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Discover the best hiking trails in Massachusetts

Escape the city to explore breath-taking hiking trails

While being told to ‘take a hike’ is not always the most endearing advice, with hundreds of diverse hiking trails in Massachusetts, this is advice for locals and visitors to take seriously.

Escape the busy city for a bit of exploration navigating through trails to discover breath-taking landscape, engage in a challenging workout or roam historical grounds.

Massachusetts is lined with trails to suit any hiker’s needs. Matthew Sisk, Deputy Commissioner of Massachusetts’s Department of Conservation and Recreation, recognizes how the state’s hiking trails attract people seeking varying hiking experiences.  “Being outside and recreating is great because it combines exercise with mental stimulation and being in tune with nature, which is just as important,” Sisk said.

So, throw on a pair of sneakers, grab a water bottle and embark along some of the best hiking trails in Massachusetts.












Hiking with History at Great Barrington’s Monument Mountain

Travel up the trails of Monument Mountain and get inspired by the rich artistic history surrounding every corner and cave. In addition to receiving its namesake from a 1800s poem by William Cullen Bryant, Monument Mountain is honored as the birthplace of significant inspiration for the world-renowned novel, Moby Dick by Herman Melville. Try and spot the cave where Melville discussed these ideas with Nathaniel Hawthorne in 1850, all while enjoying views of the Berkshires and Housatonic River Valley.

Break a Sweat on the Rock Circuit Trail

Tucked in the eastern district of the Middlesex Fells Reservation, Rock Circuit Trail is the ideal combination of an unrelenting work out and unique sightseeing. Trek through the 4.7-mile forested trail and push beyond the steep, rocky crag. Adventure around windy paths to reach vantage points for a quick rest with incredible views of downtown Boston, Revere Beach, Melrose and Middlesex Fell’s western district. Completing the challenge of hiking such a rocky trail is well worth the stunning sights waiting at the finish.

The Must-See Mount Greylock

There is no better place to view the beautiful landscape of the Berkshires than from the very top.

“I definitely recommend Mount Greylock. It’s a 13 mile climb and the view at the top is stunning, absolutely stunning,” Sisk said.

Gaze 60 miles out from the top of Mount Greylock at 3,491 feet, the highest point in Massachusetts. Follow one of four summit hikes and be rewarded with stunning panoramic views.

Family Fun at Cape Cod National Seashore

Breathe in the crisp, salty air while enjoying views of the Atlantic Ocean on a guided hike along the Cape Cod National Seashore. Bring the kids along to learn from the rangers and try to spot plants and animals among the diverse environment. Walk along the eastern shore of Cape Cod and admire lighthouses, wild cranberry bogs, marshes and, of course, sandy beaches.

-By Ettractions Digital Content Editor, KATHRYN DUGGAN

Recommended Fun!


Massachusetts: Boston

Other States: Connecticut Maine New Hampshire Rhode Island Vermont

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