4.9
(41)
241
riders
16
rides
Touring cycling around Waukesha features a landscape characterized by river valleys, converted rail trails, and a mix of open and wooded areas. The region offers varied terrain, including the long-distance Glacial Drumlin State Trail, which follows a former railway line. Gentle elevation changes are present, providing accessible routes for different skill levels. The area's geology contributes to a generally smooth cycling experience along its established paths.
Last updated: November 7, 2026
5.0
(3)
29
riders
56.5km
03:34
200m
200m
Moderate bike ride. Good fitness required. Mostly paved surfaces.
5.0
(3)
8
riders
25.6km
01:28
80m
80m
Easy bike ride. Mostly paved surfaces.

5.0
(4)
24
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces.
5.0
(1)
13
riders
35.6km
02:02
120m
120m
Moderate bike ride. Good fitness required. Mostly paved surfaces.
5.0
(3)
8
riders
34.4km
02:03
230m
230m
Moderate bike ride. Good fitness required. Mostly paved surfaces.
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Just east of Wales, Wisconsin is this bridge over the trail. This is where the climb ends as you are heading west.
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A glacial drumlin is a teardrop-shaped hill of sediment left behind when a glacier grinds its way past. This trail, on the other hand, is a thread of about 52 miles that connects ten different towns in Wisconsin, sometimes passing through beautiful green corridors like this one.
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This riverside park's primary focus is the Waukesha Parade Memorial, dedicated to lives lost and support of those surviving from the 2021 Christmas Parade Tragedy.
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Take in a beautiful uplift of nature in this 257-acre park: You'll find wildflowers, mature forest and wetlands. Keep your eye out for wildlife, too.
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Connecting Oconomowoc to Nemahbin Lakes, the Lake Country Trail offers open views and lakeside scenery. It’s a fun, low-traffic stretch with a mix of urban and countryside, passing by big barns along the way.
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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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There are over 15 touring cycling routes available in Waukesha on komoot, ranging from easy to moderate difficulty. These routes have been explored by more than 200 touring cyclists.
Yes, Waukesha offers several easy touring cycling routes perfect for beginners and families. The Fox River Trail is a great option, running alongside the Fox River with a smooth surface. Another easy choice is the Wooden Bridge Over Trail loop from Waukesha, which offers varied local scenery.
Yes, the Glacial Drumlin State Trail is a prominent long-distance option. This moderate 35.1-mile (56.5 km) trail follows a former railway line, providing a generally flat and scenic path through the region's landscape.
Waukesha's touring cycling routes offer access to various natural attractions. You might encounter highlights like Nagawicka Lake or the Lapham Peak Observation Tower, which provides expansive views. The trails themselves often feature river corridors and wooded areas.
Yes, there are several loop options. The Wooden Bridge Over Trail loop from Waukesha is a popular 12.3-mile (19.8 km) route. Another option is the Bike loop from Meadowbrook Park & Ride, offering a moderate 34.4 km ride.
The touring cycling routes in Waukesha are highly rated by the komoot community, with an average score of 4.9 stars. Reviewers often praise the varied terrain, from river valleys to converted rail trails, and the accessibility for different skill levels.
Many state trails and local paths in Wisconsin, including those around Waukesha, are dog-friendly, typically requiring dogs to be on a leash. Always check specific trail regulations before heading out, especially for state trails which may have specific rules or require a state trail pass.
The Glacial Drumlin State Trail is generally best enjoyed from spring through fall. Spring offers lush greenery, while autumn provides vibrant fall foliage. Summer is also popular, but be prepared for warmer temperatures and potential humidity. Winter cycling is possible for experienced riders, but conditions can be challenging with snow and ice.
While popular routes like the Glacial Drumlin State Trail are well-loved, exploring routes such as the Wooden Bridge Over Trail – Grede Park (Parade Memorial) loop from Meadowbrook Park & Ride can offer a more localized experience through varied scenery, away from the busiest sections.
Many trailheads for state trails and local parks in Waukesha County offer designated parking areas. For instance, routes often start or pass by locations like Meadowbrook Park & Ride, which provides parking facilities. It's advisable to check the specific starting point of your chosen route for detailed parking information.
While many trails are primarily used in warmer months, some paths in Waukesha may be suitable for winter cycling, especially if they are plowed or packed down. However, conditions can vary greatly with snow and ice, so it's essential to check local trail conditions and be prepared with appropriate gear for cold weather and potentially slippery surfaces.


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