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

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

Northbridge, Massachusetts

West Hill Park

Charlton, Massachusetts

Buffumville Lake (Group Shelters)

Thompson, Connecticut

West Thompson Lake Campground

Middleborough, Massachusetts

Boston / Cape Cod KOA Holiday

Sturbridge, Massachusetts

Westville Recreation Area

Litchfield, New Hampshire

Normanton Farms

From $100 / night

Guides and stories

5 Tips for Finding Beautiful Fall Foliage in Massachusetts

Gustavo Quiros

Quick links