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Top Spots

Nahanton Hill via Skyline Trail

Milton, Massachusetts

1.54 mi / 121 ft gain

Kitchamakin Hill and Chickatawbut Hill Loop via Skyline Trail

Braintree, Massachusetts

2.67 mi / 351 ft gain

Quincy Quarries Climbing Trail

Quincy, Massachusetts

0.44 mi / 52 ft gain

Rattlesnake and Wampatuck Hills Trail

Quincy, Massachusetts

1.85 mi / 354 ft gain

Little Dome via Sawcut Notch Path

Quincy, Massachusetts

2.81 mi / 141 ft gain

Buck Hill Path Loop

Milton, Massachusetts

1.28 mi / 115 ft gain

Buck Hill to Hawk Hill Loop

Milton, Massachusetts

3.29 mi / 495 ft gain

Skyline Trail, Headquarters Path, and Sawcut Notch Path

Quincy, Massachusetts

7.24 mi / 1125 ft gain

Hike The Skyline Trail at Blue Hills

Quincy, Massachusetts

4.0
12.7 mi / 2542 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

Normanton Farms

Litchfield, New Hampshire

Normanton Farms

From $100 / night

Buffumville Lake (Group Shelters)

Charlton, Massachusetts

Buffumville Lake (Group Shelters)

Spring Hill on Cape Cod Cranberry Farm

Sandwich, Massachusetts

Spring Hill on Cape Cod Cranberry Farm

From $99 / night

West Thompson Lake Campground

Thompson, Connecticut

West Thompson Lake Campground

Guides and stories

Experience Cape Cod - Dune Shack Trail, Provincetown

Experience Cape Cod - Dune Shack Trail, Provincetown

Shaun Logan

 5 Tips for Finding Beautiful Fall Foliage in Massachusetts

5 Tips for Finding Beautiful Fall Foliage in Massachusetts

Gustavo Quiros

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