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

12.7 mi / 2542 ft gain

Places to stay

Middleborough, Massachusetts

Boston / Cape Cod KOA Holiday

Northbridge, Massachusetts

West Hill Park

41.94403308,-70.60108626, Massachusetts

Waterfront Wonder with Bay Views, Steps to Beach

From $121 / night

Bourne, Massachusetts

Waterfront Home with Bay Views & Private Pool!

From $252 / night

Bourne, Massachusetts

Spacious Wooded Retreat w/ Deck & Alfresco Dining

From $132 / night

Bourne, Massachusetts

Private Pool on the Canal w/ Bourne Bridge View

From $206 / night

Guides and stories

Experience Cape Cod - Dune Shack Trail, Provincetown

Shaun Logan

5 Tips for Finding Beautiful Fall Foliage in Massachusetts

Gustavo Quiros

Quick links