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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Activity: State: Reset

#1. Bear Mountain - Mount Riga State Park Trail

Bear Mountain is one of the most popular hiking destinations in the state. A grand stone pyramid crowns its summit, offering unrestricted views which include broad valleys, shimmering lakes, and rugge…

From the guidebook "AMC's Best Day Hikes in Connecticut"
Salisbury , CT - Hiking - 6 miles

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Published by Appalachian Mountain Club Books

#2. Appalachian National Scenic Trail: CT & MA

This 2,155-mile national scenic trail, journeying from Springer Mountain, Georgia to Mount Katahdin, Maine, traverses the northwest corner of Connecticut and western Massachusetts, touring forest, fie…

From the guidebook "Hiking Southern New England"
North Adams , MA - Hiking - 138 miles

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#3. 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

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#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

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#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

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#6. Indian Council Caves Trail

There is magic in a cave. Sometimes spooky magic, but magic just the same. This walk travels to the matrix of boulder hideaways called Indian Council Caves. Yet the caves are only one facet of this lo…

From the guidebook "AMC's Best Day Hikes in Connecticut"
Barkhamsted , CT - Hiking - 4.2 miles

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#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

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#8. Mount Frissell Trail

There is no other place in Connecticut as lofty or as wild as the forests of Mount Frissell. Here the highest elevation in the state hides among dense thickets of mountain laurel, and black bear and b…

From the guidebook "AMC's Best Day Hikes in Connecticut"
Salisbury , CT - Hiking - 4.2 miles

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#9. Castle Craig, Cat-Hole Pass, and East Peak Trail

The Hanging Hills are one of Connecticut’s most easily recognized landmarks. Looming over the city of Meriden, these four traprock ridges and their accompanying rust-colored vertical cliffs seem like…

From the guidebook "AMC's Best Day Hikes in Connecticut"
Meriden , CT - Hiking - 4.6 miles

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#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

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#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

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#12. Cathedral Pines and Mohawk Mountain Trail

Change eventually comes to everything. Such is the case with Cathedral Pines and Mohawk Mountain. These beautiful places of forests and streams lay in the path of a train of tornadoes that swept throu…

From the guidebook "AMC's Best Day Hikes in Connecticut"
Cornwall , CT - Hiking - 3.7 miles

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#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

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#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

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#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

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#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

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#17. Mianus River Gorge Trail

Great gorge and reservoir vistas, old-growth hemlocks, an intricate network of nineteenth-century farmstead walls, glacial erratics, and granite outcroppings highlight one of the better short treks in…

From the guidebook "60 Hikes within 60 Miles: New York City"
Long Ridge , CT - Hiking - 5 miles

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#18. Babcock Circumference Trail

Only ogres and elves are missing from this enchanting hike that threads by bogs, boulders, and fallen trees along several meandering trails. Stone walls and cat briar carpet the undulating forest floo…

From the guidebook "60 Hikes within 60 Miles: New York City"
Greenwich , CT - Hiking - 3.5 miles

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#19. 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

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#20. 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

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