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Top Spots

Mount Misery Trail

Sherborn, Massachusetts

3.82 mi / 233 ft gain

Pine Hill Loop

Sherborn, Massachusetts

4.01 mi / 246 ft gain

Rocky Narrows Overlook Loop

Sherborn, Massachusetts

2.64 mi / 269 ft gain

Sherborn Red Trail

Sherborn, Massachusetts

4.1 mi / 374 ft gain

Audubon Boardwalk and Glacial Hill Loop

Natick, Massachusetts

3.54 mi / 243 ft gain

Broadmoor Loop

Natick, Massachusetts

1.25 mi / 144 ft gain

South Street Double Loop

Natick, Massachusetts

1.99 mi / 98 ft gain

Priory Double Loop

Dover, Massachusetts

2.7 mi / 390 ft gain

Chase Woodlands and Peters Reservation Loop

Dover, Massachusetts

2.97 mi / 394 ft gain

Places to stay

West Hill Park

Northbridge, Massachusetts

West Hill Park

Buffumville Lake (Group Shelters)

Charlton, Massachusetts

Buffumville Lake (Group Shelters)

Boston / Cape Cod KOA Holiday

Middleborough, Massachusetts

Boston / Cape Cod KOA Holiday

West Thompson Lake Campground

Thompson, Connecticut

West Thompson Lake Campground

Westville Recreation Area

Sturbridge, Massachusetts

Westville Recreation Area

Normanton Farms

Litchfield, New Hampshire

Normanton Farms

From $100 / night

Guides and stories

 5 Tips for Finding Beautiful Fall Foliage in Massachusetts

5 Tips for Finding Beautiful Fall Foliage in Massachusetts

Gustavo Quiros

Quick links