Connecticut’s landscape is crisscrossed by a network of historic rail corridors transformed into scenic multi-use paths. Whether you are looking for a long-distance cycling challenge or a quiet woodland stroll, these eight trails represent some of the state’s finest “rails-to-trails” conversions. I have spent time on nearly all of these with my ebike and they are a great way to explore the state.
1. Farmington Canal Heritage Trail
The Farmington Canal Heritage Trail is the “granddaddy” of Connecticut rail trails, stretching roughly 54 miles through the state from New Haven to the Massachusetts border. Primarily paved with asphalt, this trail offers a smooth, continuous ride through diverse landscapes—from the urban energy of Yale University to the tranquil suburban stretches of Cheshire and the scenic farms of Simsbury. It follows the path of a 19th-century canal and subsequent railroad, passing historic locks and restored depots along the way. You can also do the loop west along the Farmington River that connects up with the main trail in Simsbury
More Info: https://fchtrail.org/
2. Air Line State Park Trail
Divided into two distinct segments, the Air Line Trail spans approximately 50 miles across eastern Connecticut. Named for the “straight as an arrow” rail line that once connected New York and Boston, the trail features a crushed stone and gravel surface. The southern section (East Hampton to Windham) is famous for its dramatic viaducts—the Rapallo and Lyman—which offer breathtaking views of the forest canopy from high above the valley floor.
More Info: https://ctparks.com/parks/air-line-state-park-trail
3. Housatonic Rail Trail (Monroe)
Located in Monroe and often referred to as the Monroe Rail Trail, this 5-mile gem is part of the larger Pequonnock River Valley Greenway. The trail features a well-maintained crushed stone surface that is exceptionally flat, making it ideal for families and casual walkers. It winds through the lush woods of Wolfe Park and parallels the scenic Pequonnock River, offering a cool, shaded canopy even in the height of summer. If you actually start south at Bearsdley Park in Bridgeport you can wind thru Trumbull into Monroe before it ends near the Newton border for a total of 16 miles.
More Info: https://www.traillink.com/trail/pequonnock-river-trail/
4. Hop River State Park Trail
The Hop River State Park Trail is a 20.2-mile corridor of crushed stone and packed dirt that cuts through the heart of eastern Connecticut’s “Quiet Corner.” Connecting Manchester to Willimantic, the trail is known for its rugged, natural beauty. You’ll pass through deep rock cuts, over wooden bridges, and under a unique covered bridge in Andover. Because it feels more remote than many other trails, it’s a favorite for those looking to escape into the deep woods.
More info: https://ctparks.com/parks/hop-river-state-park-trail
5. Moosup Valley State Park Trail
Tucked away in Plainfield and Sterling, the Moosup Valley State Park Trail runs for 5.8 miles to the Rhode Island border. This trail is more rustic than others on this list, with a surface consisting of dirt, gravel, and some original railway ballast. It provides a peaceful, backcountry experience as it hugs the banks of the Moosup River, eventually connecting to Rhode Island’s Trestle Trail for those looking to cross state lines.
More Info: https://ctparks.com/parks/moosup-valley-state-park-trail
6. Shelton Lakes Recreation Path
Not a traditional rail trail but its commonly known as the “Rec Path,” this 4.5-mile trail in Shelton is a masterpiece of local conservation. The surface is a fine crushed stone that is handicap accessible and exceptionally well-graded. The path links several city reservoirs—Silent Waters, Pine Lake, and Hope Lake—offering constant water views and numerous opportunities for birdwatching and photography within a heavily wooded greenway.
More info: http://www.sheltonconservation.org/recreation/shelton_trails.html
7. Norwalk River Valley Trail (NRVT)
The Norwalk River Valley Trail is an ambitious project that currently features several completed sections, with the most popular being the Wilton Loop (approx. 5 miles) and the Norwalk harbor section. The trail utilizes a mix of crushed stone, asphalt, and boardwalks. The Wilton section is particularly scenic, featuring wide stone-dust paths that meander through the woods and along the river, providing a vital green link in a bustling part of Fairfield County. Eventually they want to expand it along Rte 7 to Danbury.
More info: https://www.nrvt-trail.com/ourtrail
8. New Milford River Trail
The New Milford River Trail currently offers about 5 miles of scenic pathway along the Housatonic River. The trail is a hybrid experience: the Sega Meadows section features a crushed stone path through a riverside park, while the River Road section utilizes a hard-packed dirt and gravel road that is closed to most through-traffic. It offers stunning, unobstructed views of the river and is a popular spot for both cyclists and anglers.
More info: https://nmbikewalk.org/