The best cycling routes around Waukesha
4.9
(41)
278
riders
17
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.
Best touring cycling routes around Waukesha
- The most popular touring cycling route is Glacial Drumlin State Trail, a 35.1 miles (56.5 km) trail that takes 3 hours 34 minutes to complete. This moderate route follows a former railway, offering a generally flat and scenic path.
- Another top favourite among local touring cyclists is Fox River Trail, an easy 15.9 miles (25.6 km) path. This trail runs alongside the Fox River, providing riverside views and a smooth surface.
- Local touring cyclists also love the Wooden Bridge Over Trail loop from Waukesha, a 12.3 miles (19.8 km) trail leading through varied local scenery, often completed in about 1 hour 8 minutes.
- Touring cycling around Waukesha is defined by river corridors, converted rail trails, and local park loops. The network offers options for different ability levels, from easy family friendly bike trails Waukesha to long distance cycling routes Waukesha.
- The routes in Waukesha are highly rated by the komoot community with an average score of 4.9 stars from over 30 reviews. More than 200 touring cyclists have used komoot to explore Waukesha's varied terrain.
Last updated: September 27, 2026
5.0
(3)
30
riders
56.5km
03:34
200m
200m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(3)
8
riders
25.6km
01:28
80m
80m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
19
riders
69.5km
04:00
220m
220m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(4)
24
riders
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
21
riders
19.8km
01:08
80m
80m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Waukesha
Tips from the Community
For those entering and leaving the Milwaukee City centre, there is a vast network of bike paths throughout the Milwaukee area. The paths themselves are a great way to navigate the area, however the quality of the asphalt in the cities is debatable. The city officials of the city should perhaps take better care of these cycleways, as they are developing rather larger potholes here and there, I would only recommend using tyres > 28mm width. The city in itself is very bikeable.
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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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As you ride the Glacial Drumlin State Trail past the UWM Waukesha Field Station, you’ll pass prairies, wetlands, and even an old kiln. It’s a fun spot to slow down, spot some wildlife, or take a quick detour on the Field Station trails before jumping back on the main route.
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The Hank Aaron State Trail is a 14-mile paved shared-use path running through the heart of Milwaukee with great views of the Milwaukee River and the city skyline.
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View of the Milwaukee river as it crosses under the Hoan Bridge at a very active boat landing.
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Frequently Asked Questions
How many touring cycling routes are available in Waukesha?
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.
Are there easy touring cycling routes suitable for beginners or families in Waukesha?
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.
Are there any long-distance touring cycling routes in Waukesha?
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.
What scenic viewpoints or natural attractions can I find along the touring cycling routes?
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.
Are there any circular touring cycling routes around Waukesha?
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.
What do other touring cyclists enjoy most about cycling in Waukesha?
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.
Can I bring my dog on the touring cycling routes in Waukesha?
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.
What is the best time of year to cycle the Glacial Drumlin State Trail?
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.
Are there any less-known or 'hidden gem' touring cycling routes in Waukesha?
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.
Where can I find parking for the touring cycling routes in Waukesha?
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.
Are there options for winter cycling in Waukesha?
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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