Hikes near Winchendon, Massachusetts

20 hikes · 8 trailheads nearby

465 sunset spots near Winchendon →

Hikes

Monadnock Recreational Rail Trail

7.7 mi · ▲ 84 ft

2.1 mi · ▲ 55 ft

2.4 mi · ▲ 55 ft

Bottle Tree Lane Extension

4.8 mi · ▲ 285 ft

Bottle Tree Lane Extension & Jeep Road from 140 parking lot via Calvin Coolidge

7 mi · ▲ 338 ft

6.3 mi · ▲ 147 ft

3.9 mi · ▲ 175 ft

McLaughlin Trail

1.9 mi · ▲ 0 ft

North Camping Area Beach & McLaughlin Trail

2 mi · ▲ 0 ft

North Ashburnham Road

2.9 mi · ▲ 190 ft

Lake Dennison–Otter River, 5 beaches

7.8 mi · ▲ 111 ft

Main Street via Boston and Maine Railroad Alignment (1874-1940)

5.8 mi · ▲ 81 ft

2.1 mi · ▲ 308 ft

Old County Road

6.9 mi · ▲ 278 ft

Otter River via Boston and Maine Railroad Alignment (1874-1940)

5.9 mi · ▲ 27 ft

Birch Hill Reservoir Area Beach & Lake Dennison Picnic & Swim Area via Boston and Maine Railroad Alignment (1874-1940)

2.8 mi · ▲ 27 ft

Lost Lake & Old County Road

6.1 mi · ▲ 309 ft

Show 3 less-wild hikesHide 3 less-wild hikes

Hunts Pond & Ware River Rail Trail

11.5 mi · ▲ 138 ft

Whitney Pond & North Central Pathway

4.4 mi · ▲ 27 ft

Lake Monomonac & Kinglet's Clipper

1.9 mi · ▲ 246 ft

Nearby Trailheads

North Central Pathway