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Routes
Road cycling routes
United States
Vermont
Windsor County

Springfield

The best road cycling routes around Springfield

52

riders

10

rides

Road cycling routes around Springfield traverse a landscape characterized by river valleys, rolling hills, and rural roads. The region features a mix of open countryside and areas with historical landmarks like covered bridges. Elevations are generally moderate, providing varied terrain for road cyclists.

Best road cycling routes around Springfield

  • The most popular road cycling route is Roadbike loop from Perkinsville, a 29.3 miles (47.2 km) trail that takes 2 hours 7 minutes to complete, offering a moderate challenge through…

Last updated: May 21, 2026

14

riders

#1.

Roadbike loop from Perkinsville

47.2km

02:07

450m

450m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Moderate

8

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

4

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Tips from the Community

Jamie S.
February 15, 2024, Toonerville Trail along Black River

Toonerville Trail is a short, paved, multi-use trail that traverses along the Black River on an old railroad bed. This is a great place to keep an eye out for animals like kingfishers, ducks, and beavers as you ride along this trail.

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The Cornish-Windsor Bridge was built in 1866 and is the longest wooden covered bridge in the country. It's an iconic way to cross the Connecticut River and travel between New Hampshire and Vermont. Despite being nearly 160 years old, it still carries traffic every day. There is a pull-out here, where you can stop and take photos.

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It is worth taking the Old Connecticut River Road to pass through the riverside rural idyll. There are great views of the river all along its length, and a sense of space and calm.

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The Cornish-Windsor Bridge was built in 1866 and is the longest wooden covered bridge in the country. It's an iconic way to cross the Connecticut River and travel between New Hampshire and Vermont. Despite being nearly 160 years old, it still carries traffic every day. There is a pull-out here, where you can stop and take photos.

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Frequently Asked Questions

What is the general difficulty level of road cycling routes around Springfield?

The road cycling routes in the Springfield area are primarily rated as moderate. There are no routes specifically categorized as easy or difficult in our current selection, making them suitable for cyclists with some experience looking for a balanced challenge.

How many road cycling routes are available in the Springfield region?

There are over 10 road cycling routes documented on komoot for the Springfield area, offering a variety of options for exploring the region's landscapes.

What are the typical distances and durations for road cycling routes near Springfield?

Road cycling routes around Springfield vary in length, generally ranging from approximately 13 to 48 miles (21 to 77 km). Most routes can be completed in about 1 hour 30 minutes to 3 hours 30 minutes, depending on the specific route and your cycling pace.

Are there any beginner-friendly road bike paths in Springfield?

While all listed routes are rated as moderate, their varied distances and elevations mean some might feel more accessible. For instance, the Roadbike loop from Davidson Hill is one of the shorter options at about 13 miles (20.8 km), which could be a good starting point for those building endurance.

What kind of scenery can I expect on road cycling routes in Springfield?

The routes in Springfield traverse diverse scenery, including picturesque river valleys, gently rolling hills, and quiet rural roads. You'll experience a mix of open countryside and areas featuring historical landmarks.

Are there any challenging road cycling routes for experienced riders?

While all routes are rated moderate, the longer options provide a greater endurance challenge. The Cornish-Windsor Covered Bridge – Old Connecticut River Road loop from Cheshire Bridge, at nearly 48 miles (77 km) with significant elevation gain, offers a more demanding ride for those seeking a longer day in the saddle.

What is the best time of year for road biking in Springfield?

The best time for road biking in Springfield is typically from spring through fall. During these seasons, the weather is generally mild, and the natural scenery of river valleys and rolling hills is at its most vibrant. Winter cycling may be possible but often depends on snow and ice conditions.

Are there any circular road bike routes available?

Yes, many of the road cycling routes around Springfield are designed as loops, allowing you to start and end at the same point. Examples include the popular Roadbike loop from Perkinsville and the Roadbike loop from Chester.

What historical landmarks or points of interest can I see along the road cycling routes?

Many routes in the Springfield area pass by historical landmarks. Notably, the Cornish-Windsor Covered Bridge – Old Connecticut River Road loop from Cheshire Bridge takes you past the iconic Cornish-Windsor Covered Bridge, a significant historical structure.

Where can I find parking for road bike trailheads in Springfield?

Specific parking information varies by route. However, many routes start from towns or public areas where parking is generally available. It's advisable to check the individual route details on komoot for suggested starting points and potential parking options near the trailhead.

What do other road cyclists enjoy most about road cycling in Springfield?

Road cyclists using komoot often praise the varied terrain, which includes river valleys and rolling hills, and the opportunity to explore rural roads and historical landmarks like covered bridges. The moderate difficulty of the routes is also frequently appreciated, offering a good balance for many riders.

Are there any less crowded road cycling routes in the Springfield area?

While specific crowd levels can vary, many of the routes traverse rural roads, which tend to be less trafficked than urban areas. Exploring routes slightly off the main popular paths, such as the Old Connecticut River Road loop from Black River, might offer a more tranquil experience.

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