Outbound Collective logo

Top Spots

Red, Blue, and Green Loop

Westport, Massachusetts

1.41 mi / 72 ft gain

Old Harbor Yellow, Blue, Green, and Red Loop

Westport, Massachusetts

1.55 mi / 115 ft gain

Dunhams Brook Conservation Area Long Loop

Westport, Massachusetts

2.81 mi / 141 ft gain

Hike Gooseberry Island

Westport, Massachusetts

1.5 mi / 36 ft gain

Gooseberry Neck

Westport, Massachusetts

1.54 mi / 23 ft gain

Beach Trail

Westport, Massachusetts

1.32 mi / 33 ft gain

Quansett and Fresh Pond Trails

Westport, Massachusetts

1.86 mi / 79 ft gain

Herb Hadfield Red, Blue, Yellow, and Gene Loop

Westport, Massachusetts

1.94 mi / 49 ft gain

Westport River (East Branch): Hix Bridge to Head of Westport

Westport, Massachusetts

10.16 mi / 233 ft gain

Places to stay

Maurolou Farm

Little Compton, Rhode Island

Maurolou Farm

From $150 / night

AutoCamp Cape Cod

Falmouth, Massachusetts

AutoCamp Cape Cod

From $129 / night

Boston / Cape Cod KOA Holiday

Middleborough, Massachusetts

Boston / Cape Cod KOA Holiday

Spring Hill on Cape Cod Cranberry Farm

Sandwich, Massachusetts

Spring Hill on Cape Cod Cranberry Farm

From $99 / night

Mystic KOA Holiday

North Stonington, Connecticut

Mystic KOA Holiday

Running Spring Farm

Ledyard, Connecticut

Running Spring Farm

From $110 / night

Guides and stories

My Letter To The Ocean

My Letter To The Ocean

Shaun Logan

Quick links