Outbound Collective logo

Top Spots

Dolan Center Launch to Town Landing Lane

Dedham, Massachusetts

1.6 mi / 141 ft gain

Hike the Wilson Mountain Reservation Trail

Dedham, Massachusetts

4.0
2 mi

Lowell Woods and Sandy Valley Loop

Westwood, Massachusetts

3.91 mi / 272 ft gain

Millennium Park

Boston, Massachusetts

3.7 mi / 226 ft gain

North and South Skyline Trail

Canton, Massachusetts

8.33 mi / 1463 ft gain

North Skyline Trail to Skyline Trail South Loop via Coon Hollow Path

Milton, Massachusetts

4.51 mi / 814 ft gain

Wolcott Path and Puddle Path to Hemenway Hill

Milton, Massachusetts

2.85 mi / 423 ft gain

Wolcott Path to Eliot Tower

Milton, Massachusetts

2.22 mi / 410 ft gain

Blue Hills Trail to Elliot tower

Milton, Massachusetts

1.87 mi / 495 ft gain

Places to stay

West Hill Park

Northbridge, Massachusetts

West Hill Park

Boston / Cape Cod KOA Holiday

Middleborough, Massachusetts

Boston / Cape Cod KOA Holiday

Buffumville Lake (Group Shelters)

Charlton, Massachusetts

Buffumville Lake (Group Shelters)

Normanton Farms

Litchfield, New Hampshire

Normanton Farms

From $100 / night

West Thompson Lake Campground

Thompson, Connecticut

West Thompson Lake Campground

Souhegan Serenade

Souhegan Serenade

From $150 / 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