5.0
(1)
20
riders
4
rides
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.
Last updated: July 4, 2026
5.0
(1)
10
riders
18.6km
01:38
170m
170m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
riders
86.4km
05:47
810m
810m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5
riders
92.8km
06:13
610m
610m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
33.4km
02:06
410m
410m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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