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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

Buffumville Lake (Group Shelters)

Charlton, Massachusetts

Buffumville Lake (Group Shelters)

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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