4.5
(122)
4,067
riders
228
rides
Road cycling routes around Shorewood Hills feature a landscape characterized by well-maintained roads and varied terrain, offering options for different skill levels. The area is situated near Lake Monona and Lake Mendota, providing picturesque lakeside vistas that are often incorporated into cycling routes. Riders can expect a mix of gentle gradients and some challenging climbs, with routes passing through local parks and conservancies. The region's infrastructure supports a smooth cycling experience, connecting to broader trail systems for extended rides.
Last updated: May 16, 2026
151
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3.0
(1)
42
riders
63.7km
02:51
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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30
riders
30.7km
01:20
140m
140m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
18
riders
33.8km
01:34
170m
170m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
12
riders
93.4km
03:58
570m
570m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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The first bike counter I saw was in Oklahoma City. This one has a cool meter to it.
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Dawley Conservancy Park is beautiful, covering 42 acres of woodlands, prairies, and wetlands. There are walking trails, abundant wildlife, and active conservation efforts aimed at restoring native plant communities. The park also connects to the Capital City State Trail, making it a scenic hub for local cyclists.
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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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The Pheasant Branch Creek Corridor Trail in Middleton is a short, yet lovely trail that winds through serene wetlands, oak savannas, and prairie fields. It offers stunning views of Pheasant Branch Conservancy and the Capitol skyline.
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On the side of the bike path, there's a - well, what exactly is it? a shrine? - made of little figurines, plants and other random items. Every time you pass, something will be different.
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Glenway Woods is a beautiful, yet somewhat hidden, gem that spans over 10 acres of land. Although it doesn't currently have a park classification, locals have created a few mountain biking trails that wind through the densely wooded area. It's located along the Southwest Commuter Bike Path, providing a scenic route with a touch of nature shaded by the trees.
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Dunn's Marsh is a sizable body of water in the middle of Dawley Conservancy Park. It's right off the side of the Cannonball Path on one side and the Capital City State Trail on the other side.
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Road cycling routes around Shorewood Hills feature a landscape characterized by well-maintained roads and varied terrain. You can expect a mix of gentle gradients and some challenging climbs, with routes often passing through local parks and conservancies. The area is situated near Lake Monona and Lake Mendota, providing picturesque lakeside vistas that are frequently incorporated into the cycling experience.
Shorewood Hills offers a wide selection of road cycling routes, with over 200 options available. These routes cater to various skill levels, from easy loops to more challenging excursions, ensuring there's something for every cyclist.
Yes, Shorewood Hills offers several easy road cycling routes that are suitable for families. These routes often feature well-paved surfaces and pass through scenic parklands, providing a pleasant and accessible experience for riders of all ages. An example is the Dawley Conservancy Park – The Hop Garden loop from Dane County, which is rated as easy and offers scenic views.
Shorewood Hills is known for its scenic loop routes that often incorporate beautiful lakeside views. Popular options include the "Bench With View of Lake Monona – Monona Terrace View loop" and the Glenway Woods – Monona Terrace View loop from Glen Oak Hills, which leads through Glenway Woods and offers views of Lake Monona.
Yes, some road cycling routes in Shorewood Hills connect to broader trail systems, offering opportunities for longer rides. For instance, the Dawley Conservancy Park – Military Ridge State Trail loop from Dane County connects to the Military Ridge State Trail, providing a moderate path through varied landscapes.
Many road cycling routes in Shorewood Hills offer picturesque lakeside vistas of Lake Monona and Lake Mendota. You can also pass by natural features like Glenway Woods and University of Wisconsin–Madison Arboretum. The area also features parks and conservancies, enhancing the natural beauty of your ride.
Absolutely. Beyond the routes themselves, you can explore significant natural and historical sites. The Picnic Point Mound Group, an ancient burial site, offers a cultural and natural point of interest. Additionally, the Olbrich Botanical Gardens, with its diverse themed gardens, provides a beautiful and serene environment to visit.
The best time for road cycling in Shorewood Hills is typically during the warmer months, from spring through fall, when the weather is mild and the natural scenery is at its peak. The well-maintained roads are generally clear, and the lakeside views are particularly enjoyable during these seasons.
The road cycling experience in Shorewood Hills is highly rated by the komoot community, with an average score of 4.5 stars. Reviewers often praise the area's diverse network of routes, the picturesque lakeside scenery, and the well-maintained road surfaces that make for a smooth and enjoyable ride.
Yes, while there are many easy and moderate routes, Shorewood Hills also offers more challenging excursions for experienced cyclists. These routes can feature significant climbs and longer distances, sometimes exceeding three hours with considerable elevation gain, requiring good to very good fitness.
For information regarding cycling permits in Dane County, Wisconsin, it's best to consult local government resources. Wisconsin's state and county road systems are classified for bicycling conditions, and local bicycle maps are available. You can find more details on the official Wisconsin Department of Transportation website: wisconsindot.gov.
Public transport options are available in the Madison area, which can help access various bike trails. For specific routes and schedules to trailheads like the Capital City State Trail, it's recommended to check the local Madison Metro Transit services for the most current information on bus routes and stops.
While Shorewood Hills itself is a residential village, its proximity to Madison means there are numerous cafes and pubs within a short cycling distance. Many routes will take you close to areas where you can find refreshments, especially in the broader Madison area.


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