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Top Spots

North and South Skyline Trail

Canton, Massachusetts

8.33 mi / 1463 ft gain

Francis William Bird Park

Walpole, Massachusetts

2.55 mi / 223 ft gain

Skyline Trail to Elliot Tower and Accord Path

Canton, Massachusetts

2.16 mi / 574 ft gain

Elliot Tower via Skyline Trail

Canton, Massachusetts

1.57 mi / 643 ft gain

Blue Hills Skyline Trail: Route 138 to Willard Street

Canton, Massachusetts

6.64 mi / 1237 ft gain

Hike the Ponkapoag Pond Trail

Randolph, Massachusetts

3.82 mi / 173 ft gain

Ponkapoag North Loop

Milton, Massachusetts

1.89 mi / 220 ft gain

Moose Hill, Bay Circuit, Turkey, Bluff and Billings Loop

Sharon, Massachusetts

3.01 mi / 374 ft gain

Old Summit Road Trail

Sharon, Massachusetts

1.72 mi / 121 ft gain

Places to stay

Boston / Cape Cod KOA Holiday

Middleborough, Massachusetts

Boston / Cape Cod KOA Holiday

West Hill Park

Northbridge, Massachusetts

West Hill Park

Buffumville Lake (Group Shelters)

Charlton, Massachusetts

Buffumville Lake (Group Shelters)

West Thompson Lake Campground

Thompson, Connecticut

West Thompson Lake Campground

Maurolou Farm

Little Compton, Rhode Island

Maurolou Farm

From $150 / night

Spring Hill on Cape Cod Cranberry Farm

Sandwich, Massachusetts

Spring Hill on Cape Cod Cranberry Farm

From $99 / 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