The Longest Biking Trail in Connecticut

Written by Kathryn Dueck
Updated: July 26, 2023
Share on:


If you’re an autumn lover, the state of Connecticut might be high on your list of places to visit. Renowned for its beautiful fall foliage, it provides a great cycling experience. However, its attractions aren’t limited to just one season. Year-round, it boasts excellent trails for nature lovers hoping to immerse themselves in America’s natural wonders. The longest biking trail in Connecticut allows cyclists to take in the scenery over the course of several days, catering to both experienced and inexperienced cyclists. Read on to find out where it is and what it’s called!

What is the Longest Biking Trail in Connecticut?

Air Line State Park Trail

The longest biking trail in Connecticut is the Air Line State Park Trail, winding 49.6 miles through a variety of scenic terrain.

©Morrow Long / CC BY-SA 2.0 – License

The longest biking trail in Connecticut is the Air Line State Park Trail. It runs for 49.6 miles from East Thompson to East Hampton, winding through the counties of Middlesex, New London, Tolland, and Windham. The southern end of the trail lies in East Hampton at Main Street between Summit Street and Walnut Avenue. The northern trail end lies in East Thompson at the Connecticut-Massachusetts state line near E. Thompson Road (0.7 miles east of New Road).

The trail came into being as a railway line in the late 1860s running from New York to Boston. Once a popular train route for wealthy passengers, it fell into decline at the turn of the century when technological advancements made train cars too heavy for the line. It continued as a transport route for freight and local passengers until 1955, when flooding destroyed bridge construction in Putnam. It never recovered from this blow. Later, however, it would go on to become one of Connecticut’s best-loved trails. Today, construction continues to make the trail even longer and better.

The Air Line State Park Trail

Cycling, Bicycle, Mountain Bike, Mountain Biking


The Air Line State Park Trail gained its name from its shape. The trail itself is a level line through Connecticut, representing a straight line “drawn in the air” from New York to Boston. Its surface composition varies from ballast and crushed stone to dirt and gravel.

The trail currently divides into 3 sections: the south section from East Hampton to Windham, the north section from Windham to Pomfret, and the Thompson addition.

South Section: East Hampton to Windham

The south section of the Air Line State Park Trail runs for 22 miles. This part of the trail is in better condition than any other, with incredible opportunities to view nature and wildlife along the way. In addition to this, several towns provide places to rest and refuel before continuing on the journey. For cyclists hoping to make their trip a multi-day excursion, there are accommodation options along the route.

This part of the route features two massive viaducts built up from the original railway construction. It also winds through state forests and wildlife management areas. Town parks and other local destinations add a touristy touch to the experience.

North Section: Windham to Putnam

The north section of the Air Line State Park Trail runs for 21 miles. This part of the trail varies from complete to under development. Areas under development may be more or less difficult to navigate by road bikes, making mountain bikes more feasible. The trail ends in Putnam and resumes nearby in southern Thompson.

Thompson Addition

The Thompson addition, currently under construction, runs for 6.6 miles. The trail ends in East Thompson after picking up in southern Thompson near the border of Putnam. The original rail ballast is still in place along parts of this section. This section continues the Air Line State Park Trail to the Massachusetts border, where cyclists have the option to continue on into the state or turn back. As parts of this section remain uncompleted, cyclists should expect possible delays and diversions.

Navigating the Route

mountain bike on sunny day in forest

Cyclists may choose to complete the trail over several days.


The Air Line State Park Trail is fairly easy with a level grade. Due to ongoing construction, some sections may be difficult to navigate with just a road bike, making a mountain bike the better choice overall. Though much of the route is rural, it passes through several communities, including East Hampton, Windham, and Putnam. Cyclists may choose to complete the trail over several days for a more leisurely experience.

Practicing courtesy when cycling on the Air Line State Park Trail is important. Other forms of traffic utilize the trail, from hikers to joggers to equestrians. Generally, cyclists must give way to both foot traffic and horseback riders. Horses spook easily and may bolt if frightened, so it’s vital to give them plenty of warning and space to pass. In the winter, cross-country skiers also use the route.

Where is the Air Line State Park Trail Located on a Map?

Starting from East Hampton, Connecticut, the trail winds its way through diverse landscapes, including charming towns, dense forests, and tranquil wetlands. As visitors traverse this scenic path, they are treated to breathtaking views of rolling hillsides and sparkling rivers.

For those seeking directions to access the Air Line State Park Trail, there are multiple entry points along its route. One popular starting point is located at Main Street in East Hampton. From here, hikers can embark on their journey by following clearly marked signs that guide them through the enchanting wilderness.

Another convenient entrance can be found at Hebron Avenue in Glastonbury. This location provides ample parking facilities for visitors who wish to explore sections of the trail further northward or southward.

Wildlife on the Air Line State Park Trail

A Timber Rattlesnake striking prey



are common in Connecticut.

©Joe McDonald/

Connecticut is a state thriving with animals, and the Air Line State Park Trail allows cyclists the opportunity to see many of them in their natural habitats. Forests, coasts, and wetlands all nurture a variety of life across this small state.

The state animal, perhaps surprisingly, is the sperm whale. Though trail users may not have the chance to see it on their way through, this massive marine mammal has played a vital role in Connecticut’s history. Whalers in the state hunted it more than any other species, contributing to its sharp decline over the years. Today, sperm whales are an endangered species, numbering only about 300,000 individuals worldwide. Before the whaling era, this number may have been as high as 1.1 million.

Connecticut has a number of predators roaming its various habitats. Cyclists would do well to watch out for the likes of black bears, coyotes, bobcats, weasels, badgers, and red foxes. Grey seals, harbor seals, and porpoises hunt in the state’s coastal waters.

Likewise, Connecticut has its share of reptiles in the form of snakes, turtles, and salamanders. The timber rattlesnake and the copperhead are both venomous but not widespread; most other snakes in this state are harmless. Turtle sightings may include the common snapping turtle and the painted turtle. Many different species of lizards and salamanders roam the state including the mole salamander and the marbled salamander.

The Connecticut state bird is the American robin, though other avian species may be visible in the skies. Bald eagles and barn owls are both endangered species in the state while blue jays, northern cardinals, and thrushes are more common.

If you’re an avid cyclist with plans to travel to the Constitution State, don’t miss out on the longest biking trail in Connecticut, the Air Line State Park Trail.

The photo featured at the top of this post is © Morrow Long / CC BY-SA 2.0 – License / Original

Share on:
About the Author

Kathryn Dueck is a writer at A-Z Animals where her primary focus is on wildlife, dogs, and geography. Kathryn holds a Bachelor’s Degree in Biblical and Theological Studies, which she earned in 2023. In addition to volunteering at an animal shelter, Kathryn has worked for several months as a trainee dog groomer. A resident of Manitoba, Canada, Kathryn loves playing with her dog, writing fiction, and hiking.

Thank you for reading! Have some feedback for us? Contact the AZ Animals editorial team.