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Road cycling routes
United States

Wisconsin

The best road cycling routes in Wisconsin

4.5

(459)

13,424

riders

1,071

rides

Road cycling routes in Wisconsin traverse a landscape shaped by glacial activity, featuring distinctive landforms and a diverse natural environment. The state offers extensive paved routes through regions like the unglaciated Driftless Area with its rolling hills and deep valleys, and the Kettle Moraine State Forest. Cyclists encounter numerous lakes, rivers, and Great Lakes shorelines, alongside vast forests and prairie remnants. Many routes utilize converted railway lines, providing flat and well-maintained paths ideal for road cycling.

Best road cycling routes in Wisconsin

  • The most popular road cycling route is Madison – Lake Menona, Wingra and Mendota, a 26.4 miles (42.5 km) moderate trail that takes 2 hours 1 minute to complete. This route circles Madison's lakes, offering urban and natural scenery.
  • Another top favourite among local road cyclists is Dousman to Waukesha via Glacial Drumlin State Trail — Waukesha County, an easy 30.1 miles (48.5 km) path. It follows a former railway line, providing a relatively flat ride through varied landscapes.
  • Local road cyclists also love the Oak Leaf Trail & Lake Michigan loop — Milwaukee, a 25.9 miles (41.7 km) trail leading through urban parks and along the Lake Michigan shoreline, often completed in about 1 hour 44 minutes.
  • Road cycling in Wisconsin is defined by extensive rail-to-trail networks, the rolling hills of the Driftless Area, and scenic routes along lake shorelines. The network offers options for various ability levels, from easy, flat paths to more challenging routes with significant elevation changes.
  • The routes in Wisconsin are highly rated by the komoot community with an average score of 4.5 stars from over 400 reviews. More than 13,000 road cyclists have used komoot to explore Wisconsin's varied terrain.

Last updated: April 24, 2026

66

riders

#1.

Lake Monona Loop and Capital City Trail

42.5km

02:01

170m

170m

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

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Moderate

71

riders

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

Easy
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3.0

(1)

42

riders

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

Easy

5.0

(1)

27

riders

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

Easy

5.0

(1)

7

riders

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

Moderate

12

riders

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

Moderate

10

riders

83.3km

04:31

770m

770m

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

Moderate

11

riders

95.3km

04:11

290m

290m

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

7

riders

51.2km

02:07

250m

250m

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

Moderate
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Popular around Wisconsin

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Tips from the Community

oliviakellis
June 29, 2025, Veterans Park

The park is a tribute to veterans and a cherished community gathering area. This is a good spot to take a break and enjoy the serene surroundings in this urban park.

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Billed as "the most accessible beach in America" and as one of the cleanest beaches in the country, this spot can get pretty busy. It's free for day use and has a couple of on-site spots for food and refreshments.

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Sue
January 25, 2025, Milwaukee Art Museum

Situated on the city's beautiful waterfront, The Milwaukee Art Museum is the largest in the state. It features a collection of nearly 32,000 artworks across four floors, including modern and contemporary pieces, as well as notable architecture. The collection spans from ancient times to the present and includes European and American paintings, sculptures, prints, drawings, decorative arts, photographs, and folk art.

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The University of Wisconsin–Madison Arboretum is a research and ecological protection site in Madison. It has several miles of trails and quiet roads that weave through the beautiful wood land. The centerpiece of the area is Lake Wingra.

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The Meadowbrook Trail, along the Route of the Badger, is 2.4 miles and winds through a blend of neighborhoods and business districts. This paved route offers a mostly open path with sparse shade, bordered by a broad grassy median away from the road. Cyclists should pack extra water for the ride to stay hydrated.

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The Cushing Park Road Recreational Trail, part of the Route of the Badger, stretches for 3 miles. Though short, it serves as a crucial link in the regional trail system, connecting the Lake Country Recreation Trail to the north and the Glacial Drumlin State Trail to the south. Cyclists can also access the Ice Age Trail from this pathway.

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The park is a tribute to veterans and a cherished community gathering area. This is a good spot to take a break and enjoy the serene surroundings in this urban park.

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The Five Points Historic District in Waukesha, at the intersection of Broadway, Main St., and Grand Ave, showcases the history of some of the city's most iconic buildings. Post-1857, the area transitioned from small wooden structures to grand Waukesha Lannon limestone buildings, creating a cohesive streetscape. Italianate and Queen Anne styles, with their distinctive turrets, are prominent, especially on corner sites. South Street, with its mix of styles and uses, remained residential into the 1880s.

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Frequently Asked Questions

How many road cycling routes are available in Wisconsin?

Wisconsin offers a vast network for road cyclists, with over 1,000 routes available on komoot. These routes cater to various skill levels, from easy, flat paths to more challenging rides with significant elevation changes.

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

Wisconsin's road cycling routes traverse diverse landscapes. You'll find paths through areas shaped by glacial activity, featuring distinctive landforms like those in the Kettle Moraine State Forest. The southwestern Driftless Area offers picturesque rolling hills and deep valleys. Many routes also utilize converted railway lines, providing flat and well-maintained surfaces. Expect to encounter numerous lakes, rivers, Great Lakes shorelines, and lush forests.

Are there easy road cycling routes suitable for beginners or families in Wisconsin?

Yes, Wisconsin is well-suited for beginners and families, with over 500 easy routes available. Many of these are former railway lines converted into recreational trails, offering relatively flat and well-maintained surfaces. A great example is the Dousman to Waukesha via Glacial Drumlin State Trail, which is an easy 30.1-mile path through varied landscapes.

What are some of the most scenic road cycling routes in Wisconsin?

Wisconsin boasts many scenic routes. The Madison – Lake Menona, Wingra and Mendota route offers urban and natural scenery as it circles Madison's lakes. For coastal views, the Oak Leaf Trail & Lake Michigan loop in Milwaukee leads through urban parks and along the Lake Michigan shoreline. The Great River Road (Highway 35) also provides spectacular views of bluffs and the Mississippi River.

Are there long-distance road cycling routes in Wisconsin?

Yes, Wisconsin offers several options for longer road cycling adventures. Routes like the Janesville to Jefferson – Glacial River Trail span over 59 miles (95 km), providing an extended ride through the state's diverse scenery. The Sauk County loop from Sauk City is another substantial route, covering over 51 miles (83 km).

Can I find loop road cycling routes in Wisconsin?

Yes, many road cycling routes in Wisconsin are designed as loops, allowing you to start and end in the same location. Examples include the Route of the Badger loop via Cushing Park Road Recreational Trail in Waukesha County and the scenic Baraboo, Merrimac, and Lodi loop via the Ferry.

What natural features or landmarks can I see along Wisconsin's road cycling routes?

Wisconsin's routes offer a wealth of natural beauty and landmarks. You can encounter unique glacial formations, such as those highlighted by the Ice Age National Scenic Trail. The Driftless Area features stunning rolling hills and deep valleys. Along various routes, you might pass by the Willow Falls, explore the University of Wisconsin–Madison Arboretum, or witness the impressive Devil's Doorway Rock Formation.

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

The best time for road cycling in Wisconsin is generally from spring through fall, when the weather is mild and the natural scenery is at its peak. Spring brings lush greenery, while fall offers vibrant foliage, especially in areas like Door County or the Driftless Area. Summer is also popular, but be mindful of warmer temperatures and potential for more crowded trails.

Are there road cycling routes in Wisconsin that follow former railway lines?

Yes, Wisconsin is renowned for its extensive network of rail-to-trail conversions, which are ideal for road cycling. These trails, such as the Glacial Drumlin State Trail, are often flat, well-maintained, and pass through varied landscapes, offering a smooth and enjoyable ride. The state has been a pioneer in converting abandoned railway lines into recreational paths.

Where can I find parking for road cycling trails in Wisconsin?

Many state trails and parks in Wisconsin offer designated parking areas at trailheads. For specific routes, it's advisable to check the details of the individual trail or park you plan to visit, as parking availability can vary. State parks and forests often have visitor centers with parking facilities.

What do other road cyclists enjoy the most about road cycling in Wisconsin?

The road cycling experience in Wisconsin is highly rated by the komoot community, with an average score of 4.5 stars. Cyclists frequently praise the state's diverse and scenic landscapes, the extensive network of well-maintained trails (especially the rail-to-trails), and the variety of routes that cater to all ability levels. The combination of natural beauty and bike-friendly infrastructure makes it a favorite destination.

Are there road cycling routes that pass through state parks in Wisconsin?

Yes, many of Wisconsin's state parks and forests offer excellent road cycling opportunities. Parks like Peninsula State Park, Devil's Lake State Park, and Kettle Moraine State Forest feature diverse trail systems that include paved paths suitable for road bikes, allowing cyclists to explore the natural beauty within these protected areas.

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Check out more Road cycling routes throughout Wisconsin below and find the perfect route in your destination.

Outagamie CountyWaupaca CountyLa Crosse CountyRichland CountyTrempealeau CountyIron CountyBuffalo CountyDane CountySauk CountyVilas CountyWashington CountyBayfield CountyChippewa CountyPepin CountyVernon CountyLafayette CountySt. Croix CountyJuneau CountyGreen Lake CountyKenosha CountyWashburn CountyFond Du Lac CountyRock CountyEau Claire CountyPolk CountyRacine CountyDouglas CountyMarquette CountyBrown CountyIowa CountyWaukesha CountyGrant CountyColumbia CountyJefferson CountyWinnebago CountyOzaukee CountyWaushara CountyPierce CountyGreen CountyCalumet CountyForest CountyWalworth CountySawyer CountyDodge CountyMilwaukee CountyManitowoc CountyLincoln CountyDoor CountyOneida CountySheboygan CountyMarathon CountyChequamegon-Nicolet National Forest

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