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Gravel rides
United States
Connecticut
Lower Connecticut River Valley Planning Region

Middletown

The best gravel rides around Middletown

5.0

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Gravel biking around Middletown features a mix of terrain, including hard-packed dirt and gravel roads, particularly within state forests and around reservoirs. The region provides access to extensive natural areas with unmaintained dirt and gravel paths, offering varied landscapes for exploration. These routes often connect to larger trail networks, providing options for different ride lengths and challenges. The area is characterized by its state forests and scenic reservoir crossings.

Best gravel bike trails around Middletown

  • The most popular gravel bike…

Last updated: July 4, 2026

5.0

(1)

10

riders

#1.

Former Lyman Viaduct – Air Line State Park Trail loop from East Hampton

18.6km

01:38

170m

170m

Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

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Tips from the Community

Jamie S.
September 3, 2024, View of the River from Air Line State Park Trail (Southern Section)

The Air Line State Park Trail in Connecticut is a rail trail and linear state park that is a part of the East Coast Greenway. There are several sections including: South (25 miles from East Hampton to Windham), North (21 miles from Windham to Putnam), Thompson addition (6.6 miles from Thompson to the Massachusetts state line), and an additional 3.6-mile spur to Colchester. Recognized as a national recreation trail by the U.S. Department of the Interior in 2002, it offers scenic routes for hiking and biking. This southern section of the trail near East Hampton is a gravel crushed trail that is great to ride on its own, or to access singeltrack in the nearby Salmon River Forest.

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This park runs alongside the Willimantic River, providing scenic views of the water. On the opposite side, there are train tracks where you can occasionally observe interesting carts passing by.

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From here you can take the Colchester Spur Trail. The area surrounding the trail played a small but fascinating role in the American Revolution. Look for markers mentioning skirmish sites and troop movements.

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David Howells
January 22, 2024, Cedar Lake

Beautiful Cedar Lake is a local recreational area for the residents of Chester. Two springs feed into this 80-acre water body. Its tree-lined shore and tranquil setting make it a beautiful vista when cycling past on W. Main Street.

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AverieOutside
January 20, 2024, Air Line Trail

The Air Line Trail is a paved 50-mile multi-use trail that connects the cities of Thompson and Portland. This trail is open to walkers, bikes, and even horses.

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This former railroad trail is now highly popular among hikers, runners, and bikers. Stretching over 20 miles, it passes through several towns. This section features a well-maintained hard packed dirt trail surrounded by lush green forest.

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There is a cute waterfall right next to the road where Pattaconk Brook flows through Town Park. You get a particularly good view if you are travelling south-east to north-west.

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This park runs alongside the Willimantic River, providing scenic views of the water. On the opposite side, there are train tracks where you can occasionally observe interesting carts passing by.

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Frequently Asked Questions

What kind of terrain can I expect on gravel bike trails around Middletown?

Gravel biking around Middletown offers a diverse mix of surfaces. You'll find hard-packed dirt and gravel roads, especially within state forests like Cockaponset and Meshomasic, and around reservoirs. Some routes feature 'mildly hilly, true gravel' sections, while others, like River Road, provide a 'classic hilly one-lane gravel' experience. Expect unmaintained dirt and gravel paths, with some sections potentially having rocks and roots, particularly around the Middletown Reservoir trails in New York.

Are there any family-friendly gravel biking options in Middletown?

Yes, several areas around Middletown are suitable for family-friendly gravel biking. While specific routes vary, the general terrain often includes accessible paths. For example, the Former Lyman Viaduct – Air Line State Park Trail loop from East Hampton is a moderate 12.9-mile path that provides a quicker loop, which might be suitable for families looking for a shorter ride. Additionally, city parks in Middletown, NY, are noted for accommodating various activities including bicycling.

Where can I find scenic viewpoints or natural attractions along the gravel trails?

Middletown's gravel trails offer access to several scenic spots and natural attractions. You can find beautiful views from places like View from West Peak or Higby Cliffs. Reservoir Road in Connecticut is known for being very scenic as it crosses a reservoir. For a unique natural feature, consider visiting Wadsworth Little Falls, a waterfall accessible from some areas.

Are there any long-distance gravel cycling routes in the Middletown area?

For those seeking a longer challenge, the Middletown area offers extensive routes. The Hop River State Trail – Former Lyman Viaduct loop from Town Open Space (Pine Brook) is a significant 56.8-mile trail that leads through varied landscapes and is often completed in about 5 hours 44 minutes. State forests like Cockaponset and Meshomasic also provide extensive networks of dirt and gravel roads that can be linked for longer rides.

What is the best time of year for gravel biking in Middletown?

The best time for gravel biking in Middletown generally aligns with spring, summer, and autumn. These seasons offer pleasant temperatures and drier conditions, making the unmaintained dirt and gravel paths more enjoyable. Autumn, in particular, can be very scenic with fall foliage. Winter conditions can introduce snow and ice, making some trails challenging or impassable, especially in state forests.

Are there any circular gravel bike routes available?

Yes, there are several circular gravel bike routes around Middletown. For example, the Former Lyman Viaduct – Air Line Trail loop from East Hampton is a popular 25.3-mile loop. Another option is the Pattaconk Lake – Pattaconk Brook Waterfall loop from Middlesex County, which is a moderate 33.3-mile circular route.

What do other gravel bikers enjoy most about the trails in Middletown?

The gravel biking routes in Middletown are highly rated by the komoot community, with an average score of 3.7 stars from more than 3 reviews. Reviewers often praise the varied terrain, the scenic beauty of the state forests and reservoir crossings, and the options available for different ability levels, from moderate paths to more challenging, longer routes.

Are there any specific permits or regulations for gravel biking in state forests like Meshomasic?

While general access to state forests like Meshomasic State Forest and Cockaponset State Forest is usually open for recreational activities, it's always a good idea to check for specific regulations or temporary closures, especially concerning motorized vehicles or certain trail uses. For detailed information regarding permits or specific rules, it's best to consult the official Connecticut Department of Energy and Environmental Protection (DEEP) website.

Where can I find parking for gravel bike trails in Middletown?

Parking availability varies by trail and location. Many state forests and trailheads, especially those that are part of larger trail networks, typically have designated parking areas. For routes starting in East Hampton, such as those utilizing the Air Line Trail, you can often find parking near the trail access points. For routes originating from Town Open Space (Pine Brook), look for parking facilities in that vicinity.

Are there any notable landmarks or historical sites I can visit near the gravel trails?

Yes, the Middletown area has some interesting landmarks. For instance, Castle Craig is a prominent man-made monument that offers great views. The region also features unique geological formations like the Glacial Lake Hitchcock Sediment Dam. For more general attractions and things to do in Middletown, Connecticut, you can explore resources like Atlas Obscura's guide.

What are the difficulty levels of gravel bike trails around Middletown?

The gravel bike trails around Middletown cater to a range of difficulty levels. You'll find moderate paths suitable for a relaxed ride, such as the 20.7-mile Former Lyman Viaduct – Air Line State Park Trail loop from East Hampton. For more experienced riders seeking a challenge, there are difficult routes like the 56.8-mile Hop River State Trail – Former Lyman Viaduct loop from Town Open Space (Pine Brook), which features significant elevation changes.

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Browse the best Gravel rides in other regions.

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