The best road cycling routes in Wisconsin

The Lake Monona Loop and Capital City Trail offers a dynamic road cycling experience, combining the best of Madison's urban and natural landscapes. You'll pedal past the Frank Lloyd Wright-designed Monona Terrace Convention Center and enjoy breathtaking views of Lake Monona and the State Capitol dome, before transitioning into the diverse wetlands and prairies of the Capital Springs State Park and Recreation Area. The route provides a unique cultural and aesthetic journey, with continuous water views and opportunities for wildlife spotting.

This moderate 26.4-mile (42.5 km) route features 549 feet (167 metres) of elevation gain, typically taking about 2 hours and 1 minute to complete. While generally accessible, expect some short but steep hill climbs on the Monona side, providing a good workout. A state trail pass is required for certain sections of the Capital City Trail if you are 16 or older, so be sure to check requirements before you go.

Connecting to numerous other trails, including the Lower Yahara River Trail with its impressive non-motorized boardwalk over water, this route is a crucial hub for Madison cyclists. It's a fantastic option for those seeking a varied ride that blends city landmarks with natural beauty, suitable for a wide range of skill levels looking for a substantial, scenic outing.

The Glacial Drumlin State Trail offers a delightful ride through Wisconsin's varied landscapes, showcasing the region's unique glacial history. As you cycle, you'll pass through tranquil farmlands, dense woodlands, and expansive wetlands, often spotting wildlife like deer and sandhill cranes. The route features impressive crossings over the Crawfish and Rock Rivers, and you'll even traverse a quarter-mile-long bridge over Rock Lake near Lake Mills, providing picturesque views.

Planning your trip is straightforward, but remember that a state trail pass is required for cyclists aged 16 and older. While mostly off-road, there's a 1.5-mile on-road section northeast of Jefferson that requires using public roads, so be mindful of traffic and some gentle hills there. The trail connects numerous small towns, providing convenient access to food and facilities, making it easy to refuel and relax along your journey.

This easy road cycling route spans 30.1 miles (48.5 km) with a minimal 628 feet (191 metres) of elevation gain, typically taking around 1 hour and 56 minutes to complete. It's built on an abandoned railway corridor, which explains its flat profile and the presence of original wood-planked bridges. The varied surface, from paved asphalt to crushed limestone, means a hybrid or cross bike might be more comfortable, though road bikes can certainly manage, especially on the eastern paved sections.

The Oak Leaf Trail: Milwaukee River and Lake Loop offers a fantastic road cycling experience, guiding you through a dynamic blend of urban green spaces and waterfront views. You'll pedal along smooth asphalt paths, enjoying the refreshing breeze off Lake Michigan near Bradford Beach and the serene flow of the Milwaukee River. This easy route is a perfect way to explore the city's natural beauty without strenuous climbs, providing a relaxing atmosphere for all cyclists.

Planning your ride is straightforward, as the trail is highly accessible with many entry points throughout Milwaukee. No special permits are needed, and the route is well-maintained, making it suitable for a spontaneous outing. Given its popularity, especially on weekends, an early morning start is recommended to fully enjoy the peaceful stretches and avoid peak traffic on the multi-use path.

This loop is a key part of Milwaukee County's extensive Oak Leaf Trail system, which boasts over 135 miles of trails. It's a true urban green corridor, connecting various parks and attractions like the Milwaukee Art Museum, and offering a unique perspective on the city's history and development. The gentle 25.9-mile (41.7 km) distance, minimal 472 feet (144 metres) of elevation gain, and estimated 1 hour and 44 minutes duration make it an ideal choice for beginner road cycling routes in Milwaukee or a family-friendly cycling adventure.

The Glacial Drumlin and Lake Country Trail Loop offers road cyclists a delightful tour through southeastern Wisconsin's diverse landscapes. This easy 21.6-mile (34.8 km) route, with 798 feet (243 metres) of elevation gain and an estimated duration of 1 hour and 26 minutes, combines the unique glacial formations and wetlands of the Glacial Drumlin State Trail with the scenic lake views of the Lake Country Trail. You'll encounter everything from tranquil farmlands and dense woodlands to the impressive quarter-mile bridge over Rock Lake, making for a varied and engaging ride. The Lake Country Trail also provides stunning vistas of lakes like Silver Lake and Nagawicka Lake, along with the notable Veterans Memorial Riverwalk in Delafield. It's a perfect choice for those seeking a rewarding, accessible road cycling route.

Planning your ride is straightforward, with numerous trailheads offering parking and amenities along both the Glacial Drumlin and Lake Country Trails. The loop connects seamlessly at Delafield via Cushing Park Road, making navigation simple. While generally an easy ride, be aware of some gentle grades and a few short, punchy climbs on the Lake Country Trail. The best time to enjoy this loop for road cycling is typically during the spring, summer, and fall months when the weather is mild and the trails are in prime condition.

What makes this loop truly stand out is its blend of natural beauty and historical significance, tracing former railroad beds through areas shaped by glaciers. The Glacial Drumlin State Trail is named for the distinctive drumlins, offering a unique geological backdrop, while the Lake Country Trail provides glimpses of Wisconsin's beautiful lake country. Both trails are part of a broader network, hinting at future connections and making this loop a central piece of the region's cycling infrastructure. It's an excellent option for family-friendly cycling, offering a mix of paved and crushed limestone surfaces that cater to various preferences.

The Bugline and Lake Country Trail Loop offers road cyclists a varied journey through Waukesha County, combining two distinct paved trails. You'll experience the flatter, shaded Bugline Trail, winding past rural landscapes, Lannon Quarries, and the Bark River, before transitioning to the more challenging, rolling terrain of the Lake Country Trail, which provides scenic views of Nagawicka Lake and Pewaukee Lake, and passes through the historic city of Delafield. It's a great option if you enjoy diverse scenery and a mix of gentle and hilly sections.

This moderate road cycling route covers 42.5 miles (68.3 km) with 1065 feet (325 metres) of elevation gain, typically taking around 2 hours and 52 minutes to complete. While mostly on dedicated trails, be prepared for necessary on-road connections, including a section near Nemahbin Lakes with a narrow shoulder that might challenge less experienced riders. Parking and amenities are available at various trailheads along the Lake Country Trail, and Delafield offers convenient spots for a break.

This loop is a fantastic way to explore the "Route of the Badger" trail network, showcasing the natural and developed landscapes of Southeast Wisconsin. The contrast between the gentle Bugline and the more strenuous Lake Country Trail makes for an engaging ride, highlighting former rail-trail paths and offering glimpses of the region's lakes and charming towns. It's a substantial ride for those looking to spend a good part of their day exploring.