Skip to content
America’s Trails

Top 10 Trails in Connecticut

By: Gene Bisbee
May 17, 2021

Connecticut's Charter Oak Greenway | Photo by TrailLink user ctaci
Connecticut's Charter Oak Greenway | Photo by TrailLink user ctaci

Railroads and canals both played huge roles in Connecticut’s early economic development. Today those corridors serve as trails for bicyclists, walkers, equestrians and others seeking quality time outdoors. Many are heavily wooded, creating shade on hot summer days and colorful displays in the fall. They also provide alternative transportation opportunities for commuters in the Constitution State’s largest cities. Long-distance travelers will find 98 trail miles of the 3,000-mile-long East Coast Greenway within the state’s borders, as well as segments of the New England Rail-Trail Network.

Air Line State Park Trail 

Connecticut's Air Line State Park Trail | Photo by Liz Sewell
Connecticut’s Air Line State Park Trail | Photo by Liz Sewell

Counties: Middlesex, New London, Tolland, Windham

Many Connecticut residents make a bee-line to the Air Line State Park Trail when taking flight to the outdoors. Named for a historical Boston to New York City railroad, the trail rolls for 55 miles—with a few gaps—from the northeast border with Massachusetts to the heart of the state near Middleton. The gravel, ballast and crushed-rock surface can make for a rough ride in places, but the forested surroundings—especially when splashed with color in the fall—create a pleasant passage. It connects to the Hop River State Park Trail about midway in the village of Willimantic, where history buffs will enjoy the Connecticut Eastern Railroad Museum. The trail serves as a link in the six-state New England Rail-Trail Spine Network and the 3,000-mile East Coast Greenway running between Maine and Florida. 

Hop River State Park Trail

Connecticut's Hop River State Park Trail | Photo by Bill Cannon
Connecticut’s Hop River State Park Trail | Photo by Bill Cannon

Counties: Hartford, Tolland

Travelers encounter three tunnels and a covered bridge as they navigate the 20-mile Hop River State Park Trail in eastern Connecticut. The crushed-stone surface mostly rambles through remote woodlands interspersed by deep, seepy railroad cuts that provide cool shelter in the summer and spectacular ice displays in the winter. Meandering along the Hop River and its tributaries between Manchester and Willimantic, the trail provides another segment of the East Coast Greenway. Many villages along the route date to Colonial times. The trail meets the 4.2-mile Vernon Rails-to-Trails (Rockville Spur) in Vernon and the 55-mile Air Line State Park Trail in Willimantic.

In Windham, the Hop River Trail meets the Air Line Trail on this bridge over the Willimantic River. | Courtesy Connecticut DOT-DEEP

Related: Connecticut’s Hop River State Park Trail

Read Blog

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)

Connecticut's Vernon Rails-to-Trails | Photo by Yvonne Mwangi
Connecticut’s Vernon Rails-to-Trails | Photo by Yvonne Mwangi

County: Tolland

What better way to explore the historical surroundings of Rockville in northern Connecticut than from the Vernon Rails-to-Trails’ Rockville Spur? The 4.2-mile crushed-stone trail peels off the Hop River State Park Trail in Vernon and heads toward the one-time booming textile manufacturing center of Rockville. The trail crosses the scenic Tankerhoosen River on a footbridge and continues through a wooded corridor to the National Register of Historic Places district in Rockville, featuring architecture reminiscent of the 1800s. Visitors can learn about the local textile and railroad history at the Vernon Rails-to-Trails trailhead in Vernon.

Farmington Canal Heritage Trail 

Connecticut's Farmington Canal Heritage Trail | Photo by TrailLink user nmfuko
Connecticut’s Farmington Canal Heritage Trail | Photo by TrailLink user nmfuko

Counties: Hartford, New Haven 

The evolution from canal to railroad to trail tells the history of the Farmington Canal Heritage Trail. The 48-mile trail begins on the urban campus of Yale University in New Haven, but takes on a more rural flavor as it heads north to the Massachusetts state line. The corridor follows a short-lived canal completed in 1835 that was replaced in 1847 by a railroad that ran until the 1980s (a small segment is still active in Plainville). The longest paved trail in the state, its asphalt surface and proximity to population centers makes it one of the most popular. The trail joins the Farmington River Trail in two places. The East Coast Greenway shares the trail from Simsbury to New Haven, minus the gap between Plainville and Southington. The New England Rail-Trail Spine Network incorporates the entire trail length.

Capital Crescent Trail clean-up | Photo courtesy RTC Capital Crescent Trail clean-up | Photo courtesy RTC

Sign up for eNews if you’d like to receive our monthly newsletter, featuring news, events, stories, special offers and ways to get involved.

Sign up for eNews

Farmington River Trail

Connecticut's Farmington River Trail | Photo by Liz Sewell
Connecticut’s Farmington River Trail | Photo by Liz Sewell

County: Hartford

The Farmington River Trail runs a C-shaped circuit through the forests and communities west of Hartford. It connects at both ends with the Farmington Canal Heritage Trail to create a frequently used 26-mile loop. The trail itself is listed at 16 miles, although some of that is on low-traffic roads between Canton and Simsbury, where you’ll also find less than a mile on dirt/crushed stone. The rest of the trail is paved. The scenic Farmington River flows along the southern half of the trail and is home to several historical factories and the Canton Historical Museum in Collinsville, a good half-way stop for refreshments or shopping. 

Pequonnock River Trail

Connecticut's Pequonnock River Trail | Photo by Eli Griffen
Connecticut’s Pequonnock River Trail | Photo by Eli Griffen

County: Fairfield

The historical seaport of Bridgeport on Long Island Sound anchors 14 miles of trail that runs north to the Colonial-era town of Newtown. The Pequonnock River Trail stitches together these locally developed trails that follow the former Housatonic Railroad. Riverside parkland is a big draw for trail users. They use the trail, some of which is paved, to visit such destinations as the Beardsley Park and Zoo in Bridgeport, the 5-mile-long Pequonnock River Wildlife Area in Trumbull, and the Centennial Watershed State Forest in Newtown. The segment in downtown Bridgeport is separate from the northern sections of trail.

Charter Oak Greenway 

Connecticut's Charter Oak Greenway | Photo by TrailLink user lughnerson
Connecticut’s Charter Oak Greenway | Photo by TrailLink user lughnerson

County: Hartford

Named for a park located midway on the Hop River, the Charter Oak Greenway heads some 16 paved miles from the State Capitol in downtown Hartford to woodsy suburbs east of the city. The trail passes through downtown green spaces as it enters the Riverfront Recapture sculpture park that spans the Connecticut River. A mile-long gap marks the jump to East Hartford, where the trail continues as a side path to interstate highways until it junctions with Hop River State Park Trail in Bolton. The trail skirts two college campuses and the Colonial-era town of Manchester along the route. It also has been designated as a segment of the East Coast Greenway. 

Larkin State Park Trail

Connecticut's Larkin State Park Trail | Photo by John M. Joy
Connecticut’s Larkin State Park Trail | Photo by John M. Joy

County: New Haven

The woodsy environs of the Larkin State Park Trail make this an ideal destination to escape the sun under a leafy canopy in the summer or enjoy up-close leaf peeping in the fall. At one time a link on the New York & New England Railroad, the 11-mile trail rolls between Southbury and Naugatuck just southwest of Waterbury. Founded as the Larkin State Bridle Trail geared toward equestrians, the pathway is widely enjoyed by people on horseback. Fat-tired bicycles are recommended for those on wheels, as the trail surface of crushed stone, gravel, cinder and dirt can get rough and soggy, especially after wet weather.

Middlebury Greenway

Connecticut's Middlebury Greenway | Photo by Bill Cannon
Connecticut’s Middlebury Greenway | Photo by Bill Cannon

County: New Haven

Many people take the Middlebury Greenway just for amusement. The 4.5-mile paved trail that crosses the town of Middlebury touches on parks, historic districts, business centers and a century-old amusement park that still provides thrilling rides and a water park. The trail follows a former trolley line between Waterbury and Woodbury that delivered revelers to the Lake Quassapaug Amusement Park, later shortened to the Quassy Amusement Park. Today the trail runs alongside CT 64 and passes numerous entrances in the business district.

Windsor Locks Canal State Park Trail

Connecticut's Windsor Locks Canal Trail | Photo by Jim Brown
Connecticut’s Windsor Locks Canal Trail | Photo by Jim Brown

County: Hartford

Fishermen can be a common sight on the 5.4-mile Windsor Locks Canal State Park Trail in the northwest corner of the state. It’s not surprising, as the trail occupies a narrow sliver of land between the Connecticut River and the historical Enfield Falls Canal. The asphalt trail itself replaces the towpath used by mules to tow barges along the canal in the mid-1800s, avoiding the river’s rapids. The wooded isle draws wildlife, including bald eagles. The state closes the trail from November through the spring so the bald eagles can nest in peace.

Special acknowledgments: Tom Sexton, Director of RTC’s Northeast Region

Rail-Trails: Southern New England Guidebook

Want to experience one of these or some of the other great trail destinations in Connecticut, Massachusetts and Rhode Island? You’ll find maps, helpful details and beautiful photos of 52 multiuse trails across the region in our Rail-Trails: Southern New England Guidebook.

When you subscribe to Rails to Trails magazine, you’ll have access to many other features like this one. Our magazine is a premium of Rails to Trails membership. Join today to start receiving the magazine!

Find your next trail on TrailLink

or Browse Trails Near You
Gene Bisbee
Gene Bisbee

Gene Bisbee is a freelance writer who covers bicycle touring issues on his blog at He’s also author of the book “Falcon Guide: Best Bike Rides Seattle.”

Donate today!


Everyone deserves access to safe ways to walk, bike, and be active outdoors.