Massachusetts incorporates everything that is quintessentially New England, from the shore to the quaint towns all the way to the rugged forested interior.
The state is the perfect place for the hiker that doesn’t want to wander a complete world away from civilization, but does want to be far enough from the big cities to be immersed in all the Mother Nature has to offer. From meandering beachside trails to trekking up mountains, you can enjoy both in Massachusetts, sometimes even on the same day.
If you are looking to see some of Massachusetts’ finest sights, you will have to hoof it a little, but the rewards in store for hikers are endless.
Skyline Loop Trail
While there are over 125 miles of trails weaving around the small mountains of the Blue Hills Reservation, the Skyline Loop offers the most rewards for only a minimal amount of work.
While only three miles long, the Skyline Loop Trail shows off some of the small summits of the park, wandering up to a number of little mountains on the loop while passing highlights like the Eliot Observation Tower.
OK, the mountains may be small in size, but they lend enough height for tall structures like the Eliot Observation Tower which gets panoramic views over nearby Boston.
Rock Circuit Trail
Snaking its way through the stony hills of the Middlesex Fells Reservation, the Rock Circuit Trail is the perfect mix of thigh-burning workout and scenic sight-seeing trip. While only a 4.7-mile trek through dense forest, the trail itself winds ever-upwards as you push into a steep rocky crag.
However, around every bend in this challenging trail are vantage points that feature sweeping views over downtown Boston, Revere Beach, and Melrose. As it is so close to the city, the Middlesex Fells is a beloved escape for city folks, but the challenge of this trail isn’t for the couch potatoes.
Mount Greylock / Appalachian Trail
There are a number of ways to get to the top of Mount Greylock and even more reasons to make the trip. However, instead of lazing your way up the mountain on the 8-mile drive, why not make the trek on foot instead?
As the tallest peak in Massachusetts, Mount Greylock rises 3,491 feet over the long swathe of uninterrupted forest that surrounds it. At the top sits the Veteran’s War Memorial Tower, a structure that is part amazing lighthouse and part fantasy wizard tower, making the visit to the top a must while in the state.
For those that choose to take the hike up, the best way to the top is actually hike the rugged length of the Appalachian Trail that travels up to the summit and goes right back down on the other side as it continues on its way up to Maine.
Cape Cod Rail Trail
The most rugged trail in Massachusetts the Cape Cod Rail Trail is not. However, this trail traces the iconic cape as it wanders the 22-mile route that used to be a railroad.
In the past, the now-defunct railroad tracks used to be the only route that connected the isolated Cape Cod to Boston. Today, there are many routes that connect the two beloved areas, but no one expected this rail-trail to still be one of them.
The tracks have been removed and the trail has now been paved. Today everyone from hikers, bikers, joggers, and even horseback riders come to tackle the entire 22 miles or just a short slice of it.
While the trail passes through Dennis, Harwich, Brewster, Orleans, Eastham, and Wellfleet, the best part is that while you are hiking through the forest and the occasional scrubland, you are never more than a short walk from a beach.
Purgatory Chasm Trail
Although it is one of the shortest trails in Massachusetts, the Purgatory Chasm Trail is easily the state’s most famous trail. The three-mile loop takes people deep into this unique natural landmark.
Purgatory Chasm gets its name for the quarter-mile long chasm that runs between seventy feet of split granite that cracked from the glacial melt during the last Ice Age. While the chasm is the showpiece, it is not the only thing to see along this trail.
Other areas of the trail not only feature a number of scrambling sections up boulders that entice picnickers and rock climbers alike, but the trail leads to a number of named rock formations like The Corn Crib, The Coffin, The Pulpit, Lover’s Leap, and Fat Man’s Misery.
While visitors can actually slip into certain areas of the chasm and smaller chasms in the granite around it, visitors should be aware that you need to be relatively thin to make it through. Those who have amassed a decent beer gut best work on sucking it in unless they want to get stuck halfway through on their adventure.