Hiking in Massachusetts: 8 Trekking Spots for Adventure Seekers


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Posted by Geraldine Mills, guest blogger of Australia

Massachusetts has a rich history and an impressive background that always makes for an interesting story. There are a lot of fun facts about this state that you probably didn’t know. For example, Massachusetts is where both the Toll House cookie and basketball originated. It’s also where the first branch of Dunkin’ Donuts  made its way into the American lifestyle.

Massachusetts has plenty of deciduous forests with a lot of rolling hills. If you’re looking for some adventure, you should go on a hike and enjoy Massachusetts’ natural scenery. Massachusetts is a great place to get in touch with nature, so you should do an activity that lets you do just that.

If you plan on going on a hike, here are eight of the best trekking spots that Massachusetts has to offer:

Skyline Loop Trail

If you’re in Middlesex County looking for a hike near the city, consider stopping by the town of Stoneham. There you’ll be able to find the Middlesex Fells Reservation, also known as the Fells.

In the Fells, you can do all sorts of recreational activities. This includes trekking one of their many hiking trails.

One of the best and most popular hiking trails in the Fells is the Skyline Loop Trail that spans about 7.6 miles or 12.2 km. This hike is of moderate difficult.  Although it won’t be that hard, you still need to keep your guard up. Despite being so close to the city, the tree-covered path still feels like a small sanctuary.

Mount Greylock State Reservation

Mount Greylock State Reservation is home to Mount Greylock, which is the highest point in the state.

Standing 3,491 feet tall, plenty of hikers are interested in getting up to the top of the peak. If you want to make use of their campsite, there is a nightly charge, and you can only access them by hiking.

Since you’re hiking a considerable height, you should make sure that you bring trekking poles. You’re going to appreciate the fact that you brought them with you because the descent can be tricky.

Blue Hills Reservation

Another reservation in Massachusetts that offers a variety of hiking trails is the Blue Hills Reservation. The Blue Hills Reservation is home to the Great Blue Hill, which stands at about 635 feet. You’ll reach the peak of Great Blue Hill by going through one of their 51 or so hiking trails.

By going to the three-mile Skyline Loop hiking trail, you’ll be able to get to the Great Blue Hill peak. This can take between one hour and three hours, depending on your pace. However, do note that this hiking trail is quite challenging.

Once you’re at the peak, you can find the Eliot Observation Tower. This will give you an even better panoramic view atop the Great Blue Hill.

Emerald Necklace

The country’s first landscape architect, Frederick Law Olmsted, wanted to create a park system that weaves through Boston. He wanted it to serve as a sanctuary away from city life, which he successfully did. After all, he managed to create the park system that Bostonians now know of as the Emerald Necklace.

You can try a looped hiking trail if you want to get the full experience that the Emerald Necklace can give you. It’s moderately difficult, especially since this trail spans about 32 miles or 52 km.

If you’re in Boston and want a little getaway from the bustling city, you may consider hiking at the Emerald Necklace.

Acorn Trail

For a more comfortable hiking trail than some of the ones we’ve mentioned in this article, you should stop by the Great Brook Farm State Park in Carlisle. You can enjoy hiking the Acorn Trail that a lot of locals love since it’s short and easy to finish.

The trail itself spans about three miles or 4.8 km overall. It’s split into three sections: Acorn North, Acorn Trail, and Acorn South. Although it is a short trail, you can finish it faster by hiking the main Acorn Trail.

Charley’s Loop Trail

Purgatory Chasm State Reservation in the town of Sutton certainly has a very intimidating name. The reason behind the name is its 25-mile long (or 40 km) 70-feet deep gorge of granite bedrock. Nonetheless, this is one of the famous sites in the state.

In this unique, geologic nature reserve lies Charley’s Loop Trail that takes you on an exciting tour and view of the ravine itself. It covers around 1.9 miles or three kilometres. This trail is best for people who are looking for a moderate to strenuous hiking trail challenge.

Cape Cod Rail Trail

The Cape Cod Rail Trail’s original use was to be a train track that would connect Cape Cod to Boston. Therefore, if you hike this trail, you’d pass through about six towns on Cape Cod during the 22-mile hike.

Appalachian Trail

Last but not least is the famous Appalachian Trail, which is the world’s longest hiking trail.

The Appalachian Trail is undoubtedly an undertaking that only expert hikers should try out. After all, this is a hiking trail that covers 14 states. Overall, the trail is about 2,175 miles or around 3,500 km.

If you’re looking to go on a full-on adventure that has you on the road for more than a couple of months, take on the behemoth that is the Appalachian Trail.


Massachusetts has many hiking trails and reservations that make for a beautiful adventure. More so, if you want to reconnect with nature.

From one of the most iconic hiking trail in the world to a green sanctuary in the middle of the city, there are plenty of hiking trails worth trying out for all hikers.

If you find yourself in Massachusetts or are planning to be there anytime soon, consider hiking these eight trekking spots!

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