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

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

Charlton, Massachusetts

Buffumville Lake (Group Shelters)

Bourne, Massachusetts

Oceanview Buzzards Bay Getaway

From $112 / night

Bourne, Massachusetts

Waterfront Home with Bay Views & Private Pool!

From $252 / night

Guides and stories

5 Tips for Finding Beautiful Fall Foliage in Massachusetts

Gustavo Quiros

Quick links