6 Best Bike Rides in Connecticut for Outdoor Lovers

*Links in this article may be affiliate links, from which we may earn commission. See our Privacy Policy for full details.

Connecticut’s natural and historic charm is on display all year long, and bike paths that wind through the state offer visitors a chance to experience the Nutmeg State’s beauty up close. With its beach communities, picturesque town centers, small and vibrant cities, and stunning open spaces, Connecticut has an abundance of delight to share with visitors, all in a small package.

While traversing a small state is easy enough by car, why not get closer to the charm by taking one of the best bike rides in Connecticut? Pick a ride or two and take advantage of the bountiful opportunities to explore southern New England!

Table of Contents

Farmington Canal Heritage Trail (southern section)

New Haven, Hamden, Cheshire, Southington

Reaching from New Haven to Suffield, the Farmington Canal Heritage Trail spans fifty-six miles that run nearly the entire length of the state in two sections. This route, which is split into a northern section and a southern section, is a great choice for anyone wishing to tour the breadth of Connecticut’s offerings.

Starting at the southern end in New Haven, enjoy the city before you start your ride by walking along Long Wharf, taking a stroll through the campus of Yale University, or savoring famous New Haven-style pizza at Frank Pepe’s, Sally’s Apizza, or Modern Apizza.

The trailhead for the Farmington Canal Heritage Trail is located inconspicuously on Temple Street in New Haven, and you’ll shortly be whisked away from the hustle and bustle through neighborhoods and university campuses, then past lakes, state parks, and open spaces. Even though you’ll traverse through woods and feel far away, you’ll never stray too far from town.

This bike ride offers the best of both worlds: peaceful riding on paved paths where you’re safely off the road, with access to restaurants, amenities, and accommodations near the trail. As you head north, stop at the Lock 12 Historic Park in Cheshire and the train depot in Southington to learn about the history of the canal and the former railroad tracks where the bike path now runs.

From Southington to Plainville, the formal trail takes a break, but adventurous riders can take the roads to pick up the northern section of the trail in Southington. Farms, forests, neighborhoods, and some industrial areas characterize the northern part of the Farmington Canal Heritage Trail.

Air Line State Park Trail

Portland, East Hampton, Colchester, Hebron, Columbia, Lebanon, Windham, Chaplin, Hampton, Pomfret, Putnam, Thompson

Head to the Air Line State Park Trail and soak in the solitude and tranquility this path offers. If you’re seeking inspiration and the city isn’t quite doing it for you, take a ride, walk, or run on this eastern Connecticut path to feel the comfort and freedom of nature. At over 50 miles long, the Air Line trail has plenty of options for rides long and short, and for adventure seekers of all varieties.

A gap in the town of Pomfret means the trail isn’t off-road end to end, but there are still countless ways to have a great time on the path. If you like antiquing, ride through East Hampton, Columbia, and Hebron; in these towns, you’ll find antique shops and thrift shops galore, like Trailside Treasures, Lighthouse Antiques, and Kindoro Thrift Store. Make sure you only select small treasures, or you may need to come back with a car to retrieve them!

If a ride with cafes, breweries, and interesting restaurants is more your speed, ride the Air Line Trail through the Willimantic section of Windham, stopping at Willimantic Brewing Company, Grounded Coffee Company, or Stone Row Kitchen and Bar. Nature lovers can’t go wrong riding along any section of the trail, but the stretch from North Windham to Pomfret Center is particularly majestic because you’ll trek through Goodwin State Forest, past Hampton Reservoir, and close to Mashamoquet Brook State Park. In short, this long trail has something for riders of every variety!

Charter Oak Greenway

Hartford, East Hartford, Manchester, Bolton

Starting in the capital city of Hartford, the Charter Oak Greenway connects riders to the eastern suburbs and a variety of trailside sights and amenities. Over the course of sixteen paved miles in Hartford, East Hartford, Manchester, and Bolton, riders will traverse through urban, suburban, and more rural areas, highlighting this small state’s versatility.

Starting at Riverfront Park in Hartford, riders will almost immediately cross the scenic Connecticut River. Be sure to stop and take in the skyline views behind you as you traverse the Founders Bridge. Once you’re back on land, you’ll pass through East Hartford’s Great River Park, by the University of Connecticut’s Rentschler Field, then parallel major roadways from the safety of an off-road path.

As you get close to Manchester, the greenway does take riders along the road for short stretches before returning to an off-road path. Also in Manchester, you’ll pass by Manchester Community College, historic neighborhoods, and Charter Oak Park. If you need a break, turn off at Main Street in Manchester for a break at a restaurant or cafe or to explore some of the shops and parks in this walkable downtown.

As you make your way east, you’ll enter more wooded surroundings as you approach Bolton. The trail ends at Bolton Notch, where riders have the chance to continue their ride by hopping on the Hop River State Park Trail. There are many opportunities to extend your ride by taking either a spur trail or continuing your ride at either end of the Charter Oak Greenway.

Middlebury Greenway

Middlebury

Looking for a bike ride in New Haven County? Looking for an amusement park in the area too? You’re in luck because the Middlebury Greenway is an off-road bike path that takes riders to Quassy Amusement Park at its western end. The amusement park may be at the very end of the ride, but the journey getting there has plenty of fun along the way too.

Over the course of 4.5 miles, riders will pass by public parks, natural spaces, lakes, and business districts. Be sure to stop and read some of the historic interpretive signage to learn about the area in days gone by. Once you arrive at the western end of the greenway, take a break at old-school Quassy Amusement Park for a ride on its famous wooden roller coaster, carousel, or water slides. Or, let your childish side come out to play in the arcade.

Too hungry to enjoy the amusements? Ride back east, following the same path, and you’ll pass by restaurants of all varieties. Try out Pies & Pub for pizza, Maggie McFlys for family-friendly local craft eatery fare (and a Connecticut staple), or stop by the Middlebury Station plaza for quick grab-and-go options. The Middlebury Greenway is completely paved, making it a simple and satisfying trek for riders of all skill levels and all ages.

Sue Grossman Still River Greenway

Winchester and Torrington

In bucolic Litchfield County, the Sue Grossman Still River Greenway brings riders on a sojourn along a river, by wildflowers, and through wetlands. This family-friendly trail is just about three miles long, fully paved, and flat, with only a few road crossings. Parking areas at both ends of the trail make this an easy out-and-back ride in either direction.

Visit during the summer and you’ll be treated to a calming green escape, or visit during the fall and the flora around you will shroud your ride in magnificent autumnal colors. If your bike ride has you craving more time in nature, there are plenty of options in the surrounding area to enjoy the serenity of the woods and wildlife for even longer.

Nearby, you’ll find Paugnut State Forest and Burr Pond State Park, which feature miles of hiking trails, plenty of opportunities for wildlife sightings, a chance to go fishing, and endless opportunities to find inner stillness. Two miles north of the Winchester trailhead, the town center of Winsted has a walkable Main Street with restaurants and cafes that will satisfy any craving.

Moosup Valley State Park Trail

Plainfield and Sterling

Following along the Moosup River, the Moosup Valley State Park Trail takes bicycle riders along six miles of varied path in Connecticut all the way to the Rhode Island border, where an additional seven miles of off-road pathway continue on. As you ride through scenic farmland, lively meadows, and lush forests, and over streams and rivers, you will be experiencing a rich diversity of ecosystems and a host of soothing landscapes.

Formerly a railroad, this trail is full of history. Be sure to stop at the trestle bridge, the Cranska Thread Mill and the Sterling Historic District. No ride is complete without a top at the Quinebaug Valley State Fish Hatchery either. Depending upon the time of year, you may get a chance to see young trout or even go fishing at the hatchery.

Because only the most western end of the trail is paved, this ride is best in the summer and fall months, when the dirt will be packed down. The Moosup Valley State Park Trail is great for visitors who want to take their time, and who want to get off their bike and explore the area up close.

You might also like:

Mallory Sullivan

Mallory grew up in Connecticut, and after some time living in Ireland, Montana, and Virginia, she felt called back home to New England. She lives in Boston and writes about the intersection of urban living, outdoor adventure, and enjoying the simple things at SimpliCity Outside. Her favorite New England adventures involve hiking, finding ice cream shops, and exploring small towns.