Hiking in Massachusetts is spectacular in any season, but it’s hard to deny there’s something special about hitting the trails in the fall. The spectacular foliage and the crisp fall air make for a truly awesome time to explore the wilds. Check out these short and sweet fall hikes that won’t take you all day but still offer some amazing views. They’re some of the best hikes in Massachusetts!

1. Wachusett Mountain West Side Trail, Wachusett Mountain
Mount Wachusett, Princeton, MA 01541, USA
Flickr/gGraphy
First on the list of the best hikes in Massachusetts that are perfect for fall is Wachusett Mountain West Side Trail. Try this quick loop trail on Wachusett Mountain near Westminster for a fun and easy fall hike. The trail is only 2.7 miles round trip and will take you through groves full of copper-hued leaves and past scenic overlooks. It’s a great place to appreciate the beauty of the season.
2. Pond Trail, Tully Mountain, Royalston
Tully Mountain, Orange, MA 01364, USA
AllTrails/Michelle Ann
Tully Mountain is a gorgeous peak in central Massachusetts. It’s also home to Tully Pond, a quiet and scenic little spot that offers surprisingly dramatic views of Doane’s Falls. The hike around the pond is level and quick, perfect for a day hike or family outing.
3. Caryl Trail at Noanet Woodlands, Dover
Noanet Woodlands, Powisset St, Dover, MA 02030, USA
Yelp/Karen W.
The Noanet Woodlands in Dover offers over 17 miles of trails for all experience levels, but the Caryl Trail is a short and sweet hike that’s perfect for casual hikers. It's also a great kid-friendly hike around Massachusetts. The trail extends for about a half-mile and will deliver you to a charming old mill site ringed by lovely fall color. Learn more about Noanet Woodlands.
4. Skyline Trail at Middlesex Fells Reservation, Stoneham
Middlesex Fells Reservation, 4 Woodland Rd, Stoneham, MA 02180, USA
Flickr/Niklas Tenhaef
The Middlesex Fells Reservation Skyline Trail will reward you with a gorgeous view of the Boston skyline (get it?), complete with stunning fall foliage.The trail is just under seven miles and perfect for an afternoon hike and picnic combo. Check out more about Middlesex Fells Reservation.
5. Monument Mountain Trail, Monument Mountain, Great Barrington
Monument Mountain Reservation, Great Barrington, MA 01230, USA
Tripadvisor/dibird50
This lovely 2.8-mile loop trail is offers gorgeous views of the Housatonic River Valley and the southern Berkshires. You’ll encounter a few steep bits, but for the most part the trail is an easygoing amble up and down the mountain. Find out more about Monument Mountain.

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6. Mass Audubon’s Ipswich River Wildlife Sanctuary, Topsfield
Mass Audubon's Ipswich River Wildlife Sanctuary, 87 Perkins Row, Topsfield, MA 01983, USA
Yelp/Steph J.
This 1,954-acre wildlife sanctuary offers 12 trails to choose from, so you’ll be spoilt for choice as you explore the gorgeous fall woods. If you’re feeling extra adventurous and are a Mass Audubon member, you can rent a canoe and paddle around the marshes of Ipswich River. See more about Ipswich River Wildlife Sanctuary.
7. Mount Norwottuck and Horse Caves Trails, Mount Holyoke State Park
Mount Holyoke Range State Park, 1500 West St, Amherst, MA 01002, USA
Flickr/Paul Cooper
These trails may be short but they pack a lot of punch. The Mount Norwottuck trail is just 3.2 miles, but will take you to the summit of the mountain. The Horse Caves trail will bring you to a series of ledges that have amazing views of the foliage. We bet you'll agree that is one of the most scenic hikes in Massachusetts. Read more about hiking at Mount Holyoke State Park.
8. Birch Pond, Saugus
Birch Pond Drive, Birch Pond Dr, Saugus, MA 01906, USA
Flickr/MOTT
This is the ultimate quick and easy hike. Birch Pond is part of the Lynn Woods Reservation and can be reached via a pleasant 4.4-mile loop trail OR via a quick walk from the road on the other side of the reservation. Either way, once you're there you'll want to walk around the pond and admire the reflection of the foliage in the clear water. Check out more about Birch Pond.
9. The Gardens at Elm Bank, Wellesley
Massachusetts Horticultural Society - Garden at Elm Bank, 900 Washington St, Wellesley, MA 02482, USA
Facebook/Massachusetts Horticultural Society
If you're looking for more of a walk than a hike, The Gardens at Elm Bank is the perfect spot to wander. With 35 acres of woodlands, meadows, fields and gardens to discover and plenty of winding paths to explore, you'll be sure to find a pretty fall scene around every corner. Find out more about The Gardens at Elm Bank.
10. Silver Lake Loop Trail, Breakheart Reservation, Saugus
West Silver Lake Loop Road, W Silver Lake Loop Rd, Laona, WI 54541, USA
Yelp/Galina M.
When waterfront views are involved, it's hard to go wrong. Read more about Breakheart Reservation.

For more stunning hikes to try, check out our list of great hikes under 5 miles in Massachusetts that everyone should try.

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More to Explore

Best Hikes In Massachusetts

Danielle Schwartz | July 29, 2022

What are the best kid-friendly hikes in Massachusetts?

When you're out in nature with the little ones, you'll want to pick hikes that they can do as well as you can for maximal fun. These kid-friendly hikes in Massachusetts are all one mile and under, so you can head out worry-free and know that you'll all be able to have a great time together. If you're waterfall fans, head to Chapel Brook Falls Trail in Ashfield. It's only half a mile long and you'll get to check out a pretty water feature. Fort Hill Trail in Eastham is one mile long and features gorgeous views of the ocean from Cape Cod National Seashore.

What are the easiest hikes in Massachusetts?

If you're traveling with older kids or just with other adults, you can kick it up a notch to hike trails that are 5 miles or less in length. Some of the easiest hikes in Massachusetts are also the most scenic. Bash Bish Falls at Mount Washington is only about a mile long, and you'll find a waterfall and gorgeous swimming hole that you'll want to spend the whole afternoon enjoying. If you like long walks with views for miles around, make your way to Hulbert's Hill in Batholomew's Cobbie in Sheffield for a 5-mile-long trail through endless greenery.

What is the best wildflower hike in Massachusetts?

If you're hiking in the spring, you'll definitely want to take the opportunity to see the best wildflower hike in Massachusetts, the Mount Norwottuck Trail. You'll find this bright and cheerful trail in the Mount Holyoke Range State Park near Amherst. The trail is 3.4 miles long and features some of the prettiest blooms in the state. It's also a great place to go for bird watching. The idyllic springtime getaway is definitely here.

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