A bird sitting on a nest of eggs.

Hiking Near Winsted, Connecticut

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.

Ordway-Searles-Sattler Loop

Hike Route

Ordway-Searles-Sattler Loop

Historical
easy
3.65 mi
+289 ft
Healthy Heart Loop

Hike Route

Healthy Heart Loop

easy
1.41 mi
+55 ft
Richardson Brook Wildlife Sanctuary Loop

Hike Route

Richardson Brook Wildlife Sanctuary Loop

Geologically Significant
easy
1.51 mi
+291 ft
York Lake Loop Trail

Hike Route

York Lake Loop Trail

Birding
easy
2.27 mi
+64 ft
Leffingwell Loop

Hike Route

Leffingwell Loop

Birding
easy
2.32 mi
+383 ft
Bartholomew's Cobble Trail

Hike Route

Bartholomew's Cobble Trail

River/Creek
easy
3.55 mi
+511 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.

Halfway Brook-Hubbard River Trails

Hike Route

Halfway Brook-Hubbard River Trails

Historical
easy
5.08 mi
+508 ft
Heublein Tower from Reservoir 6

Hike Route

Heublein Tower from Reservoir 6

Views
moderate
6.29 mi
+608 ft
Rand's View Out and Back

Hike Route

Rand's View Out and Back

Fall Colors
strenuous
5.25 mi
+1,323 ft
Bear Mountain

Hike Route

Bear Mountain

Birding
moderate
5.23 mi
+1,555 ft
Macedonia Ridge Trail

Hike Route

Macedonia Ridge Trail

Views
strenuous
6.39 mi
+1,788 ft
Ragged Mountain Blue and Red Blazed Loop

Hike Route

Ragged Mountain Blue and Red Blazed Loop

Fall Colors
strenuous
5.59 mi
+916 ft