Seven of the best hiking destinations near Boston

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Massachusetts is quintessential New England with its gorgeous coastline, bottomless seafood, and charming Cape Cod style homes and buildings. And the city of Boston might be best known for the die-hard baseball fans of the Red Sox, as well as the historic and cultural attractions but there are plenty of excellent walking and hiking trails in and around the city to suit hikers of every level. The small state of Massachusetts is dotted with hiking trails from coastal strolls to hilltop views. With decent elevation and great views, some gorgeous river walks, and even a couple of mountains, whatever you look for in a hiking vacation you can find here.

Denver might still be able to keep their bragging rights when it comes to convenient hiking near a major city, but Boston might surprise you with just how many spots there are to take in the great outdoors. So if you are cruising from Boston, taking a family vacation, or scoping out the colleges, you’ll want to schedule some time to get outside. Take a break from the urban attractions, the hustle of the city, and get in touch with the natural world in and around Boston. Here are a few of the best hiking destinations near the city.

Best hiking destinations near Boston

Great Blue Hill

With 7,000 acres of rolling green landscape and 125 miles of fantastic trails, the Blue Hills Reservation is likely one of Boston’s best hiking destinations. The reservation is just over 10 miles from Boston’s city center making it very accessible to locals and visitors alike. With that said, expect the trails to be busy during peak times.

Climb to the top of the Great Blue Hill for a relatively short and moderate hike with just over 800 feet elevation gain. Soak in the stunning views of the city skyline, or explore the myriad paths, trails, and walks before the skiers return in the winter.

Just 3 miles up from the road is Houghton’s Pond, a great picnic spot and place to take a dip when the weather is nice enough. So be sure to pack your swimming suits and a change of clothes because nothing is better than a little dip after a brisk hike.

Skyline Trail

Speaking of Houghton’s Pond, next up on our list of best hikes near Boston is the Skyline Trail which starts on Hillside Street in the direction of Houghton’s Pond. As the name suggests, Boston’s Skyline Trail in the Middlesex Fells is one of the best spots to grab uninterrupted views of the city.

The Middlesex Fells Reservation itself offers an array of trekking options with 100 miles of trail, but the Skyline Trail is the pick of the bunch. With seven and a half miles of rough terrain under the shade of wooded forests and around glittering lakes, the trail ascends to 935 feet and offers awesome skyline panoramas along the entire route.

With its stunning views and close proximity to the city center, expect this trail to be crowded on weekends.

Boston skyline

Deer Island

Deer Island is about a 30 minute drive from Boston’s city center. It’s a 2.7 mile loop trail that is suitable for most skill levels. The path is paved and there is very little elevation change. Read perfect for kids, strollers, and wheelchairs. So while this trail might not satisfy an avid hiker’s itch it’s still well worth a stroll and a great excuse to get outside.

Depending on what season you visit you may see wildflowers and wildlife. No matter what time of year you visit, you’ll see incredible views of the ocean and nearby islands.

World’s End Nature Reserve

Although it is one of the smallest nature reserves in the Boston area, there’s plenty to intrigue hikers and outdoor enthusiasts at World’s End. Best of all, it is only 15 miles outside the city so incredibly convenient! Five miles of gentle trails roll their way past Hingham Harbor and offer a delightful array of landscapes including hills, saltwater marshes, and coastline.

It is also a must for birdwatchers, as the forest is absolutely full of native Massachusetts species and one of the best places in the state for twitchers. If you time your trip right you might even be able to take in the blooming wildflowers.

The trails in World’s End are easy to moderate and a great option if you’re traveling with kids. There are 4.5 miles of carriage trails and footpaths throughout the property so while the “trails” are easy to navigate be sure you’re wearing the proper footwear.

World’s End is another great spot to stake a picnic. Bring a blanket and set it up in one of the fields overlooking the water.

To access World’s End there is a small fee, $8 for adults and free for children.

Breakheart Reservation

Breakheart boasts some of the most varied trails to be found near Boston which is why it is a favorite location for almost every style of hiker and walker, as well as being enormously popular with mountain bikers! With seven hills, hardwood forests, and the Saugus River you can stroll gently along the riverbank, enjoy lush wooded trails or take on challenging summits, depending on your tastes, experience, and condition.

With a wide variety of reservations, state parks, and nature reserves within a stone’s throw of the city center, Boston is a surprisingly great choice for a hiking vacation! It might not be quite as dramatic a setting as the mountains of Western Canada but hikers will find plenty to enjoy around Boston.

Moose Hill Wildlife Sanctuary

The Massachusetts Audubon Society is just a 30 minute drive from Boston’s city center. It is Massachusetts’ largest nature conservation nonprofit with more than 40,000 acres of land dedicated to saving birds and other wildlife. The property is home to coastal landscapes, beautiful hilltop views, green fields, wooded trails, and old farms.

A hike on Moose Hill will have you passing through trails with views of a fire tower, old barns, stone walls, and flowing streams. The climax is the view at Bluff Overlook, a rocky ledge with aerial forest views, and a peak at Gillette Stadium.

If you are traveling with your dog be sure to note that the Audubon society does not allow pets to safeguard the conservation efforts.

State Forest Road and Charley's Loop

If you’re willing to venture out a bit further, Purgatory Chasm State Reservation is about an hour's drive from Boston’s city center and well worth the trip. It’s classified as a natural landmark by the state and rightfully boasts its recognition.

This particular hike is a short 3.2 mile loop. Charley’s loop portion is just 1.7 miles and will take you between 70 feet granite walls. Here you’ll see unique rock formations such as The Pulpit, The Corn Crib, The Coffin, Lovers' Leap and Fat Man's Misery. Keep an eye above and you might see climbers making their way to the top of the rocks.

Both trails are very popular on the weekends and after work hours so be sure to plan accordingly if you want to avoid the crowds.

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