to Great Beach Hill, ending with a breezy walk along the water. While Great Island is technically a peninsula, its abundance of ocean panoramas give it a real island feel.

Related: Cape Cod Travel Guide

Halibut Point Trail

Where: Halibut Point State Park in Rockport

Total distance: 1.6-mile loop

Difficulty: Easy

The granite cliffs Halibut Point State Park is known for are more than 400 million years old. However, the sheets of rock, which drop off along the coastline, were disturbed to supply Cape Ann's old granite industry. After a few minutes on the trails here, hikers will spot the gaping hole left from the former seaside quarry, filled with rainwater since being abandoned in 1929. Now, with its almost-turquoise tint, the water makes a stunning backdrop for trail photos.

The park's trails circle the quarry, and traces of its not-so-distant past can be observed along the way. Try to spot all the changes to the landscape, from dogholes, or rows of depressions that allowed workers to split the granite, to large iron staples that held cables. Don't miss the detour to the park's towering grout pile, made up of discarded granite pieces. From the viewpoint, visitors can enjoy a panoramic view of the Atlantic.

Skyline Loop Trail

Where: Blue Hills Reservation in Milton

Total distance: Three-mile loop

Difficulty: Challenging

Its boulders aren't made from sapphire, and its trees don't grow cerulean branches, but the Blue Hills are undeniably blue. A type of mineral here called riebeckite gives them their distinctive color. As one of the Blue Hills Reservation's most popular trails, the Skyline Loop is also one of its most dangerous. Reaching the top of 635-foot Great Blue Hill requires some climbing. When you arrive, you'll find Eliot Tower, which is closed for restoration. Check for progress updates and try to plan your hike for after it reopens to get sweeping views of the Boston skyline and harbor from the top.

Breakheart Reservation Outer Loop Trail

Where: Breakheart Reservation in Saugus and Wakefield

Total distance: Two-mile loop

Difficulty: Easy

Legend has it that Breakheart Reservation got its name during the Civil War, when troops training there found the place remote, lonely, and heartbreaking. Another story is that the land was named after Breakheart Hill in Gloucestershire, England, the original home of an early Saugus settler. Whatever its origins are, Breakheart remains a premium hiking destination teeming with wildlife and rich in history.

The Outer Loop Trail circumnavigates the center of Breakheart, featuring views of beautiful pine-oak forest and Boston, about 12 miles down the road. The two-mile path is paved and accessible. It even passes by freshwater ponds that serve as refreshing spots to cool off in the summer.

Walden Pond Loop Trail

Where: Walden Pond State Reservation in Concord

Total distance: About a two-mile loop

Difficulty: Easy

History lovers will enjoy walking around where Henry David Thoreau famously spent two years living in a cabin in the 1840s. That cabin was in what's now known as the Walden Pond State Reservation. 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. It sings the praises of using nature to forge meaningful connections among the physical and spiritual worlds.

The site, in all its glory, is marked by granite bollards. Stones mark where the woodshed and other home features once stood, and a sign proclaims one of the book's most quotable snippets.

A two-mile loop trail skirts the edges of Walden Pond, taking a few detours deeper into the woods — including one to a replica of Thoreau's cabin — along the way. Consider flipping through a copy of "Walden" before setting out on this journey.

Borderland State Park Loop

Where: Borderland State Park in Easton and Sharon

Total distance: 8.5 miles

Difficulty: Moderate

Plenty of people go to Borderland State Park to tour its palatial, ivy-covered stone mansion, which dates back to 1910. Others go with the intention of playing tennis or disc golf or fishing in the pond, but the park's hiking trails are also a highlight.

Borderland is true to its name for several reasons. Not only does the park sit on the actual border of Sharon and Easton, but it also separates the gentle hills in the north from the flatter land in the south. Historically, it once divided the territory of Native American tribes as well. Take in as much of the land as possible by combining hiking trails to form a figure eight around the park. This DIY "loop" includes the 2.9-mile Pond Walk as well as portions of the Northwest, New England Mountain Bike Association (NEMBA), Ridge, Friends, and Granite Hills trails and Quarry and Morse loops.

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 8.5-mile journey to see some of them, plus a filming location for the movie "Shutter Island."

Related: 10 Charming Small Towns to Visit in Massachusetts

Peddocks Island

Where: Boston Harbor Islands National Recreation Area

Total distance: About five miles

Difficulty: Easy

Peddocks Island is accessible only via ferry from the Greater Boston town of Hingham, which makes it feel remote. Part of the Boston Harbor Islands National Recreation Area, it is one of the largest islands in the harbor. A hike around this curving hunk of land takes you through forests, along the scenic shoreline, and through the paved paths of Fort Andrews, a military outpost that dates from 1900. Along the walk, hikers are likely to see an array of wildlife as well as remnants of the island's fascinating history.

Many people have called the island home over the years, from Portuguese fishermen to World War II prisoners of war. The island harbors plenty of secrets, too, like long-ago drunken parties in a notorious inn and bootleggers stashing bottles in Peddocks' coves. A walk around the island only skims the surface.

Wompatuck State Park Loop

Where: Wompatuck State Park in Hingham

Total distance: About 10 miles

Difficulty: Moderate to challenging

Wompatuck State Park, lovingly called "Wompy" by locals, stretches across 3,526 acres, covering a large swath of Hingham and parts of Cohasset, Norwell, and Scituate. The land was historically used by a Native American tribe and much later became a naval ammunition depot. Concrete bunkers were built there to store munitions, but the depot was deactivated in the 1960s. The bunkers, however, are still visible to park visitors. One such bunker, called N-9, was renovated by three Eagle scouts in 2008. It's now covered in colorful graffiti. Make your way around the park, hopping from trail to trail to create your own 10(ish)-mile loop. You'll see the bunkers and meander through peaceful woods and meadows on your adventure in Wompatuck.

Noanet Peak

Where: Noanet Woodlands in Dover

Total distance: About two miles out and back or a three-mile loop

Difficulty: Easy

A 25-mile drive from Boston, Noanet Woodlands lure city dwellers in search of tranquil forest walks. But Dover locals know its 30-car parking lot can fill up in no time during spring and fall when the hiking is best. Aim to arrive early in the morning or in the evening, especially in the summer when days are long.

The reward is a reasonably easy climb to Noanet Peak, a rocky ledge with lovely views. On a clear day, you can see the Boston skyline to the north. The Noanet Woodlands are especially beautiful during the fall foliage season. The descent is followed by a leisurely stroll past a scenic pond and former mill site.

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