A bird sitting on a nest of eggs.

Hiking Near Holland, 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.

Dean Pond Loop

Hike Route

Dean Pond Loop

Fishing
easy
0.65 mi
+25 ft
Mountain Road Trail

Hike Route

Mountain Road Trail

Historical
easy
2.66 mi
+278 ft
North-South Trails Loop

Hike Route

North-South Trails Loop

Scenic
easy
3.05 mi
+388 ft
Peaked Mountain Trail

Hike Route

Peaked Mountain Trail

Birding
easy
1.95 mi
+486 ft
Lunden Pond and Temple Brook Loop

Hike Route

Lunden Pond and Temple Brook Loop

Birding
easy
2.26 mi
+183 ft
Laughing Brook Wildlife Sanctuary Loop

Hike Route

Laughing Brook Wildlife Sanctuary Loop

Birding
easy
3.21 mi
+319 ft
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Adventurous Routes

These routes go beyond 10 miles and are built for days when you want to cover more ground and push a little deeper. Expect longer distances, more effort, and bigger payoffs — whether that’s remote terrain, summit views, or a full-day challenge. Ideal for hikers looking to go farther and stay out longer.

Shenipsit Trail

Hike Route

Shenipsit Trail

River/Creek
strenuous
50.18 mi
+5,334 ft
Robert Frost Trail

Hike Route

Robert Frost Trail

Birding
strenuous
43.37 mi
+7,005 ft
Ware River Rail Trail

Hike Route

Ware River Rail Trail

Historical
moderate
12.87 mi
+297 ft
Shenipsit Trail: Case Mountain to Gay City

Hike Route

Shenipsit Trail: Case Mountain to Gay City

Birding
moderate
12.7 mi
+1,842 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.

Leadmine Mountain Conservation Area Loop

Hike Route

Leadmine Mountain Conservation Area Loop

Birding
easy
5.12 mi
+433 ft
Buffumville Lake Loop

Hike Route

Buffumville Lake Loop

Birding
easy
6.55 mi
+220 ft
West Thompson Lake

Hike Route

West Thompson Lake

Birding
moderate
7.19 mi
+244 ft
Wallis Pond Loop Trail

Hike Route

Wallis Pond Loop Trail

Birding
easy
5.49 mi
+266 ft