4.5
(183)
2,183
riders
100
rides
No traffic touring cycling routes around Shorewood Hills are characterized by their proximity to Lake Mendota and integration into Madison's extensive network of paved trails. The area features diverse landscapes, including lakeside vistas, wooded conservancies, and residential areas with notable architecture. These routes often follow well-maintained paths, providing a mix of flat sections and gentle elevation changes suitable for touring cyclists.
Last updated: July 2, 2026
4.5
(2)
20
riders
11.9km
00:43
70m
70m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
8
riders
20.1km
01:13
80m
80m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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10
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
4.0
(1)
3
riders
17.9km
01:04
100m
100m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
4
riders
12.7km
00:48
100m
100m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Shorewood Hills
In loving memory of Christopher "Red" Vogts February 17th, 1987 - February 8th, 2013 "When despair for the world grows in me and I wake in the night at least sound in fear of what my life and my children's lives may be, I go and lie down where the wood drake rests in his beauty on the water, and the great heron feeds. I come into the peace of wild things, who do not tax their lives with forethought of grief. I come into the presence of still water. And I feel above me the day. Blind stars, waiting with their light. For a time, I rest in the grace of the world, and lam FREE." Do It Real Big.
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This small patch of woods sits right along the Southwest Commuter Path in Madison. Stay on the gravel path and walk the hiking trails as the signs suggest—bikes can cause erosion in this sensitive area. Enjoy the trails winding around old oaks, giving you a chance to stretch your legs under the trees before hopping back on your bike.
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Key Takeaways: What it is: A natural sandstone cave on the shore of Lake Mendota in Madison. The Legend: Famously (but inaccurately) said to be a hiding spot for Chief Black Hawk in 1832. The Reality: A natural shelter likely used by the Ho-Chunk and other Native peoples for centuries. Current Status: CLOSED TO THE PUBLIC. The entrance is permanently sealed for safety reasons due to the high risk of collapse. You can still view the area from a boat on the lake, but you cannot enter the cave.
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Modern History and Current Status For over a century, the cave was a popular destination for boaters, hikers, and University of Wisconsin students. However, the soft sandstone that allowed its formation also makes it inherently unstable. Due to significant erosion and several partial collapses, the cave became extremely dangerous. To ensure public safety, the entrance has been sealed off with a large metal grate.
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The Historical and Geological Reality Geology: The cave is not man-made. It was naturally formed over thousands of years by the wave action of Lake Mendota eroding the soft Cambrian sandstone bluff. True History: While Chief Black Hawk almost certainly never used it, the cave was undoubtedly known and used by Native Americans for centuries, most notably the Ho-Chunk people, who have inhabited the Madison area for generations. It would have served as a valuable temporary shelter from the elements for those fishing, hunting, or traveling along the lake.
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The Legend The cave's name comes from the famous Sauk leader, Chief Black Hawk (Makataimeshekiakiak). The prevailing legend states that during the Black Hawk War of 1832, after his band was defeated at the Battle of Wisconsin Heights, Chief Black Hawk fled and hid in this cave to evade the pursuing U.S. militia before making his escape across the Wisconsin River. However, historians widely agree that this story is very unlikely to be true. The timeline and geographical location of the cave do not match the documented route of Black Hawk's retreat. The legend likely emerged later in the 19th century, as settlers romanticized the war and attached the famous leader's name to a prominent local landmark.
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Blackhawk's Cave is a well-known historical landmark located on the southern shore of Lake Mendota in Madison, Wisconsin. It's a natural sandstone cave that holds a significant place in local folklore, though its popular story is more legend than historical fact.
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There are over 100 dedicated no-traffic touring cycling routes around Shorewood Hills, with the vast majority (78) being easy, making them accessible for various fitness levels. You'll find a good selection of moderate routes (22) and even one challenging option for experienced cyclists.
Yes, Shorewood Hills offers many easy, traffic-free routes perfect for beginners and families. An excellent option is the Southwest Commuter Path – Glenway Woods loop from Dane, which provides a gentle ride through scenic areas without vehicle interference. The region's extensive network of paved paths, like the Blackhawk Path and Capital City State Trail, are generally very family-friendly.
The no-traffic touring cycling routes in Shorewood Hills offer a diverse range of landscapes. You can expect scenic lakeside vistas, especially around Lake Mendota, as well as rides through tree-filled residential areas, parks, and conservancies. Many routes incorporate sections of the UW Arboretum, providing prairie views and woodland scenery. The area is also known for its active conservation efforts, so you might spot various bird species and wildlife.
Yes, many of the no-traffic touring cycling routes in Shorewood Hills are designed as loops. For example, the Glenway Woods – Lake Mendota loop from Dane offers a pleasant circular ride, allowing you to experience different views without retracing your path. These loops are ideal for exploring the varied terrain and attractions of the region.
While cycling, you can discover several interesting attractions. Keep an eye out for the unique architecture, including structures by Frank Lloyd Wright. Natural highlights include the shores of Lake Mendota, and you might pass by historical sites like the Picnic Point Mound Group or the Eagle Heights Mound Group (DA130). The University of Wisconsin–Madison Arboretum is also nearby, offering beautiful natural settings.
Shorewood Hills is well-integrated into Madison's infrastructure. Madison, as a Platinum-Level Bike-Friendly Community, has a strong cycling culture and an extensive network of trails that connect vibrant neighborhoods. While specific public transport details for each trailhead aren't listed here, the general connectivity of the area suggests good access to various starting points via Madison's public transportation system. For detailed public transport information, it's best to consult local Madison transit resources.
Given Shorewood Hills' location within the Madison area, many trailheads and access points for the extensive bike path network (like the Capital City State Trail and Blackhawk Path) will have designated parking areas. For specific routes, such as the Lakeshore Nature Preserve – Raymer's Cove loop from Dane, you'll typically find parking available near the starting points or within adjacent parks. It's advisable to check local parking regulations for specific trail access points.
The komoot community highly rates the touring cycling experience in Shorewood Hills, with an average score of 4.34 stars. Reviewers often praise the peaceful, traffic-free nature of the routes, the beautiful lakeside views, and the well-maintained paved surfaces. The ability to connect to Madison's broader trail network and explore diverse landscapes, from urban parks to natural conservancies, is also frequently highlighted.
Absolutely. Shorewood Hills is situated directly on Lake Mendota, so many routes offer stunning lakeside views. The Howard Temin Lakeshore Path – Lake Mendota loop from Dane is a prime example, providing continuous scenic vistas of the lake. You'll also find routes that pass through McKenna Park (Shorewood Hills Beach), offering direct access to the lake.
Yes, the region is rich in natural areas. Routes frequently pass through or near conservancies and parks. For instance, the Howard Temin Lakeshore Path – Lake Mendota loop from Dane (a longer version) allows you to experience the natural beauty of the Lakeshore Nature Preserve, which is part of the UW-Madison campus. Other areas like Glenway Woods and Dunn's Marsh also offer opportunities to cycle through serene natural settings.


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