A bird sitting on a nest of eggs.

Hiking Near Canaan, 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.

Bartholomew's Cobble Trail

Hike Route

Bartholomew's Cobble Trail

River/Creek
easy
3.55 mi
+511 ft
Lime Kiln Farm Wildlife Sanctuary Loop

Hike Route

Lime Kiln Farm Wildlife Sanctuary Loop

Birding
easy
2.13 mi
+177 ft
Lion's Head

Hike Route

Lion's Head

Views
easy
1.09 mi
+544 ft
Leffingwell Loop

Hike Route

Leffingwell Loop

Birding
easy
2.32 mi
+383 ft
CT State Highpoint/Tri-point Out and Back

Hike Route

CT State Highpoint/Tri-point Out and Back

Geologically Significant
strenuous
3.06 mi
+1,176 ft
Guilder Pond Loop

Hike Route

Guilder Pond Loop

Fall Colors
easy
0.79 mi
+83 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.

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
Kite Hill-Fox HIll and Charcoal Loop

Hike Route

Kite Hill-Fox HIll and Charcoal Loop

moderate
5.24 mi
+584 ft
Halfway Brook-Hubbard River Trails

Hike Route

Halfway Brook-Hubbard River Trails

Historical
easy
5.08 mi
+508 ft
Macedonia Ridge Trail

Hike Route

Macedonia Ridge Trail

Views
strenuous
6.39 mi
+1,788 ft