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Routes
Road cycling routes
United States
Vermont
Windham County

Jacksonville

The best road cycling routes around Jacksonville

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Road cycling routes around Jacksonville are characterized by the city's extensive park system and coastal landscapes. The region features flat terrain, with dedicated paved trails and scenic road routes through wetlands, woodlands, and along the Atlantic coast. While generally low in elevation, some routes offer varied scenery through natural preserves and along waterways.

Best road cycling routes around Jacksonville

  • The most popular road cycling route is View of the Deerfield River – Hoosac Tunnel East Portal loop from Whitingham,…

Last updated: April 30, 2026

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riders

#1.

View of the Deerfield River – Hoosac Tunnel East Portal loop from Whitingham

50.8km

02:28

700m

700m

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

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Moderate

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard
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Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard

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

Moderate

4

riders

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

Moderate

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Popular around Jacksonville

Hiking around Jacksonville

Tips from the Community

Tyler Sanders
February 27, 2024, Pelham Lake Beach

Named after Fort Pelham from the French and Indian War, the lake provides a pleasant view as you ride, along with a beach area for cooling off if you decide to take a break. Additionally, there are miles of trails surrounding the lake to explore if you choose to combine your ride with some hiking.

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This 40 acre woodland was donated to the Franklin Land Trust by Alastair Maitland in 1992. This cool stretch of road takes you along the forest offering shaded roads in the summer time and amazing foliage colors in the fall. The forest is popular with bird-watchers, so keep your eyes peeled as you ride through here, you never know what you might see.

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Historic covered bridges such as this one are traditional in the area, and it is great to see them maintained. The Bissel Covered Bridge was built in 1881. By the mid-20th century the bridge was due to be replaced by a modern steel and concrete structure. The local town opposed the new structure, and the original bridge was rebuilt and kept to the original specifications. The bridge still features a wooden structure and wooden floor.

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Mill Brook Reservoir is a small lake surrounded by trees. If you pull off the main road by the old covered bridge there is a viewing platform where you can see the waterfall from Mill Brook as it fills the reservoir.

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The Hoosac Tunnel is a working 4.75-mile (7.64 km) active freight railroad tunnel in western Massachusetts. The East Portal of the tunnel can be found in the town of Florida. It is on the big bend of the Deerfield River and not far from the roadside, so it is easy to go and visit.

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The Hoosac Tunnel is a working 4.75-mile (7.64 km) active freight railroad tunnel in western Massachusetts. The East Portal of the tunnel can be found in the town of Florida. It is on the big bend of the Deerfield River and not far from the roadside, so it is easy to go and visit.

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Lisa
October 12, 2023, Molly Stark statue

This statue honors Elizabeth Page "Molly" Stark, the wife of General John Stark, who won the Battle of Bennington during the American Revolutionary War. Molly herself is said to have been a staunch, fierce, and devoted woman during the difficult times of war.

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Here you can have a wonderful view of the Deerfield River. This 122-kilometer-long river has its source in the Green Mountains, south of Vermont. It is the right tributary of the Connecticut River, which flows through the US states of Vermont and Massachusetts.

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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes in Jacksonville?

Jacksonville's road cycling routes are generally characterized by flat terrain, making them accessible for various skill levels. You'll find dedicated paved trails and scenic road routes that wind through coastal landscapes, wetlands, and woodlands. While elevation changes are minimal, the diverse natural preserves and waterways offer varied scenery.

How many road cycling routes are available in the Jacksonville area?

There are over 7 road cycling routes available in the Jacksonville area, catering to different preferences and skill levels. These include a mix of moderate and difficult options for cyclists to explore.

Are there any dedicated, traffic-free trails for road cycling in Jacksonville?

Yes, a standout feature for road cyclists in Jacksonville is the Jacksonville-Baldwin Rail Trail. This nearly 15-mile paved, shaded pathway offers a traffic-free experience through woodlands and wetlands, suitable for all skill levels. It's a great option for those looking for a linear park experience where they can determine their own distance.

What are some scenic road routes with coastal views in Jacksonville?

For spectacular coastal views, consider routes that incorporate sections of the A1A Ocean Islands Trail. This route can offer designated bike lanes in parts and takes you through North Florida's pristine beaches and state parks. The Timucuan Trail, part of the East Coast Greenway, also provides active cycling opportunities through marshlands and along coastal areas.

What is the best time of year for road cycling in Jacksonville?

Jacksonville's warm climate makes it suitable for road cycling year-round. However, the cooler, drier months from late fall through spring (roughly October to April) are often preferred, offering more comfortable temperatures for longer rides compared to the hotter, more humid summer months.

Are there any challenging road cycling routes in Jacksonville?

Yes, while much of Jacksonville is flat, there are routes designed for more experienced cyclists. The area offers 2 difficult routes, which may feature longer distances or more varied terrain, providing a good challenge for those seeking it. Routes like the A1A Ocean Islands Trail can also be challenging due to their length and exposure.

What natural features or landmarks can I see while road cycling in Jacksonville?

Jacksonville's extensive park system means you'll encounter diverse natural beauty. Routes often pass through areas like the Timucuan Ecological and Historic Preserve with its coastal wetlands, or offer views of the St. Johns River and Intracoastal Waterway. You might also cycle near pristine beaches, maritime forests, and salt marshes, especially around areas like Big Talbot and Little Talbot Islands State Parks.

Are there family-friendly road cycling options in Jacksonville?

Absolutely. The Jacksonville-Baldwin Rail Trail is an excellent choice for families due to its paved, shaded, and traffic-free nature. Its linear design allows families to choose their desired distance, making it accessible and enjoyable for cyclists of all ages and skill levels.

What do other road cyclists say about the routes in Jacksonville?

The road cycling routes in Jacksonville are highly rated by the komoot community, with an average score of 5.0 stars from over 1 review. Over 50 road cyclists have used komoot to explore the area, often praising the diverse terrain and scenic beauty found along the coastal paths, dedicated rail trails, and natural preserves.

Where can I find more information about outdoor activities and biking in Jacksonville?

For additional information on outdoor activities and biking opportunities in the region, you can visit the official Jacksonville tourism website. They offer resources on the city's extensive park system and various recreational options. You can explore more at visitjacksonville.com/things-to-do/outdoors/biking/.

Are there any road cycling routes that are considered moderate difficulty in Jacksonville?

Yes, the majority of road cycling routes in Jacksonville are classified as moderate difficulty, with 5 such routes available. These routes offer a good balance of distance and manageable terrain, suitable for regular cyclists looking for an enjoyable ride without extreme challenges.

Most popular routes around Jacksonville

Hiking around Jacksonville

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