A bird sitting on a nest of eggs.

Hiking Near Pinehurst, Massachusetts

Shorter Routes icon

Shorter Routes

These hikes keep it under 5 miles and climb less than 1,500 feet, making them ideal for quicker outings or lower-key days. Perfect for a morning stretch, a casual afternoon, or getting outside without committing to a big push. Don’t let the stats fool you — many still pack in great views and rewarding moments.

Estabrook Woods Loop

Hike Route

Estabrook Woods Loop

Lake
easy
3.5 mi
+133 ft
Whipple Hill Loop

Hike Route

Whipple Hill Loop

Birding
moderate
2.23 mi
+253 ft
Brackett Pond Loop

Hike Route

Brackett Pond Loop

Fall Colors
easy
3.54 mi
+246 ft
Walden Pond

Hike Route

Walden Pond

Birding
easy
1.75 mi
+54 ft
Beaver Brook Loop

Hike Route

Beaver Brook Loop

Fall Colors
moderate
2.69 mi
+271 ft
Virginia Woods Loop

Hike Route

Virginia Woods Loop

Birding
moderate
0.85 mi
+131 ft

Other Nearby Routes

Not finding what you're looking for? These additional nearby hikes offer more ways to get outside and explore the area. With a mix of lengths, difficulty levels, and terrain, you're likely to find something that fits your plans for the day. And remember, you can always use the onX Route Builder to create your own adventure from scratch.

Two Rod Road and Davis Corridor

Hike Route

Two Rod Road and Davis Corridor

Lake
easy
6.48 mi
+271 ft
Skyline Trail

Hike Route

Skyline Trail

Birding
moderate
7.33 mi
+1,176 ft
Lynn Woods Loop

Hike Route

Lynn Woods Loop

Birding
moderate
6.65 mi
+633 ft
Assabet River National Wildlife Refuge + Rail Trail

Hike Route

Assabet River National Wildlife Refuge + Rail Trail

Less Crowded
moderate
9.28 mi
+112 ft
Cutler Park Blue Heron Trail

Hike Route

Cutler Park Blue Heron Trail

Birding
unknown
6.99 mi
+80 ft
Eight Mile Tour

Hike Route

Eight Mile Tour

strenuous
7.12 mi
+954 ft