All Trails

All Difficulties
All Towns
All Organizations
All Water Types
277 trails found

Webster’s Wilderness

Easy Marshfield Dog friendly Parking

Located in Hingham, Webster’s Wilderness is a 244 acre property with natural wetland habitats. This trail system offers a pleasant recreational experience. Overlooking Hingham Bay, it is formed by two…

Webster’s Wilderness

Weir River Farm

Moderate Hingham Parking

Weir River Farmshowcasing historic significance. This trail system offers a pleasant recreational experience. There is something permanently amazing about a big red barn, farm animals, and old stone walls. Visitors…

Weir River Farm

Weir River Woods

Moderate Hull Dog friendly Parking

Located in Hingham, Weir River Woodsthrough beautiful woodland. The 2. 7 mile trail is perfect for hiking. 7 miles of trails through a genuinely dramatic landscape of rocky outcroppings and…

Wessagusset Wetland and Woodland

Easy Weymouth Dog friendly Parking

Located in Weston, Wessagusset Wetland and Woodlandwith natural wetland habitats. This trail system is perfect for hiking. The colony of Wessagusset -- the second-oldest European settlement in what became the…

Wharf Creek Conservation Area

Easy Marshfield Dog friendly Parking

Located in Marshfield, Wharf Creek Conservation Areawith natural wetland habitats. This trail system is perfect for hiking. The trail is nearly entirely in wetlands which can make for a damp…

Wheelwright Park + Barnes Wildlife Sanctuary

Moderate Cohasset Dog friendly Parking

Located in Cohasset, Wheelwright Park + Barnes Wildlife Sanctuary featuring scenic pond views. This trail system accommodates hiking, birding, and skating. When you visit, you'll find a heavily forested area…

Whispering Woods Conservation Area

Moderate Plymouth Dog friendly Parking

Located in Plymouth, Whispering Woods Conservation Area featuring scenic pond views. This trail system is perfect for hiking. The short loop winds through mixed forest with real topographic variety, following…

Whitman Town Park

Whitman Parking

Whitman Town Parkshowcasing historic significance. This trail system is perfect for swimming. The park was added to the National Register of Historic Places in 2004. Try Sydney Ice Pond for…

Whitney & Thayer Woods

Moderate Cohasset Dog friendly Parking

Located in Cohasset, Whitney & Thayer Woods is a 824 acre property showcasing historic significance. The 10 mile trail is perfect for hiking. The trail network consists of approximately 10…

Whitney & Thayer Woods

Whitney Spur Rail Trail

Easy Cohasset Dog friendly

Located in Cohasset, Whitney Spur Rail Trailwith natural wetland habitats. The 1. 5 mile trail is perfect for hiking. Along the way it passes through forest and wetlands with maple,…

Whiton Woods and Cedar Crest

Easy Duxbury Dog friendly Parking

Located in Duxbury, Whiton Woods and Cedar Crest is a 32 acre property featuring scenic pond views. The 1 mile trail is perfect for hiking. At the start of the…

Whortleberry Hollow

Easy Hingham Dog friendly Parking

Located in Hingham, Whortleberry Hollow is a 13 acre property with natural wetland habitats. The 0. 4 mile trail is perfect for hiking. 4-mile trail through the woods and around…

Whortleberry Hollow

Widows Walk Golf Course (seasonal)

Scituate Dog friendly Parking

Located in Scituate, Widows Walk Golf Course (seasonal) is a 100 acre property. This trail system is ideal for hiking and birding. The "pits" as it was known, presented the…

Williams Preserve and Wright Reservoir

Easy Duxbury Dog friendly Parking

Located in Duxbury, Williams Preserve and Wright Reservoir is a 200 acre property featuring scenic pond views. The 3 mile trail is perfect for hiking. Extend your walk into Gifford…

Willow Brook Farm Preserve

Pembroke Parking

Located in Pembroke, Willow Brook Farm Preserve is a 127 acre property with natural wetland habitats. The 3 mile trail is ideal for hiking and birding. The property consists of…

Willow Brook Farm Preserve

Winslow House

Moderate Marshfield Dog friendly Parking

Located in Marshfield, Winslow Housewith natural wetland habitats. This trail system is perfect for hiking. It is a lovely little pocket of Marshfield history to wander, whether or not you…

Wompatuck Pond

Pond Hanson Paddle-friendly

Located in Hanson, Wompatuck Pond featuring scenic pond views. This trail system accommodates hiking, swimming, and skating. This manmade pond forms a scenic backdrop for the town hall, bordered by…

Wompatuck State Park – Doane Street/Cohasset Entrance

Moderate Pond Cohasset Dog friendly Parking Paddle-friendly

Located in Norwell, Wompatuck State Park – Doane Street/Cohasset Entrance is a 500 acre property in this state park system. This trail system offers a pleasant recreational experience. Doane Street…

Wompatuck State Park – Grove Street Entrance (Norwell)

Easy Norwell Dog friendly Parking

Located in Norwell, Wompatuck State Park – Grove Street Entrance (Norwell) is a 500 acre property showcasing historic significance. The 12 mile trail is ideal for hiking and biking. It…

Wompatuck State Park – Leavitt Street Entrance (Hingham)

Easy Pond Hingham Dog friendly Parking Paddle-friendly

Located in Hingham, Wompatuck State Park – Leavitt Street Entrance (Hingham) is a 500+ acre property in this state park system. This trail system is ideal for hiking and biking.…

Wompatuck State Park – Main Entrance (Hingham)

Moderate Pond Hingham Dog friendly Parking Paddle-friendly

Located in Norwell, Wompatuck State Park – Main Entrance (Hingham) is a 500 acre property featuring scenic pond views. The 40 mile trail accommodates hiking, biking, and birding. The land…

Wompatuck State Park – Mt. Blue Street Entrance (Norwell)

Moderate Norwell Dog friendly Parking

Located in Norwell, Wompatuck State Park – Mt. Blue Street Entrance (Norwell) is a 500+ acre property through beautiful woodland. The 40 mile trail is ideal for hiking and biking.…

Woodbine Island Conservation Area

Moderate Marsh Weymouth Dog friendly Parking Paddle-friendly

Located in Weymouth, Woodbine Island Conservation Area featuring scenic pond views. The 0. 16 mile trail accommodates hiking, fishing, and kayaking. 16-mile trail along the edge of Whitman's Pond, plus…

World’s End

Moderate Hingham Dog friendly Parking

Located in Hingham, World’s End is a 244 acre property with natural wetland habitats. This trail system offers a pleasant recreational experience. Overlooking Hingham Bay, it is formed by two…

World’s End

Wyman North Fork Conservation Area

Bridgewater Dog friendly Parking

Located in Bridgewater, Wyman North Fork Conservation Area is a 96 acre property with natural wetland habitats. The 1. 1 mile trail is ideal for hiking and birding. 1-mile blue-blazed…

Browse by town

Abington, Bourne, Braintree, Bridgewater, Brockton, Carver, Cohasset, Duxbury, Halifax, Hanover, Hanson, Hingham, Holbrook, Hull, Kingston, Marshfield, Norwell, Pembroke, Plainville, Plymouth, Plympton, Quincy, Rochester, Rockland, Scituate, Weymouth, Whitman