5.0
(7)
164
riders
16
rides
Road cycling routes around Caledonia, Wisconsin, traverse a landscape characterized by rolling terrain and proximity to significant waterways. The region features a network of trails, including paved pathways and park routes, suitable for road cycling. Elevation changes are generally moderate, with routes often following river corridors or connecting urban green spaces.
Last updated: May 4, 2026
5.0
(4)
42
riders
44.9km
01:57
190m
190m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
11
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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5.0
(1)
18
riders
18.8km
00:48
50m
50m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
9
riders
21.0km
00:56
90m
90m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
8
riders
25.8km
01:12
120m
120m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Caledonia
The Pike River Pathway is a great paved, multiuse trail. It runs alongside the river with the same name. The path passes through a variety of landscapes, including meadows, fields and woods. It is a great place for a run completely free of car traffic.
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The Abandoned Ladish Sand Pit is often filled in with water and right off of the Oak Creek Trail. Oak Creek runs right behind it, making this spot a nice area to keep an eye out for birds and other wildlife.
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Grant Park Beach in Milwaukee is a sea glass lover's haven. Delight in the thrill of discovering coveted pieces as you sift through the sands. Enjoy the refreshing ocean breeze and the allure of crystal-clear waters.
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A beautiful path with expansive views of Lake Michigan. A perfect path to cycle on, on a still summers day.
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A great little pond to make a rest stop along your bike ride on the Oak Leaf trail There are usually people fishing on the shore to take a look at.
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The Abandoned Ladish Sand Pit is often filled in with water and right off of the Oak Creek Trail. Oak Creek runs right behind it, making this spot a nice area to keep an eye out for birds and other wildlife.
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Grant Park Drive runs along the coast but is separated from Grant Park Beach by a strip of woodland. There are some trails through the woods so you can access the beach from a number of different places, but the best option is to use the Oak Creak parking lot near Ferch's Beachside Grille. There are plenty of services here such as a playground and café, and you can walk right onto the beach.
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South Milwaukee Lagoon Pond is a popular fishing spot fed by Oak Creek (which flows out into Lake Michigan) along the Oak Creek Parkway in South Milwaukee, Wisconsin. This is a nice place to ride past as you explore the area.
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Road cycling routes in Caledonia, Wisconsin, are characterized by rolling terrain and proximity to significant waterways like the Root River. You'll find a network of paved pathways and park routes, with generally moderate elevation changes. Routes often follow river corridors or connect urban green spaces, offering varied scenery.
There are 15 road cycling routes available around Caledonia, Wisconsin, on komoot. These routes offer a range of experiences, from shorter, easy rides to longer, moderate options.
Yes, Caledonia offers plenty of options for beginners. Out of the 15 available routes, 12 are rated as easy. An example is the Oak Leaf Trail loop from Milwaukee County Sports Complex, which is 12.6 km long and takes about 32 minutes to complete.
For a longer ride, consider the Highland Memorial Park – Root River Parkway loop from Truck Parking. This moderate route spans 52.8 km and typically takes around 2 hours 22 minutes, following the scenic Root River Parkway.
Yes, the Grant Park Beach – Oak Leaf Trail — Shore line loop from Oak Creek is a popular choice. This 44.9 km easy route offers a blend of shoreline views and established trail sections, taking about 1 hour 57 minutes to complete.
Many routes in Caledonia incorporate parks and riverways. For instance, the Petrifying Spring County Park – Pike River Pathway loop from Mount Pleasant is a 32.9 km easy trail that leads through parklands and along the Pike River Pathway.
The road cycling routes around Caledonia are highly rated by the komoot community, with an average score of 5.0 stars from 5 reviews. Cyclists often praise the well-maintained paved pathways and the scenic beauty of the river corridors and park routes.
Yes, Caledonia is part of the Racine County Trail System, which includes connections to the Oak Leaf Trail and other Wisconsin State Trails. The Pike River Pathway, a paved multi-use trail, is also excellent for road biking, offering a car-traffic-free experience through meadows, fields, and woods.
While cycling, you can explore areas like the River Bend Nature Center, which offers nature trails. The region is also close to the Root River, providing opportunities for kayaking and fishing, and is just 15 miles west of the Mississippi River, offering scenic bluffs and vistas.
Yes, the road cycling network in Caledonia includes connections to larger trail systems like the Oak Leaf Trail. Routes such as the Oak Leaf Trail – Root River Parkway loop from Froemming Park integrate these connections, offering diverse riding experiences.
The duration of road cycling routes in Caledonia varies. Shorter, easy routes like the Oak Leaf Trail loop from Milwaukee County Sports Complex can be completed in about 32 minutes, while longer, moderate routes such as the Highland Memorial Park – Root River Parkway loop from Truck Parking can take over 2 hours.


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