Best Trails of Connecticut

This list represents the most popular trails in Connecticut (learn more about Top Trails). Use this list to plan your next Connecticut outdoor trip. Select a state and/or activity below to find even more top trails.

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#1. Bear Mountain


From the parking area, pale-blue-blazed Undermountain Trail immediately passes a kiosk on the right with a posted map; trail maps are sometimes available here. The trail heads west and begins a gentle…
From the guidebook "AMC's Best Day Hikes in Connecticut"
Mount Frissell, CT - Hiking - 6 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#2. Appalachian Trail: Kent to St. Johns Ledges


As a day hike this is a gem, with a superb reward at the end in the form of a tremendous tumble of boulders down a precipitous but manageable cliff. Thrills and chills without having to scale the Mat…
From the guidebook "Exploring the Appalachian Trail: Hikes in Southern New England"
Kent, CT - Hiking - 4.9 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Stackpole Books

#3. Selden Neck Campground


From the guidebook "Best Tent Camping: New England"
Haddam, CT - Campgrounds Best Trail in CT - Click to view allBestCampgrounds Trail - Click to view all (About Top Trails)
Published by Menasha Ridge Press

#4. Farmington Canal Linear State Park Trail


The Farmington Canal Trail is a popular destination for people of all ages. The trail has a wide paved surface, mileage and kilometer markers, benches, solid wood bridges, and signs at road crossings…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Cheshire, CT - Rail-Trails - 8 miles    Best Trail in CT - Click to view allBestRail-Trails Trail - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#5. Devil's Den Preserve


In Weston and Redding. A broad-swinging loop travels several of the named trails, touring much of the preserve; side spurs visit granite ledges and a boulder ravine. Special attractions: Rich hardwoo…
From the guidebook "Hiking Southern New England"
Redding, CT - Hiking - 7.2 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Falcon Publishing

#6. The Weir Preserve


Enter the preserve, owned by the Weir Farm Art Center—a private, nonprofit organization that supports Weir Farm National Historic Site—on a wide former woods road blazed yellow and flanked by stone wa…
From the guidebook "AMC's Best Day Hikes in Connecticut"
Cannondale, CT - Hiking - 1.1 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#7. Metacomet Trail, Talcott Mountain


Three miles west of Bloomfield. This segment of the long-distance Metacomet Trail tours the rolling ridge of Talcott Mountain, topping rock outcrops and visiting Heublein Tower for vistas. Special at…
From the guidebook "Hiking Southern New England"
Bloomfield, CT - Hiking - 19.5 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Falcon Publishing

#8. Mount Frissell


From the parking area on East Street (called Mount Washington Road in Connecticut), near the Connecticut–Massachusetts state line, red-blazed Mount Frissell Trail heads northwest on an old woods road,…
From the guidebook "AMC's Best Day Hikes in Connecticut"
Mount Frissell, CT - Hiking - 5.2 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#9. Sessions Woods Wildlife Management Area


A gazebo at the far end of the lot contains property information. Beaver Pond trailhead, however, is located at the end of the wide graveled roadway immediately north (right) of the parking area. Foll…
From the guidebook "AMC's Best Day Hikes in Connecticut"
Bristol, CT - Hiking - 3 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#10. Appalachian Trail: Bull's Bridge to Kent


"Schaghticoke" (ska-ti-coke) means "the place where the river divides" in Mohegan, a Native American language. You are climbing Schaghticoke Mountain and soon will pass through a reservation by the s…
From the guidebook "Exploring the Appalachian Trail: Hikes in Southern New England"
Kent, CT - Hiking - 7.6 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Stackpole Books

#11. The Mianus Maze


This unique trail system, located in the Mianus River Park near Greenwich, Connecticut, is a maze of singletrack and hard-packed old carriage roads, a tantalizing network of mountain bike trails suita…
From the guidebook "Mountain Biking Eastern New York"
Greenwich, CT - Mountain Biking - 14 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Falcon Publishing

#12. Wolcott Trail and Burr Pond


From the parking lot, follow the light-blue-blazed Wolcott Trail—named for the Civilian Conservation Corps’ Camp Wolcott—north (counterclockwise) around the pond. Ducks often loaf on nearby boulders t…
From the guidebook "AMC's Best Day Hikes in Connecticut"
Winsted, CT - Hiking - 2.75 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#13. Stony Creek to Thimble Islands


The Thimble Islands are a picturesque spot on the Connecticut coast. It’s as though the pink-granite-ringed islands of the Maine coast migrated south just off the quiet town of Stony Creek. On the mar…
From the guidebook "Sea Kayaking Along the New England Coast"
Stony Creek, CT - Sea Kayaking - 9.5 miles    Best Trail in CT - Click to view allBestSea Kayaking Trail - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#14. Ragged Mountain Preserve Trail


Located in Berlin, CT. Within this 563-acre open space acquired through the Land and Water Conservation Fund, a demanding loop journeys through restful mixed woods and traverses a stirring cliff rim.…
From the guidebook "Hiking Southern New England"
Berlin, CT - Hiking - 6.1 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Falcon Publishing

#15. Bear Hill Loop


This loop walk is on the Eastern division of the Mattabesett Trail, between Route 154 and the Connecticut River. It’s a scenic stretch with a high spot, nicknamed the Summit, and a big ledge called th…
From the guidebook "Short Nature Walks: Connecticut"
Middletown, CT - Hiking - 4.2 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Falcon Publishing

#16. Appalachian Trail: Falls Village to Salisbury


There is so much to see and do on this hike that while the mileage (9.9 overall) suggests that a day hike is feasible, we recommend making it an overnight trip. The setting for the shelter and campsi…
From the guidebook "Exploring the Appalachian Trail: Hikes in Southern New England"
Falls Village, CT - Hiking - 9.9 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by Stackpole Books

#17. Bantam Lake


Bantam Lake, the largest natural lake in Connecticut, encircled by a country road and replete with an uncrowded sandy beach, the 4,000 acres of forest in the state's largest nature center and wildlife…
From the guidebook "Short Bike Rides in Connecticut"
Litchfield, CT - Road Biking - 10 miles    Best Trail in CT - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#18. Airline State Park Trail (South)


Panoramic views of the surrounding Connecticut hills and valleys characterize the Airline State Park Trail. Its most dramatic features are its two hidden viaducts, which offer expansive views of the s…
From the guidebook "Rails To Trails: Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire, Maine"
Willimantic, CT - Rail-Trails - 5 miles    Best Trail in CT - Click to view allBestRail-Trails Trail - Click to view all (About Top Trails)
Published by The Globe Pequot Press

#19. Bantam River, Bantam Lake, and Little Pond


The Bantam River represents one of the preeminent paddling resources in western Connecticut. Flowing through a 4,000-acre nature preserve protected by the White Memorial Foundation, it’s a great place…
From the guidebook "Quiet Water Massachusetts, Connecticut, and Rhode Island: AMC's Canoe and Kayak Guide, 3rd Edition"
Litchfield, CT - Flatwater Paddling & Canoeing Best Trail in CT - Click to view allBestFlatwater Paddling & Canoeing Trail - Click to view all (About Top Trails)
Published by Appalachian Mountain Club Books

#20. Westport Ramble


Whether you're seeking an invigorating ride into the countryside or a leisurely ramble along the coast, this ride will satisfy. It begins near a large park on Long Island Sound, Sherwood Island State…
From the guidebook "Best Bike Rides in New England"
Westport, CT - Road Biking - 25.3 miles   
Published by The Globe Pequot Press