Connecticut is bursting with beautiful old rail trails and mountain biking areas just waiting to be explored. Whether you’re headed to the scenic “Quiet Corner” of the state, the bustling city of Hartford, or the western portion of Connecticut, this list of top 10 trails for cycling features the best of the best.

1. Charter Oak Greenway – Hartford, CT

The Charter Oak Greenway is a stunning 16-mile bike path that starts in the state’s capital and makes its way out into the forested suburbs east of the city. The Greenway is a designated segment of the East Coast Greenway, a massive trail that stretches from Maine to Florida, and features several points of interest to enjoy as you cycle. In the downtown area, you’ll pass through the Riverfront Recapture sculpture park along the Connecticut River. It’s a very scenic area featuring beautiful city skyline views, so take the time to enjoy it! The trail continues past the University of Connecticut and through the communities of East Hartford, Manchester, and Bolton, encompassing a wonderful mixture of urban, suburban, and rural scenery. The route ends at Bolton Notch State Park, a beautiful 95-acre state park with rock climbing and hiking trails.

Tips: This trail also connects with Hop River State Park Trail in Bolton, a designated segment of the East Coast Greenway, and passes right by two college campuses and the town of Manchester.

2. Larkin State Park Trail – Middlebury to Southbury, CT

Lankin State Park Trail is a long and narrow state park trail that spans 10.3 miles through a woodsy and refreshing nature area. Despite the prevalence of hills and wetlands in this western portion of the state, this route meanders through the landscape, avoiding those obstacles and providing a flat and easy ride. Those who prefer a tranquil getaway while cycling will enjoy this trail, surrounded by lush deciduous trees, small horse farms, pretty ponds, and small rushing streams. In the autumn, it’s gorgeous and features warm, rich hues of gold, orange, and red that radiate from the trees along the path.

Tips: This route feels very isolated, so you may prefer to ride with a friend if you’re hesitant to go it alone. This trail was also originally designated as a trail for horses, and many still make their way down it. Be ready to encounter them!

3. Farmington Canal Heritage Trail – New Haven to Suffield, CT

If you want to explore all that the state of Connecticut offers by bike, a trip along this route is a great way to do it! The Farmington Canal Heritage Trail is an extensive route that offers about 50 miles of path, stretching nearly the entire length of the state. The trail is split into two sections: a northern and a southern section. It starts in the charming city of New Haven, where you’ll ride through bustling neighborhoods, university campuses, and eventually onto lakes, state parks, and green, open spaces. Once you’re out of the city, the route takes on a more isolated and woodsy feel, but you’re never very far from town. This off-road trail also provides access to points of interest like the Lock 12 Historical Park and an old train depot in Southington before it stops and reappears with the northern section of the route in Southington. This trail segment features an eclectic mix of terrain, including farmland, forests, industrial areas, and quiet neighborhoods, before reaching its end in Suffield.

Tips: Before starting your ride in New Haven, consider taking time to explore the city and Yale University’s campus. Once you complete your cycling adventure, replenish your body’s energy stores with a slice of mouthwatering New Haven-style pizza at one of the local pizzerias. 

4. Middlebury Greenway – Middlebury, CT

The Middlebury Greenway is a short, 4.5-mile trail in New Haven County that’s completely paved. The flat and easy ride is more of a leisurely ride rather than a strenuous workout, but it’s an enjoyable way to explore the town of Middlebury. It follows a former trolley line and runs alongside CT 64, offering a fun and easy adventure through some of Middlebury’s local attractions, including public parks, green spaces, lakes, and bustling business districts. At the western end of the trail, you’ll arrive at the century-old Quassy Amusement Park, featuring fun rides and a water park that kids and adults can enjoy.

Tips: This trail runs along a very busy road, so watch for traffic and stay on the paved trail, especially if you’re cycling with kids.

5. Pomfret Loop – Pomfret, CT

The Pomfret Loop is a serene 13.2-mile bike path in eastern Connecticut, a scenic countryside area known as “The Quiet Corner.” This part of the state offers quiet, natural beauty year-round and is much less congested than other scenic parts of Connecticut. The Pomfret Loop starts in Pomfret, meanders through Woodstock, and then heads back to Pomfret, featuring spectacular views of the tranquil landscape. Along the way, you’ll pass Woodstock’s Roseland Cottage, a historic 1846 summer home-turned-museum featuring rows of stunning, colorful flowers in the summer.

Tips: At the end of the Pomfret Loop, you can also connect to the Thompson Loop, which consists of an additional 10 miles.

6. Hop River State Park Trail – Manchester to Willimantic, CT

Another gorgeous ride through eastern Connecticut, the Hop River State Park Trail features 20 miles of bike trail through a picturesque landscape dotted with shady trees, covered bridges, and sparkling rivers. This rail trail follows the former Hartford, Providence, and Fishkill Railroad beginning in Manchester and continuing past Valley Falls Park and Bolton Notch State Park, both of which are worth a pit stop! Along the route, you’ll also pass small waterfalls, and eventually, you’ll reach a bridge that stretches over the scenic Willimantic River, where the trail ends at Columbia Avenue in Willimantic.

Tips: The Hop River State Park Trail connects to several popular biking routes in the area, including the Charter Oak Greenway, the Rockville Spur (also known as the Vernon Rails-to-Trails), and the Air Line State Park Trail.

7. Moosup Valley State Park Trail – Plainfield to Sterling, CT

The Moosup Valley State Park Trail follows the Moosup River through the eastern Connecticut towns of Plainfield and Sterling. In total, the route offers 5.8 miles of trail that extends to the Rhode Island border. This bike trail features a variety of scenic landscapes, including peaceful meadows, thick forests, and peaceful farmland. It also passes over streams and rivers, so you’re bound to catch a glimpse of the local wildlife as you ride. This route provides plenty of opportunities to explore a few points of interest, including the Sterling Historic District and Quinebaug Valley State Fish Hatchery, which offers trout fishing at certain times of the year.

Tips: Once you reach the Rhode Island border, you can continue your adventure for an additional 7 miles on the Trestle Trail and enjoy even more of the area’s natural beauty.

8. Pequonnock River Trail – Bridgeport to Newtown, CT

The Pequonnock River Trail follows the former Housatonic Railroad and knits together several distinct trails, connecting Bridgeport to Newtown. The route begins in downtown Bridgeport and parallels Housatonic Avenue, with a short segment typically used by Bridgeport residents for commuting purposes. A short gap separates that first stretch of the trail from the more popular trailhead at Crown Street and Glenwood Avenue. Nearby, the Beardsley Zoo and Beardsley Park are two fun and exciting pit stops! From there, the trail continues under CT 8 and crosses over the Pequonnock River, through the 80-acre Twin Brooks Park in Trumbull, Old Mine Park, and William E. Wolfe Park. Many cyclists also use this trail to access the Pequonnock River Wildlife Area in Trumbull and the Centennial Watershed State Forest in Newtown. The route officially ends in the woods on the Newtown town line. 

Tips: Since this trail is broken up into several smaller segments, you’ll have to cross many area roads. Be very careful and watch for traffic, as it may not always stop for cyclists.

9. Case Mountain State Park – Manchester, CT

Head to Case Mountain State Park in Manchester for some of the best mountain biking in the state. This area is well-known for its hilly and challenging landscape, but it rewards bikers with amazing views and excellent technical features. You can combine many of the trails at this state park to create longer loops featuring singletrack and doubletrack routes. Mountain bikers looking for a challenge will enjoy the advanced black trails, offering steep climbs, technical challenges, and thrilling adventures. Be forewarned, though: These trails are very popular, so they can get pretty packed. Anticipate sharing the trails with plenty of other cyclists and hikers.

Tips: Most of the trails here are best for intermediate cyclists, but you can also create your own beginner-friendly loop by stringing some easier trails together.

10. Air Line State Park Trail – East Thompson to East Hampton, CT

The Air Line State Park Trail is a long and beautiful trail in eastern Connecticut, spanning more than 50 miles! The route is perfect for cyclists who want to get out of the city and explore the state’s gorgeous countryside. It’s divided into northern and southern sections: the north half connects East Thompson to the outskirts of Thompson, and the southern half links Pomfret Center (in Pomfret) to East Hampton. Along the route, you’ll find dozens of cute antique shops, thrift stores, local cafes, breweries, restaurants, and the majestic Goodwin State Forest. The Air Line State Park Trail also connects to the Hop River State Park Trail in Willimantic. This bike trail is perfect for cyclists of all abilities, but the gravel, ballast, and crushed-rock surface does make for a bumpy ride in certain areas.

Tips: The nearby Mashamoquet Brook State Park is another worthwhile stop if you’re up for more outdoor adventures near this trail.

Photo Sources:

• Morrowlong, CC BY-SA 4.0, via Wikimedia Commons
• Pi.1415926535, CC BY-SA 4.0, via Wikimedia Commons
• Pi.1415926535, CC BY-SA 3.0, via Wikimedia Commons
• Pi.1415926535, CC BY-SA 4.0, via Wikimedia Commons
• Pedro Xing, CC0, via Wikimedia Commons
• Pi.1415926535, CC BY-SA 4.0, via Wikimedia Commons

Sources:

1. https://www.ctvisit.com/listings/charter-oak-greenway
2. https://www.ctvisit.com/listings/larkin-state-park-trail
3. https://fchtrail.org/
4. https://www.middlebury-ct.org/parks-recreation/pages/middlebury-greenway
5. https://www.traillink.com/trail/middlebury-greenway/
6. https://www.ctvisit.com/getaways/biking-quiet-corner
7. https://www.traillink.com/trail/hop-river-state-park-trail/ 
8. https://portal.ct.gov/DEEP/State-Parks/Parks/Moosup-Valley-State-Park-Trail
9. https://www.traillink.com/trail/pequonnock-river-trail/ 
10. https://www.nemba.org/trails/connecticut/case-mountain-state-park-manchester
11. https://portal.ct.gov/DEEP/State-Parks/Parks/Air-Line-State-Park-Trail
12. https://www.traillink.com/trail/air-line-state-park-trail/