Top 10 Scenic Rails Trails in Connecticut Every Cyclist Should Ride

Cycling through Connecticut Rails Trails can be likened to pedaling through paradise. Think about the feeling of fresh air on your face, the sound of your bike wheels crunching on the trail, and the breathtaking scenery of nature around you.

Now, let's explore the incredible world of Connecticut Rails Trails. Once upon a time, these trails were train tracks, ferrying people and goods across the state. Now, they're relaxing pathways for cyclists to cross, brimming with calmness and natural beauty. You'll find everything here, from towering forests and gentle streams to charming small towns.

Choosing the top 10 trails from the vast network in Connecticut was no easy feat. We considered several criteria, like the trail's scenic beauty, the level of difficulty for various cyclist capabilities, the richness of the surrounding wildlife, and the trail's historical and cultural significance.

We are about to go on a journey that will introduce you to some of the best Connecticut Rails Trails that every cyclist needs to explore. We're unlocking the gates to nature's hidden gems, waiting to be discovered, admired, and, most importantly, cycled.


I. Air Line State Park Trail

Stepping into the spotlight at number one is the Air Line State Park Trail, a true gem in the crown of Connecticut Rails Trails.

The Air Line State Park Trail is like a window into history, originally built as a railway line in the late 1800s. Today, this trail spans over 50 miles through the heart of eastern Connecticut, offering a unique mixture of natural beauty and historical intrigue.

When selecting our top trails, we had a robust set of criteria in mind. We looked at the variety of scenery, the quality and upkeep of the trail, the diversity of wildlife, and the area's historical significance. The Air Line State Park Trail effortlessly checks all these boxes, setting the bar high for our list.

So, what can you expect when you choose to challenge the Air Line State Park Trail?

1. Diverse Landscapes: From the dense green forests to relaxing marshlands and bubbling streams, the Air Line Trail is a ride of attractive landscapes.

2. Wildlife Encounters: Keep your eyes open, and you might spot an array of wildlife! The Blackledge River Marsh is a hotspot for various animals, from birds to otters.

3. Historic Structures: One cannot forget the iconic Lyman Viaduct. As you cycle across this steel marvel, take a moment to appreciate its panoramic views.

4. Accessibility: The trail is primarily flat, making it perfect for beginners, families, or seasoned cyclists looking for an easy ride.

5. Lengthy Ride: With 50 miles to cover, you'll want to plan your journey. Choose your access points, bring plenty of water and snacks, and prepare to immerse yourself in this enriching cycling adventure.

The Air Line State Park Trail truly offers a cycling experience like no other. It's a harmonious blend of history, nature, and adventure, satisfying every cyclist's soul. It's not just a trail; it's a journey through time and nature that will leave you yearning for more.


II. Bloomfield Greenway Multi-Use Trail

Bloomfield Greenway Multi-Use Trail, with its unique personality, has carved out its own spot in the top 10 CT Rails Trails family.

This trail is a compact yet charming route that spans approximately 2.3 miles, weaving through the town of Bloomfield. While it's considerably shorter than the expansive Air Line State Park Trail, it brings its own charms to the table and offers an experience that leaves a lasting impression.

Our selection criteria remained the same - a blend of scenic allure, trail quality, wildlife encounters, and historical significance. Bloomfield Greenway Multi-Use Trail has managed to tick all these boxes, even within its short stretch.

Go on a journey along the Bloomfield Greenway Multi-Use Trail. Here's what you can expect:

1. A Scenic Stroll: The trail meanders through a mix of residential and commercial areas, providing cyclists with a varied and vibrant backdrop to their ride.

2. Wildlife Sightings: Even within the town, wildlife thrives. Keep an eye out for local bird species that often make their appearance along the trail.

3. Accessible Riding: The trail is relatively flat, making it an excellent choice for beginners, families, or anyone looking for a quick, relaxing ride.

4. A Slice of History: The trail boasts a rich history, having been converted from an old railway line. As you pedal, you're literally riding through the pages of Bloomfield's past.

5. Community Connection: The trail runs close to the heart of the community. You'll find plenty of local businesses to support along the way.

The Bloomfield Greenway Multi-Use Trail may be a short ride, but it's sweet, filled with nature, history, and a touch of local life. Remember, good things often come in small packages!


III. Cheney Rail Trail

Pedaling into the third spot, we have the Cheney Rail Trail. This trail might be a bit of a dark horse among the Connecticut Rails Trails, but it packs quite a punch.

Steeped in history and bursting with natural beauty, the Cheney Rail Trail runs for about 1 mile in the heart of Manchester, Connecticut. The trail is named after the historic Cheney Brothers Silk Manufacturing Company, a nod to the area's rich industrial past.

Like all trails on this list, the Cheney Rail Trail was selected based on our rigorous criteria. It may be short, but it offers an appealing mix of scenic beauty, history, wildlife, and trail quality that's hard to resist.

Go on a journey down the Cheney Rail Trail? Here's what to expect:

1. A Walk Through History: As you traverse the trail, you're stepping into Manchester's industrial past. Take time to appreciate the unique history of this area.

2. Urban Nature: Though it's in the middle of the city, the Cheney Rail Trail offers plenty of natural beauty. The trail is surrounded by greenery and local wildlife, creating a peaceful retreat amid urban life.

3. Easy Riding: With its flat surface and short length, the Cheney Rail Trail is perfect for beginners, families, or anyone looking for a relaxing ride.

4. Connection to Other Trails: The Cheney Rail Trail connects to other nearby trails, offering possibilities for longer, more adventurous rides.

5. A Local Adventure: The trail's urban location means it's easily accessible and offers the chance to explore local Manchester businesses and attractions.

The Cheney Rail Trail is proof that size doesn't always matter. This trail may be brief, but it offers a rewarding and inspiring cycling experience, a blend of history, nature, and urban exploration.

IV. Derby Greenway

Derby Greenway Trail has all the ingredients of an attractive cycling destination, making it a must-visit spot in the Connecticut Rails Trails circuit.

The Derby Greenway, located in the Naugatuck River Valley, boasts a stretch of about 2 miles. It's not just a trail but a celebration of nature, history, and community spirit.

As with our previous selections, the Derby Greenway met our criteria with aplomb. Its scenic beauty is undeniable, the trail's condition is superb, the chance to encounter wildlife is high, and it carries a considerable historical weight that adds to its allure.

So, what can you expect when you decide to cycle the Derby Greenway?

1. Unbeatable Scenery: Running along the Naugatuck and Housatonic Rivers, the Derby Greenway offers awe-inspiring riverfront views. There's something incredibly soothing about cycling together with flowing water.

2. Wildlife Encounters: The rich ecological landscape of the area makes wildlife sightings a common occurrence. Keep your binoculars handy!

3. Smooth Ride: The trail is flat, paved, and well-maintained, making for a pleasant, easy ride. It's perfect for families, casual cyclists, or anyone needing a relaxing spin in the great outdoors.

4. Historical Landmarks: You'll pass several historical landmarks, including the Derby-Shelton Bridge and O'Sullivan's Island area, reminding you of the area's intriguing past.

5. Community Ties: The trail is a favorite among locals and visitors alike, creating a warm sense of community.

The Derby Greenway might be a short ride, but it's an experience packed with scenic beauty, historical landmarks, and booming wildlife. It's a true witness to the idea that great things often come in small packages.



V. Farmington River Trail

Farmington River Trail is a showstopper in the Top 10 CT Rails Trails list.

The Farmington River Trail is a unique, winding path that runs for about 18 miles, circling the Farmington Canal Heritage Trail. It's like a visual symphony, bringing together luxurious greenery, the calm flow of the Farmington River, and vibrant local life in harmony that's music to a cyclist's ears.

As with all our top picks, the Farmington River Trail passed our selection criteria with flying colors. Its rich scenic beauty, excellent trail condition, teeming wildlife, and historical intrigue make it a standout choice.

So, what awaits you on the Farmington River Trail?

1. Scenic Splendor: With the sparkling Farmington River as your cycling companion, the trail offers an ever-changing backdrop of natural beauty. It's a ride that's as calming as it is captivating.

2. Wildlife Sightings: The diverse ecosystem surrounding the trail means you're likely to spot a variety of local fauna. From birds to small mammals, wildlife lovers are in for a treat.

3. A Smooth Journey: The trail's well-kept condition ensures a smooth, enjoyable ride. Despite a few gentle inclines, it's an accessible trail for most cyclists.

4. Historical Touch: The trail's location near the Farmington Canal Heritage Trail adds a layer of historical interest to your ride.

5. Community Experience: The trail weaves through local towns, offering cyclists the chance to engage with the community, support local businesses, and soak up the local atmosphere.

With its blend of natural beauty, intriguing history, and engaging community interaction, the Farmington River Trail is a cycle route that offers much more than just a ride. It's an experience that will linger in your memory long after the journey ends.


VI. Hanover Pond Trail

Hanover Pond Trail, a highlight of the Top 10 CT Rails Trails, has impressed its niche with its unique scenic beauty and local culture mix.

The Hanover Pond Trail runs for nearly 2 miles in Meriden, Connecticut. Nestled in a slice of nature within the city landscape, this trail combines the best of both worlds, creating an unforgettable cycling experience.

As always, our selection criteria were tough. Yet, the Hanover Pond Trail rose to the challenge. It scores highly on all fronts, offering appealing scenery, an excellent trail, ample wildlife, and a taste of local history.

Ready to explore the Hanover Pond Trail? Here's what to expect:

1. Natural Beauty: The trail runs along the shores of Hanover Pond, offering peaceful water views that'll have you reaching for your camera.

2. Wildlife Encounters: Despite its urban setting, the trail is a haven for local wildlife. From waterfowl to small mammals, nature is always on display.

3. Comfortable Cycling: The trail is flat, paved, and well-maintained, ensuring a smooth ride for cyclists of all skill levels.

4. Historical Highlights: The trail winds its way through the area's industrial past, giving you a glimpse into Meriden's rich history.

5. A Local Experience: The trail's urban location means you're never far from local amenities. It's the perfect opportunity to explore Meriden and support local businesses.

The Hanover Pond Trail, with its harmonious blend of nature and city life, offers a cycling experience that's both serene and stimulating. It's a microcosm of Connecticut's diverse landscape, making it a must-ride trail for any cycling enthusiast.


VII. Hop River State Park Trail

Stretching over an impressive 20 miles from Manchester to Willimantic, the Hop River State Park Trail takes cyclists on a journey through various landscapes, from dense forests to historic mill towns.

Like all our top trails, the Hop River State Park Trail excels in our selection criteria. Its combination of rich scenery, great trail quality, abundant wildlife, and historical significance sets it apart.

So, what can you expect when you pedal your way down the Hop River State Park Trail?

1. A Natural Escape: Surrounded by luxurious greenery and crisscrossed by sparkling streams, the trail offers an immersive nature experience. You might forget you're in the heart of Connecticut!

2. Wildlife Wonders: The diverse habitats along the trail provide homes to many wildlife species. Keep your eyes peeled for an unplanned nature show.

3. A Breezy Ride: While the trail's length might seem intimidating, the mostly flat and well-maintained trail ensures a comfortable journey.

4. Historical Intrigue: The trail follows the old Hartford, Providence and Fishkill Railroad corridor. You'll pass several remnants of Connecticut's industrial past, adding an intriguing historical dimension to your ride.

5. Community Connection: As the trail winds through various towns, you'll have plenty of opportunities to experience local life, explore community landmarks, and support local businesses.

The Hop River State Park Trail offers a rich, diverse cycling experience that's hard to match. Its blend of natural splendor, historical interest, and community connections is a testament to the trail's uniqueness. It's a cycling journey that promises to be as inspiring as it is enjoyable.


VIII. Kress Family Trail

Securing its place at number eight is the Kress Family Trail. This lesser-known treasure in the Connecticut Rails Trails collection is really a happiness for cyclists looking for a serene and rewarding ride.

The Kress Family Trail, located in Rocky Hill, stretches for about 1.5 miles. Though short, this trail is packed with charm and is a perfect getaway for cyclists who seek a peaceful retreat within the city's bounds.

As per our selection criteria, the Kress Family Trail makes its mark. Although subtle, its blend of serene beauty, high-quality trail conditions, glimpses of wildlife, and historical significance makes it a standout.

So, what wonders await you on the Kress Family Trail?

1. A Peaceful Retreat: Flanked by trees and offering serene views of the local landscape, the Kress Family Trail is a slice of peace in the heart of Rocky Hill.

2. Surprise Wildlife Sightings: While the trail runs through an urban area, spotting local wildlife along the route is common. A bit of nature's magic in the city!

3. Easy Ride: The trail is well-maintained and relatively flat, making it a breeze for cyclists of all skill levels.

4. Historical Highlights: While the Kress Family Trail doesn't claim a rich industrial history like some other trails on this list, its location in Rocky Hill – a town with a history dating back to 1650 – adds a subtle historical layer to your ride.

5. A Local Affair: The trail is a popular spot for local residents, giving you a chance to experience a slice of community life in Rocky Hill.

The Kress Family Trail may be shorter, but it offers a unique experience steeped in serenity and subtle charm. It's a little piece of paradise that's definitely worth a visit for every cycling enthusiast.


VIIII. Mattabassett Trolley Trail

The Mattabassett Trolley Trail, located in East Berlin, spans a modest 0.7 miles. But don't be fooled by its length - this trail packs a punch of unique charm that makes it stand out.

In line with our selection criteria, the Mattabassett Trolley Trail has its unique set of solid points. Its picturesque views, well-kept trail condition, potential wildlife sightings, and historical relevance make it a compelling contender.

Eager to unravel the secrets of the Mattabassett Trolley Trail? Here's what's in store:

1. Natural Beauty: This short trail presents a picturesque canvas of nature, with the Mattabassett River serving as your peaceful companion throughout your ride.

2. Wildlife Encounters: The riverside location provides an ideal habitat for a variety of creatures. You may catch sight of waterfowl, amphibians, and more.

3. A Smooth Journey: Despite its short distance, the trail is well-maintained and smooth, perfect for a quick and easy ride.

4. Historical Intrigue: The trail gets its name from the old trolley line that once ran along this route, adding an interesting historical flavor to your journey.

5. Local Connection: This trail, popular among locals, is a great way to experience the everyday rhythm of life in East Berlin.

While the Mattabassett Trolley Trail may not be the longest trail on our list, it is a testament to the beauty and charm that can be packed in a short distance. It's a quick escape into nature that's sure to leave you refreshed and inspired.


X. Middlebury Greenway

Rounding out our top 10 Connecticut Rails Trails at number ten is the Middlebury Greenway, an impressive slice of Connecticut's charm that provides cyclists with an unforgettable experience.

The Middlebury Greenway stretches for about 4.5 miles through the heart of Middlebury, offering cyclists an enjoyable and scenic ride that's steeped in local flavor.

As with all our selected trails, the Middlebury Greenway meets our selection criteria with confidence. It boasts lovely scenery, a well-maintained trail, a chance to spot local wildlife, and a smidgen of history, making it a worthy conclusion to our list.

Eager to saddle up and explore the Middlebury Greenway? Here's what you can expect:

1. Scenic Splendor: The trail winds its way through lovely landscapes, offering delightful views of Middlebury's attractive Connecticut atmosphere.

2. Wildlife Sightings: The trail's green surroundings play host to a variety of local fauna. Keep your eyes peeled for those surprise nature moments.

3. A Smooth Ride: The trail is flat and well-paved, ensuring a pleasant ride that's accessible for cyclists of all skill levels.

4. Historical Highlights: Middlebury's rich history subtly seeps into the trail, offering cyclists a taste of the town's past.

5. A Local Experience: As you pedal your way along the trail, you'll pass through key parts of Middlebury, providing an excellent opportunity to immerse yourself in local life.

The Middlebury Greenway is a testament to the beauty and charm of Connecticut's small-town life. It's a journey that's as much about the destination as it is about the ride. So saddle up and experience the magic of Middlebury on two wheels.



Here's a quick roundup of the most commonly asked questions about cycling the rail trails in Connecticut:

1. What are the rail trails in Connecticut?

Rail trails in Connecticut are old railway lines that have been repurposed into recreational trails for biking, walking, and other outdoor activities. They offer a unique way to explore Connecticut's scenic landscapes and rich history.


2. Are the rail trails suitable for all skill levels?

Absolutely! Connecticut's rail trails are typically flat, well-maintained, and span a range of lengths, making them suitable for cyclists of all ages and skill levels. Whether you're a beginner cyclist or a seasoned pro, you'll find a perfect trail.


3. Can I see wildlife on these trails?

Definitely! The trails pass through diverse habitats, providing homes to a wide range of wildlife. From waterfowl on the Hanover Pond Trail to local fauna on the Middlebury Greenway, there's always a chance of spotting wildlife.


4. Are there any historical landmarks along these trails?

Yes! Many of these trails, like the Hop River State Park Trail and the Mattabassett Trolley Trail, follow historic railway corridors and pass through old mill towns, giving you a glimpse into Connecticut's industrial past.


5. Do I need to bring anything specific for these trails?

Standard biking gear should suffice for most of these trails. However, it's always a good idea to pack water, snacks, a first-aid kit, and your camera to capture the stunning views!


6. Can I stop and explore the towns along the trails?


Absolutely! One of the joys of cycling these trails is the opportunity to connect with local communities. So feel free to stop, explore, and support local businesses!

Remember, these trails are shared spaces, so always be mindful of others. Enjoy your cycling adventure on Connecticut's Rail Trails!


7. Are Connecticut's Rails Trails free to access?

Absolutely! All Rails Trails in Connecticut are open to the public and free to access. However, remember to respect the trails and keep them clean for everyone to enjoy.


8. Can I bring my dog along for a ride?

Sure thing, furry friends are welcome on most of the trails. However, they must be leashed at all times and remember to clean up after them. Some trails may have specific rules, so checking beforehand is a good idea.


9. Are the trails suitable for beginners?

Yes, most of Connecticut's Rails Trails offer relatively flat, smooth paths that are perfect for beginners. Trails like the Middlebury Greenway and the Bloomfield Greenway Multi-Use Trail are excellent places to start.


10. What should I bring on my ride?

Always wear a helmet for safety. Also, pack water, snacks, and a basic repair kit in case your bike has a minor breakdown. And don't forget your camera - the scenic views will not be missed!


11. Are the trails open all year round?

Most of the trails are open year-round. However, some may be closed or difficult to navigate during heavy snowfall or other adverse weather conditions. Always check the trail conditions before heading out.


12. Can I cycle the trails at night?

Some trails may close at dusk, while others are open but may not be well-lit. It's advisable to check the specific trail rules and, if night riding is allowed, be sure to use bike lights for safety.


13. Do I need to wear a helmet?


While Connecticut law doesn't require cyclists over the age of 15 to wear a helmet, it's highly recommended for your safety.


Biking on Connecticut's Rails Trails is an experience full of joy, beauty, and adventure. If you have any other questions, don't hesitate to drop them in the comments.

A sneak peek into the top 10 Connecticut Rails Trails you simply must explore. Whether you're a seasoned cyclist or someone just getting started, these trails offer an unforgettable cycling experience.

Don't just take our word for it. Strap on your helmet, gear up and hit the trails. Feel the wind in your hair as you glide down the old railway lines, listen to the symphony of birds as you meander through the forests, and marvel at the historical remnants that remind us of Connecticut's rich past. Take a break, grab a bite in a local cafe, meet the locals, and create your own stories.

Remember, checking the latest trail conditions and local regulations before you set off is always a good idea. Happy pedaling!