A bird sitting on a nest of eggs.

Hiking Near Wineglass, Montana

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.

Pine Creek Falls

Hike Route

Pine Creek Falls

Birding
moderate
2.43 mi
+446 ft
Frog Rock

Hike Route

Frog Rock

Views
easy
2.23 mi
+877 ft
Chestnut Mountain

Hike Route

Chestnut Mountain

Views
strenuous
0 mi
+0 ft
Bear Canyon Trail

Hike Route

Bear Canyon Trail

Dogs Allowed
moderate
4.55 mi
+673 ft
Drinking Horse Mountain

Hike Route

Drinking Horse Mountain

River/Creek
moderate
2.38 mi
+674 ft
Bozeman's M Trail

Hike Route

Bozeman's M Trail

Views
easy
1.43 mi
+894 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.

Montana Trail Section 15

Hike Route

Montana Trail Section 15

moderate
68.5 mi
+13,048 ft
Montana Trail Section 16

Hike Route

Montana Trail Section 16

Views
moderate
94.63 mi
+10,931 ft
North Fork Deep Creek Trail CE

Hike Route

North Fork Deep Creek Trail CE

moderate
11.18 mi
+4,529 ft
West Pine Creek

Hike Route

West Pine Creek

Birding
strenuous
11.86 mi
+2,616 ft
North Dry Creek

Hike Route

North Dry Creek

Less Crowded
strenuous
13.7 mi
+3,143 ft
West Fork Boulder River

Hike Route

West Fork Boulder River

Cave
moderate
12.61 mi
+3,127 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.

Livingston Peak

Hike Route

Livingston Peak

Views
strenuous
7.2 mi
+3,198 ft
Pine Creek Lake

Hike Route

Pine Creek Lake

Birding
strenuous
9.45 mi
+3,890 ft
Chestnut Mountain

Hike Route

Chestnut Mountain

Views
strenuous
5.25 mi
+2,571 ft
Mt. Ellis

Hike Route

Mt. Ellis

Views
strenuous
5.21 mi
+3,384 ft
Sourdough Canyon (Bozeman Creek Trail)

Hike Route

Sourdough Canyon (Bozeman Creek Trail)

Birding
easy
9.43 mi
+813 ft
Grassy Mountain

Hike Route

Grassy Mountain

Views
moderate
8.96 mi
+2,036 ft