A bird sitting on a nest of eggs.

Hiking Near Killingworth, 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.

Chatfield Trail

Hike Route

Chatfield Trail

easy
2.54 mi
+413 ft
Orange Vista Trail

Hike Route

Orange Vista Trail

Views
easy
1.73 mi
+345 ft
Castle Craig

Hike Route

Castle Craig

Fall Colors
moderate
2.99 mi
+577 ft
Lake Wintergreen Loop

Hike Route

Lake Wintergreen Loop

Fishing
moderate
1.59 mi
+56 ft
Maples Farm Outer Loop

Hike Route

Maples Farm Outer Loop

Dogs Allowed
easy
1.24 mi
+182 ft
Crescent Lake Loop

Hike Route

Crescent Lake Loop

Fall Colors
moderate
2.21 mi
+311 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.

Northwoods Loop

Hike Route

Northwoods Loop

Geologically Significant
strenuous
10.32 mi
+1,724 ft
Shenipsit Trail

Hike Route

Shenipsit Trail

River/Creek
strenuous
50.18 mi
+5,334 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.

West Rock Ridge Loop

Hike Route

West Rock Ridge Loop

Cave
strenuous
7.69 mi
+956 ft
Ragged Mountain Blue and Red Blazed Loop

Hike Route

Ragged Mountain Blue and Red Blazed Loop

Fall Colors
strenuous
5.59 mi
+1,040 ft
Mashomack Preserve Loop

Hike Route

Mashomack Preserve Loop

Birding
easy
8.48 mi
+363 ft