trees and hills in autumn in the Berkshires in Massachusetts

While the Boston area shines uniquely in all four seasons, there’s something magical about the bright colorful leaves, crisp air, and pristine orchards that take over every autumn. Tourists will flock to New England destinations like New Hampshire’s Kancamagus Highway, Maine’s Acadia National Park, and Vermont’s Green Mountains for the autumn fall foliage experience, but there are plenty of stunning opportunities right here in Massachusetts.

From coastal beauty to mountain majesty, Massachusetts provides it all. Walk, drive, or cruise these beautiful Boston-area leaf peeping experiences!

Middlesex Fells Reservation 

autumn view of the Boston skyline from the Middlesex Fells

Just five miles north of Boston, the Fells features more than 100 miles of scenic trails and multiple ponds, making this local state park a perfect place to leaf peep. The Fells spans across Malden, Medford, Melrose, Stoneham, and Winchester — a convenient sightseeing adventure for city-dwelling families.

The Mohawk Trail (Berkshires)

The Mohawk Trail through the Berkshires features amazing fall views combined with the charm of artsy small towns. One recommend route is to start in Williamstown and take the trail (Route 2) east through North Adams. Once you arrive in Charlemont you can take a leaf peeping detour on Route 8A to cross the Bissell Covered Bridge. The town of North Adams also embraces the fall season with its Fall Foliage Festival in October, complete with a parade and family activities. It is also worthwhile to check out nearby historic Greenfield and view colorful leaf backdrops from the lookout at Poet’s Seat Tower and the beautiful views of the Jacob’s Ladder Byway.

The Cape

Scargo Lake on Cap Cod in autumn

Cape Cod wouldn’t usually enter my mind as a spot for fall since I associate it with summer and beaches, but there are some perfect areas to take in the New England foliage without traveling too far. Once you cross over the Sagamore Bridge, you can exit onto Route 6A. This will provide a rural route with twists and turns through the historic town of Sandwich. Travel along Old King’s Highway, which winds around the Cape Cod Bay — you’ll see plenty of picturesque ponds and pastures to take in on your route. If driving isn’t your thing, hop on to the Cape Cod Railway for one of their spectacular scenic train rides! 

Blue Hills Reservation

The Blue Hills feels like the perfect fall retreat — without the hassle of driving far from the city. Its 6,000-acre park covers parts of Quincy, Milton, Braintree, Randolph, Canton, and Dedham. The reservation is well known for its hiking trails, giving both nature and fitness lovers the ability to explore the season while squeezing in some family exercise.

Mass Audubon’s Broadmoor Wildlife Sanctuary

Broadmoor Sanctuary is a beautiful park in Natick and a favorite spot for bird watching. The sanctuary hosts many hiking trails and is located on the Indian Brook and the Charles River. A visit to Broadmoor provides an amazing array of wildlife watching — you can also follow trails to wide open fields and streams. It’s a perfect local score for foliage finders and nature lovers. 

Boston Fall Foliage Cruises

Did you know you can experience the beauty of Boston’s fall foliage from a cruise along the Charles River or the Harbor Islands? These 90-minute sight seeing cruises are a perfect way to go leaf peeping while learning a bit about Boston history!

Battle Road Byway (Route 2A)

Gain a little history as you peep the amazing foliage along the road of the Revolutionary War battles! This byway travels through the towns of Arlington, Lexington, Lincoln, and Concord. The heavily wooded area provides spectacular colors every year without fail.  

Mount Greylock

autumn foliage in the Berkshire hills taken from the Mount Greylock range

Mount Greylock is the highest point in the state at nearly 3,500 feet. The views are endless! Enjoy plenty of scenic overlook stops on your drive to the top.

Looking for even more fall fun in Boston? Try a pumpkin patch, a corn maze, or an apple orchard!

Boston Moms
Boston Moms is a rapidly growing community of moms in the Boston area, providing a collaborative parenting resource written and read by local moms. We are passionate about engaging with our readers online through mom-to-mom content + recommendations, and offline through our exciting local events that connect moms to each other and to local and national businesses they should know about!