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Top Spots

Wenakeening Woods and Idylbrook Loop

Holliston, Massachusetts

4.11 mi / 381 ft gain

Wenakeening Woods Loop

Holliston, Massachusetts

1.62 mi / 177 ft gain

Idylbrook Conservation Land Loop

Medway, Massachusetts

1.65 mi / 190 ft gain

New, Top Down and Long Run Trail Loop

Holliston, Massachusetts

4.79 mi / 397 ft gain

New, Holliston, Bypass, Main, Three Sisters and Deer Trail

Holliston, Massachusetts

6.9 mi / 607 ft gain

Sherborn Red Trail

Sherborn, Massachusetts

4.1 mi / 374 ft gain

New Trail and Holliston Highway Loop

Holliston, Massachusetts

1.43 mi / 89 ft gain

Hike the Ashland Reservoir Trail

Ashland, Massachusetts

5.0
3.2 mi / 68 ft gain

Swamp Bypass, Kitchen, Rock Garden, Teetering Rock Trail

Holliston, Massachusetts

2.33 mi / 197 ft gain

Places to stay

West Hill Park

Northbridge, Massachusetts

West Hill Park

Buffumville Lake (Group Shelters)

Charlton, Massachusetts

Buffumville Lake (Group Shelters)

West Thompson Lake Campground

Thompson, Connecticut

West Thompson Lake Campground

Boston / Cape Cod KOA Holiday

Middleborough, Massachusetts

Boston / Cape Cod KOA Holiday

Westville Recreation Area

Sturbridge, Massachusetts

Westville Recreation Area

Normanton Farms

Litchfield, New Hampshire

Normanton Farms

From $100 / 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