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Cycling routes
United States
Connecticut
Lower Connecticut River Valley Planning Region

Middletown

The best cycling routes around Middletown

5.0

(12)

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Best touring cycling routes Middletown often follow former rail corridors and river valleys, providing varied terrain for cyclists. The landscape features a mix of paved multi-use paths, wooded sections, and some rolling hills. Many routes offer scenic views along waterways and through natural preserves. The region's network of trails caters to different skill levels, from flat, accessible paths to more challenging routes with elevation changes.

Best touring cycling routes around Middletown

  • The most popular touring cycling route is Former Lyman…

Last updated: June 28, 2026

5.0

(1)

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#1.

Former Lyman Viaduct – Air Line Trail loop from East Hampton

62.5km

05:12

400m

400m

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

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Hard

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

Moderate
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Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

5.0

(3)

11

riders

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Popular around Middletown

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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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Rockland Preserve is a 650-acre park with hills, steep rocky cliffs, and woods. The park's centerpiece is Coan Pond.

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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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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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Rockland Preserve is a 650-acre park with hills, steep rocky cliffs, and woods. The park's centerpiece is Coan Pond.

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Rockland Preserve is a 650-acre park with hills, steep rocky cliffs, and woods. The park's centerpiece is Coan Pond.

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Birch Hill Road Open Space West is a nature reserve southeast of Grayville Falls, situated right next to the Air Line State Park Trail. Undeveloped, forested land covers the area between the town's many residential developments, adding to the rural character of this beautiful area.

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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

How many touring cycling routes are available in Middletown?

Middletown offers a diverse selection of touring cycling routes. Across the various Middletown locations, you can find a significant number of routes, with our guide featuring 16 distinct touring cycling routes. These range from easy, paved paths to more challenging trails with elevation changes.

What is the best time of year for touring cycling in Middletown?

While cycling is enjoyable throughout the warmer months, September and October are particularly popular for touring cycling in Middletown, Delaware, offering pleasant weather. Generally, spring and fall provide ideal conditions with milder temperatures and beautiful scenery across all Middletown regions.

Are there easy touring cycling routes suitable for beginners in Middletown?

Yes, Middletown has several easy touring cycling routes perfect for beginners or those seeking a relaxed ride. For instance, the Former Lyman Viaduct loop from East Hampton is an easy option. In Middletown, DE, the Michael N. Castle C&D Canal Trail is largely flat and paved, ideal for a leisurely ride. Lums Pond State Park also offers easy, mostly paved loops.

Are there challenging touring cycling routes for experienced cyclists?

Experienced cyclists looking for a challenge will find options in Middletown. The Former Lyman Viaduct – Air Line Trail loop from East Hampton is a difficult route spanning over 40 miles with significant elevation gain. In Middletown, CT, local bike shops organize road rides with diverse terrain, including challenging hills in areas like Portland Hills.

Can I find long-distance touring cycling routes in Middletown?

Yes, long-distance touring cycling routes are available. The Former Lyman Viaduct – Air Line Trail loop from East Hampton covers over 40 miles. In Middletown, OH, the Great Miami River Valley boasts one of the nation's largest paved trail networks, offering 340 miles of off-road trails for extensive rides.

Are there any circular touring cycling routes in Middletown?

Many touring cycling routes in Middletown are designed as loops, providing a convenient way to start and end in the same location. Examples include the Former Lyman Viaduct loop from East Hampton and the Rockland Preserve – Rockland Preserve loop from Rockland Pump Track. Lums Pond State Park in Middletown, DE, also features cycling loops.

Are touring cycling routes in Middletown dog-friendly?

While specific regulations vary by location and trail, many multi-use paths and rail trails in the Middletown areas generally permit leashed dogs. It's always best to check local park rules or trail signage before heading out with your canine companion to ensure a pleasant experience for everyone.

Where can I find parking for touring cycling routes in Middletown?

Parking is often available at trailheads and state parks. For example, the Saint Georges Trailhead for the Michael N. Castle C&D Canal Trail in Middletown, DE, provides parking, restrooms, and picnic tables. Many other routes, especially those along former rail corridors or in parks, typically have designated parking areas.

What kind of scenery can I expect on touring cycling routes in Middletown?

Touring cycling routes in Middletown offer diverse scenery. You can expect views along waterways like the Chesapeake and Delaware Canal or the Great Miami River, wooded sections, open fields, and rolling hills. Many routes follow former rail corridors, providing a unique perspective on the landscape.

Are there any interesting landmarks or attractions to see along the touring cycling routes?

Yes, there are several interesting landmarks and natural attractions. You might encounter Castle Craig, enjoy a View from West Peak, or pass by Lamentation Mountain. The region also features beautiful lakes such as Bradley Hubbard Reservoir and Crescent Lake Park, offering scenic stops along your ride.

Are there any rail trails for touring cycling in Middletown?

Middletown is well-known for its rail trails. The Michael N. Castle C&D Canal Trail in Middletown, DE, is a prominent example, following a former rail corridor. The Great Miami River Valley in Middletown, OH, also features an extensive network of trails, many of which utilize former railway lines, providing flat and scenic routes.

What do other touring cyclists enjoy the most about touring cycling in Middletown?

The touring cycling routes in Middletown are highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the varied terrain, from flat canal paths to challenging hills, and the scenic beauty of the river valleys and natural preserves. The well-maintained paths and diverse options for all skill levels are frequently highlighted.

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