Hiking Trails in CT

This page is a compilation of some interesting hiking trails in Connecticut.  Some are common, some  are hidden gems, something for everyone from the beginner hiker to the expert trail master.  

Black Hog Brewery Hiking Trail - Bridle Trail, Oxford CT

Plan an excursion to the Black Hog Brewing Company in Oxford CT for a tasting.  This side trail from the Bridle Trail will lead you directly to the brewery!  Numerous starting points on the Bridle trail offer short or long hikes to the brewery.

Difficulty: Easy

Leatherman's Cave- Mattatuck Trail, Watertown CT

A 4 mile loop trail highlighting Leatherman's Cave

Difficulty: Moderate

Elderslie Preserve Hiking Trails - Woodbridge CT

 Home of the glacial erratics, 5 mile out and back hike.

Difficulty: Easy (the orange trail is moderate)

Naugatuck Forest Trail - Whittemore Trail - Beacon Cap Trail - Bethany Veteran's Memorial Park, CT

A 4 mile loop hike

 Difficulty: Moderate

Osbornedale State Park - Derby CT - A Hiking Excursion on the Red Trail from the Kellogg Center

Just over 3 miles, an intriguing hike in the heart of an unexpected place, Derby, CT!

Difficulty: Moderate

Paugussett Trail - Shelton CT - Buddington Rd to Indian Well State Park

 A 9 mile out and back hike.  

Difficulty: Moderate (due to it's length)

 Zoar Trail, Newtown, CT

A 7 mile loop hike with scenic views of Prydden Falls

Difficulty: Moderate to Challenging

Shelton Lakes Recreation Path - Shelton CT

Difficulty: Easy Terrain/Moderate Length

An out and back 8.5 mile hike on wide crushed gravel path (or can be a 2 car 4.2 mile hike) 

 Sticks and Stones Farm, Newtown CT, A Unique Hiking and Camping Experience

 A truly unique property with numerous hiking trails and enchanted cabins

Rockhouse Hill Sanctuary, Oxford CT

Difficulty: Easy-Moderate

Timberlands Preserve - Guilford CT

Over 15 miles of trails, make your own loop trail

Difficulty: Easy to Moderate

For more hiking in CT trails and info see our Hiking in CT Board on Pinterest

See all of our Hiking-Camping Gear