6 Great Hikes Outside of Boston

From walking to running and hiking to biking, active residents of Forest Properties in Boston will find plenty of nearby trails to keep themselves moving every season. If you’re looking to disappear into nature without spending a good part of your day in the car, here are 6 great hiking trails near Boston.

woman wearing a rainbow shirt and a hiking backpack.

1. Spectacle Island

Located just 4 miles from downtown Boston is Spectacle Island, which is a 105-acre island that is surrounded by the Boston Harbor Islands. Besides hosting beautiful panoramic views around every curve of its hiking paths, visitors may spot city views of Boston from the tallest hill on Spectacle Island. Now it makes sense why the name is so fitting!

2. Great Blue Hill at Blue Hills Reservation

Expanding over 7,000 acres and 125 miles of hiking trails with a range of terrain, Great Blue Hill in Milton, Massachusetts is an awesome destination for your next hike.

Not only is it Great Blue Hill 18 miles south of Boston (which is convenient for Landing 53 residents), it’s the highest peak in the Blue Hills Reservation and highest summit that sits south of Main near the Atlantic Ocean. Whichever hiking trail you choose to explore, you’re bound to make plenty of stops for photo ops. One of our favorites is the Red Dot Trail, which is a moderate challenge that expands 2 miles round-trip.

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3. The Freedom Trail

For an urban hike, check out one of the country’s most-love city walks: The Freedom Trail. This 3-mile pathway is marked by a line of red bricks that takes visitors to 16 historic monuments and sites in the heart of Boston. Here are a few to keep your eyes open for:

  • Site of the Boston Massacre
  • The Old South Meeting House
  • Old Granary Burying Ground
  • Paul Revere’s house
  • The Old North Church

Besides its location and convenience, residents of The Parkside are only 10 minutes away from the Freedom Trail Visitor Center in Boston Commons. This is a great place to start off your weekend morning walk and head back to your apartment pool to cool off afterwards.

a hiker retrieving his camera from his blue backpack.

4. Skyline Trail at Middlesex Fells Reservation

If there’s one hiking trail we find ourselves recommending again and again to experienced hikers, it’s the Skyline Trail at Middlesex Fells Reservation. This attraction tends to gather serious hikers who are looking for a challenging route that’s filled with rocky terrain, climbing up and down hills, and of course taking a break to soak up stunning views.

Good to Know: The Skyline Trail is 7 miles long and passes through wooded forests, so plan to spend about five hours during your hike and come stocked with snacks, bug spray, and water!

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5. Mount Misery

Don’t let the name fool you – Mount Misery in the town of Lincoln, Massachusetts, isn’t as daunting as its name implies. This park sits about 20 miles outside of Boston and covers 227 beautiful acres. Filled to the brim with wildlife, from deer to squirrels and bird species of every kind, Mount Misery is said to be a former favorite spot of Henry David Thoreau.

The paths at Mount Misery are well-marked and easily guide users to breathtaking spots for a picnic or quiet reading time.

charles river bridge surrounded by summer trees and a flowing river.

6. The Charles River Reservation

Did you know both Boston and Cambridge share the Charles River? The Charles River Reservation is a linear park that stretches over 20 miles, meaning there are plenty of hiking, biking, walking, and running trails with beautiful waterfront views. Better yet… the reservation is a quick 12-minute drive from Clearway Apartments!

Whether you’re looking to stay closer to the heart of Boston or are eager to venture off the beaten path, share your favorite hiking trails with fellow Boston residents on Facebook.

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