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Routes
Road cycling routes
United States
Wisconsin
Dane County

Cross Plains

The best road cycling routes around Cross Plains

4.0

(11)

519

riders

34

rides

Road cycling routes around Cross Plains Wisconsin traverse a landscape shaped by glacial history, featuring a convergence of glaciated and unglaciated terrain. The region is characterized by rolling hills, expansive farmlands, and diverse ecosystems including oak savanna, wetlands, and prairies. This topography provides varied routes, including both climbs and descents through scenic countryside. The area's natural features contribute to a dynamic road cycling experience.

Best road cycling routes around Cross Plains

  • The most popular road cycling route is Esser Pond…

Last updated: August 22, 2026

38

riders

#1.

Esser Pond – Coffee and ice cream! loop from Cross Plains

42.7km

02:04

420m

420m

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

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Moderate

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

Moderate
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4.3

(3)

6

riders

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

Moderate

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

Moderate

7

riders

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Popular around Cross Plains

Hiking around Cross Plains

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Cycling around Cross Plains

Tips from the Community

tcbscott
October 9, 2025, Cyclist Counter on Capital City Trail

The first bike counter I saw was in Oklahoma City. This one has a cool meter to it.

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MADISON PARK & PLEASURE DRIVE ASSOCIATION Duting the 19th Century, Willow Creek marked the western edge of the University of Wisconsin campus and the end of University Drive. In 1892, at the suggestion of Prol Edward TOwen, a commitice of public spirited citizens constructed a "pleasure drive" west from this point, opening the privately owned Lake Mendota shoreline for public enjoyment. As part of this project, the first Willow Creek bridge was built The drive, intended for saddle horses, carriagesy and bicycles, crossed University Bay Marsh ascended Eagle Heights and followed the shoteline to Merill Springs (Spring Harbor in 1894 the committee became the Madison Park and Pleasure Drive Association under the leadership of Jonn MOline Relying on voluntary contributions- this renowned organization established other pleasure drives as well as tenney, Vilas, and Brittingham Park 1938

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The Capital City State Trail is a 17-mile paved multi-use path open year-round. A state trail pass is required to bike the nine-mile portion of the trail that passes through the Capital Springs E-way south of Madison between Verona Road and Nob Hill near Industrial Drive, but the remainder is free to access.

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Alex
April 26, 2025, Nissaru's

Classic Wisconsin dive bar right on the bike trail. Excellent beer and pizzas - a great stop off with an incredibly friendly staff for your next bike trip. There are bike racks on premises.

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Nice bridge that takes you over Willow Creek. The bridge is part of Howard Temin Lakeshore Path.

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Monona Terrace is a large convention center on Lake Monona. There is a mulit-use path that takes you along the lake and through the grounds of the convention center.

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very beautiful at the lake shore near Monona Terrace

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Lisa
November 16, 2023, Monona Terrace View

If you want an unbeatable view of the Capitol building dome — not to mention the rest of Madison — it's well worth tying up your bike and popping up to this rooftop terrace on the convention building.

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Frequently Asked Questions

How many road cycling routes are available in Cross Plains?

There are over 30 road cycling routes around Cross Plains, offering a diverse range of options for cyclists. These routes are rated by the komoot community with an average score of 4.0 stars.

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

Cross Plains offers a varied landscape shaped by glacial history, featuring rolling hills, expansive farmlands, and a mix of glaciated and "driftless" areas. This topography provides undulating roads with both challenging climbs and rewarding descents through scenic countryside.

Are there routes suitable for beginners or those looking for an easier ride?

Yes, Cross Plains has 9 easy road cycling routes. These routes often feature mostly paved surfaces, minimal turns, and showcase rolling farmland without significant elevation gains, making them ideal for new road cyclists or those seeking a more relaxed ride.

What are some challenging road cycling routes for experienced riders?

For experienced riders seeking a challenge, routes like Barlow Road climb loop from Holmes Preserve offer significant elevation gain and varied terrain. The region's glacial landforms contribute to routes with up to 1500 feet of elevation gain over longer distances.

Are there any scenic viewpoints or natural features to look out for along the routes?

Yes, the region is rich in natural beauty. Cyclists can enjoy views of the driftless area, glacial landforms, and expansive farmlands. Notable natural features include the Black Earth Creek area, which you can explore on routes like the Roadbike loop from Black Earth Creek Fishery Area. You might also spot highlights like Indian Lake or the Farmstead overlook.

Can I find loop routes for road cycling in Cross Plains?

Many of the road cycling routes in Cross Plains are designed as loops, allowing you to start and end at the same point. An example is the popular Esser Pond loop from Town of Cross Plains, which offers views of rolling farmland and countryside.

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

The best time for road cycling in Cross Plains is typically during the spring, summer, and fall months when the weather is mild and the scenery is vibrant. The region's rolling hills and farmlands are particularly beautiful during these seasons.

Are there family-friendly road cycling options in Cross Plains?

Yes, Cross Plains offers routes suitable for families. These typically feature mostly paved surfaces and lower elevation gains, making them accessible for various skill levels. The local parks and conservancy lands also provide tranquil settings for outdoor activities.

What do other road cyclists enjoy most about cycling in Cross Plains?

The komoot community highly rates road cycling in Cross Plains, with an average score of 4.0 stars. Cyclists often praise the diverse terrain, the scenic views of rolling hills and farmlands, and the well-maintained routes that cater to various fitness levels.

Where can I find parking for road cycling routes in Cross Plains?

Parking is generally available at various points throughout the Cross Plains area, including near trailheads and local parks. For specific routes, it's advisable to check the route details on komoot for recommended starting points and parking information.

Are there any historical sites or landmarks to explore near the cycling routes?

While cycling, you might encounter historical elements such as the Farmhouse ruins. The area also has a rich glacial history, with the Ice Age National Scenic Trail passing through, underscoring the region's unique geological past.

Can I find places to eat or stay in Cross Plains after a ride?

Cross Plains, as a village, offers local amenities including cafes and pubs where cyclists can refuel. For accommodation, there are options within the village and surrounding areas to suit different preferences, making it convenient for multi-day cycling trips.

Most popular routes around Cross Plains

Easy hikes around Cross Plains

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Browse the best Road cycling routes in other regions.

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