The Best Leaf-Peeping Hikes Near Boston

It’s the most wonderful time of the year in Boston. With the crisp fall season and all the apple treats that come with it, the region makes autumn even better by delivering a vibrant display of stunning New England foliage.

Sometimes the best way to take in the array of colors and enjoy the comfortable temperature drop means getting to a higher altitude. So we’ve rounded up the best hiking destinations that will fulfill your fall dreams while getting your steps in. The hikes range from easily accessible to more on the challenging side, so keep reading to find out which hiking trail near Boston you should find yourself exploring this season.

A little over five miles from Boston, this worthwhile hiking destination has prime leaf-peeping sights without having to go the distance. In fact, you can take the orange line to Oak Grove station, and it’s only a 10-15 minute walk from there. Take your pick from a number of trails including the Skyline loop, which, you guessed it, provides views of the city’s skyline. But if you’re looking for something less intense (since the Skyline is about an 8-mile loop), you can always take one of the trails that goes along Spot Pond.
Distance from Boston: 10 minutes

Marigold Marsh on a cloudy day

Another option that’s extremely close to the city, Blue Hills Reservation provides an oasis that’s totally within reach for those looking to get some steps in via greater Boston’s finest fall treks. With more than 125 miles of trails, Blue Hills is ideal for just about every type of hiker. From the less challenging Houghton’s Pond, a mile loop around the water, to the Great Blue Hill, a strenuous but popular hike that takes you to the historic Eliot Observation Tower, a 35-foot structure built nearly a century ago, you’ll have your fair share of walks to map out.
Distance from Boston: 20 minutes

World's End Reservation

Hop on the ferry over to Hingham for a chance to embark on the paths of World’s End, featuring more than four miles of tree-lined trails serving up views of the Weir River, Boston Harbor, and topped off with the city’s skyline. Not only do you have your choice of paths to take, but World’s End also offers guided bird walks throughout “Bird Alley,” kayak tours, and Sunset Hike and Sip and Full Moon hikes. While you’re there, you can also visit one of the last family farms in Hingham, Weir River Farm, as they’re known for lively events, animals, and a wholesome farm store.
Distance from Boston: 40 minutes

ducks on pond

This wildlife sanctuary doubles as a worthwhile hiking spot, featuring nine miles of trails including a quarter-mile-long boardwalk that accommodates wheelchairs, strollers, and walkers. While a shorter path, you can still enjoy views nestled inside the marsh and you may come across some forest creatures along the way like otters, turtles, and a wide range of bird species. What’s more, the sanctuary is only a five-minute drive from Natick’s Lookout Farm, equipped with a taproom, restaurant, and of course, some of the best apple picking near Boston. Consider your fall-themed weekend plans set.
Distance from Boston: 35 minutes

ancient glacial stones at Purgatory Chasm

This isn’t your average fall hiking trip. Within this park, you’ll find two miles of rocky terrain said to date back as old as the last Ice Age. Rise to the challenge of meandering through caves and over a variety of ancient rock formations like the uniquely named Corn Crib, Lovers’ Leap, and Fat Man’s Misery. If you’re not keen on that idea, you can always enjoy the sights safely from the park’s open field and picnic area.
Distance from Boston: 50 minutes

Rockport granite quarry

Located within the seaside town of Rockport, on a clear day, this state park offers up views of Maine’s Mount Agamenticus plus the Isles of Shoals off the coast of New Hampshire. Within the park, there’s an approachable 1.6-mile loop trail that takes you throughout the woods and toward the ocean so you can take in the changing leaves beside its serene backdrop. When you’ve gotten enough fresh air in, there are more than enough quaint shops and restaurants nearby to explore.
Distance from Boston: 55 minutes

lake surrounded by trees

Brace yourself for the fall foliage at this next hiking destination. At Mount Holyoke’s peak, you’ll look out to miles and miles of colorful treetops and rolling hills. Even better, you can take the drive up to the summit if you’re looking to make leaf-peeping easier. But once you’ve reached the highest point, it’s recommended you take in the sights from the historic Summit House’s wrap-around porch for a complete 360-degree view.
Distance from Boston: 1 hour and 30 minutes

top of monument mountain

Great Barrington
Great Barrington alone is a prime seasonal spot, in fact, really anywhere within the Berkshires is fit for fall. But in Great Barrington, you’ll find a bustling downtown and cultural district nestled within the hills—and not far from that strip, there’s of course Monument Mountain Reservation. From its 1,642-foot summit, you’ll be able to see the Housatonic River Valley, which has inspired arts and literature for centuries, including Moby Dick. Who would’ve thought?
Distance from Boston: 2 hours

pond surrounded by forest

Also nestled within the Berkshires, Pleasant Valley Wildlife Sanctuary is yet another spot that grants you up close and personal access to New England’s famous foliage and some of the area’s popular animals. The trails here, set along Lenox Mountain, wind through its lush meadows and vibrant forest, including the universally accessible flat trail around Pike’s Pond, path around the beaver ponds, and of course, the 850-foot hike to the top of the mountain.
Distance from Boston: 2 hours and 10 minutes

changing color leaves on Clark campus

This location might require going the distance but once you’ve made it to the Clark Art Institute, you’ll likely be planning your trip back as fall is known to be one of the best times to visit the campus. Set against another breathtaking Berkshires backdrop, the Clark provides a modern take on an outdoor adventure, with trails featuring art installations and an upward climb to Stone Hill, which leads you to two small galleries inside its “sanctuary in the woods,” a.k.a. Lunder Center.
Distance from Boston: 2 hours and 45 minutes

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Jillian Hammell is a contributor for Thrillist. You can follow her on Instagram.

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