Explore the best rated trails in Caledonia, WI. Whether you're looking for an easy walking trail or a bike trail like the Eisenbahn State Trail and New Berlin Recreation Trail. With more than 66 trails covering 825 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
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The 2.3-mile multiuse trail wraps around Lake Andrea in Pleasant Springs Park. The trail is an easy walk, run or ride around the lake, and is accessible for a wide range of users. It also helps users...
The Pike River Pathway is a paved, multi-use trail that runs along both sides of the reconstructed Pike River through the Village of Mount Pleasant and unincorporated parts of Racine County. The path...
The Racine-Sturtevant Trail runs for 3.5 miles from the western side of Racine to near the eastern edge of the Village of Sturtevant. The trail occupies an abandoned rail corridor for most of its...
The 9-mile Green Bay Trail runs parallel to Chicago's Metra commuter rail line north of the Chicago city limits. Stretching through North Shore towns such as Kenilworth, Winnetka, Highland Park and...
The Cushing Park Road Recreational Trail begins on the western outskirts of Delafield, a small community about 30 miles west of Milwaukee. From Delafield's Main Street, the trail heads south,...
The Paul Douglas and Crabtree Preserve Trail System connects two large nature preserves in northwestern Cook County. The trail begins at the Old Stover Trailhead in the Crabtree Preserve, near the...
The Des Plaines River Trail runs alongside the Des Plaines River for just over 56 miles, protecting watershed habitat and forestland through much of Lake and Cook Counties. The trail is a natural...
With farmland to the east and the Des Plaines River Floodplain to the west, this picturesque trail is a relaxing adventure on two feet or on wheels. The crushed stone trail runs from Prairie Springs...
The Ridgefield Trace is a multi-use pathway that runs through suburban Crystal Lake, Illinois. The trail takes its name from the original Indian trace that once ran along the route of what is now...
About an hour northwest of Chicago, the beautiful Grant Woods Forest Preserve spans more than 1,000 acres, offering an outdoor respite of prairie, woodlands and marshes. The crushed limestone pathway...
The Root River Pathway uses a combination of off-road trail and on-road route to form a crescent around the City of Racine. The trail closely follows the bends of the Root River, making it a great...
The Deer Grove Trail is one of several great Chicagoland trails located in properties of the Forest Preserve of Cook County. Deer Grove is the oldest of all the Cook County preserves. It's comprised...
The Millennium Trail currently spans just over 30 miles in two disconnected segments, but there are plans to extend it to 35 miles and connect it to the Des Plaines River Trail. The trail goes through...
Kinnickinnic River Trail (called the KK River Trail by locals) runs just over 2 miles in southern Milwaukee, following the river through a densely populated and industrial corridor. The trail links...
The Prairie Crossing Bike Path is a hard surface trail connecting Mundelein to Grayslake in central Lake County, Illinois. The trail is perpendicular to the 30-plus-mile Millennium Trail, which it...
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An excellent example of land use in greater Chicago, the entire Skokie Valley Trail corridor is a rail-with-trail, paralleled by double tracks that sit about 40 feet to the west of the trail surface....
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The Fox River Trail runs diagonally along its namesake waterway through Waukesha in southeastern Wisconsin (just outside of Milwaukee). A trailhead at the E.B. Shurts Environmental Education Center in...
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The Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail-trail spans just over 26 miles from the Wisconsin border and the farms and...
Racine County's eastern edge is home to the MRK Trail, a rail-with-trail that extends north from the City of Racine to the Village of Caledonia. Because Racine County standardized its signs several...
The Lake Geneva Bike Path runs through the scenic resort city, offering connections to many of the community’s amenities. The trail has five unique, color-coded segments. The Blue Route is the...
The Ridgefield Trace is a multi-use pathway that runs through suburban Crystal Lake, Illinois. The trail takes its name from the original Indian trace that once ran along the route of what is now...
Helping to extend the excellent network of trails around the city of Racine deeper west into the heart of the county, the Racine County Bike Trail serves as a disconnected addition to the...
The Racine-Sturtevant Trail runs for 3.5 miles from the western side of Racine to near the eastern edge of the Village of Sturtevant. The trail occupies an abandoned rail corridor for most of its...
The village of Palatine has connected many of its community assets with two long sections of off-road, multi-use trail. The more popular northern section is the one most references call simply and...
Broad blue skies strung with white cloud wisps; gem-green fields harboring cattails and butterflies; canopied glens giving way to cavernous quarries. It's all part of the ride on the Bugline...
About an hour northwest of Chicago, the beautiful Grant Woods Forest Preserve spans more than 1,000 acres, offering an outdoor respite of prairie, woodlands and marshes. The crushed limestone pathway...
The Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail-trail spans just over 26 miles from the Wisconsin border and the farms and...
The Techny Trail links downtown Glenview, a charming village northwest of Chicago, with the Techny Basin, a scenic wetlands area adjacent to the West Fork of the Chicago River's North Branch....
The North Branch Trail follows the North Branch of the Chicago River over 20 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...
With farmland to the east and the Des Plaines River Floodplain to the west, this picturesque trail is a relaxing adventure on two feet or on wheels. The crushed stone trail runs from Prairie Springs...
The 52-mile Glacial Drumlin State Trail between Cottage Grove and Waukesha provides a glimpse into the past when glaciers bore down on southeastern Wisconsin in the last Ice Age. Those gigantic sheets...
The Muskego Recreation Trail follows a corridor originally used by the Milwaukee Electric Railway & Light, an interurban railroad in southeastern Wisconsin. The corridor was later acquired by...
The Pelishek-Tiffany Nature Trail runs for 6 miles along an abandoned railroad corridor, between the towns of Allens Grove and Clinton. The trail is open to snowmobiles, cyclists, horseback riders and...
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 125 miles in and around the city of Milwaukee on a changing terrain of flat...
The WE Energies Trail, so named because it uses a Wisconsin Energy Corporation utility corridor for much of its route, links Racine and Oak Creek in Racine and Milwaukee counties. Despite the presence...
In 1957, baseball legend Hank “The Hammer” Aaron led the Milwaukee Braves to the first of two consecutive World Series appearances and a championship over the usually dominant New York Yankees. In...
The KR Trail is a new addition to Kenosha County’s growing bike-ped network. The trail picks up where the Kenosha County Bike Trail leaves off, in Petrifying Springs Park. From the northwest corner of...
The Middlefork Savanna Forest Preserve is a natural gem hidden in an high-income neighborhood of Lake Forest, Illinois. Those 600 acres are home to perhaps the best-preserved example of the rare...
Helping to forge a connection between the northern and southern segments of the Kenosha County Bike Trail, the Kenosha Pike Bike Trail also has plenty to offer in its own right, giving trail users a...
The Milwaukee RiverWalk provides a pleasant way to get around Milwaukee from the Historic Third Ward, through downtown, and north to the Lower East Side. It also has easy connections to three other...
The North Branch Trail follows the North Branch of the Chicago River over 20 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...
The Techny Trail links downtown Glenview, a charming village northwest of Chicago, with the Techny Basin, a scenic wetlands area adjacent to the West Fork of the Chicago River's North Branch....
With farmland to the east and the Des Plaines River Floodplain to the west, this picturesque trail is a relaxing adventure on two feet or on wheels. The crushed stone trail runs from Prairie Springs...
The WE Energies Trail, so named because it uses a Wisconsin Energy Corporation utility corridor for much of its route, links Racine and Oak Creek in Racine and Milwaukee counties. Despite the presence...
This bike path sits on the east side of Almond Road between Washington Street and Fairfield Lane in Gurnee. The 8-foot wide asphalt path is used by residents as a spot for exercise and recreation, but...
The 2.3-mile multiuse trail wraps around Lake Andrea in Pleasant Springs Park. The trail is an easy walk, run or ride around the lake, and is accessible for a wide range of users. It also helps users...
Although short, the West Allis Cross Town Connector represents an important start to a future link between three trails in Milwaukee County. Currently, the trail begins at a junction with the New...
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for more than 125 miles in and around the city of Milwaukee on a changing terrain of flat...
The Long Prairie Trail journeys across the width of agricultural Boone County for nearly 14 miles on the railroad corridor previously used by the Kenosha and Rockford Railroad, later known as the...
The Prairie Trail runs the length of McHenry County and is managed by the McHenry County Conservation District. The rail-trail spans just over 26 miles from the Wisconsin border and the farms and...
The Ridgefield Trace is a multi-use pathway that runs through suburban Crystal Lake, Illinois. The trail takes its name from the original Indian trace that once ran along the route of what is now...
The Chain O' Lakes Bike Path is a paved trail that runs between E. Grand Avenue in Fox Lake and Grant Woods Forest Preserve to the east. The trail parallels the railroad track and Rollins Road/CR 31,...
The Root River Pathway uses a combination of off-road trail and on-road route to form a crescent around the City of Racine. The trail closely follows the bends of the Root River, making it a great...
The Millennium Trail currently spans just over 30 miles in two disconnected segments, but there are plans to extend it to 35 miles and connect it to the Des Plaines River Trail. The trail goes through...
Helping to forge a connection between the northern and southern segments of the Kenosha County Bike Trail, the Kenosha Pike Bike Trail also has plenty to offer in its own right, giving trail users a...
The village of Palatine has connected many of its community assets with two long sections of off-road, multi-use trail. The more popular northern section is the one most references call simply and...
The Paul Douglas and Crabtree Preserve Trail System connects two large nature preserves in northwestern Cook County. The trail begins at the Old Stover Trailhead in the Crabtree Preserve, near the...
The Kenosha County Bike Trail is open in two sections separated by dense neighborhoods in the City of Kenosha. The northern segment runs northeast from 35th Street in the city to 1st Street at the...
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The the Fox River Trail (FRT) was built on stretches of three former railroads: Chicago, Aurora & Elgin; Aurora, Elgin, & Fox River Electric; and Chicago & North Western. Today, it hosts a multitude...
Kinnickinnic River Trail (called the KK River Trail by locals) runs just over 2 miles in southern Milwaukee, following the river through a densely populated and industrial corridor. The trail links...
We began our adventure, August 31, 2021, at Whispering Oaks Park in McHenry, IL and set off going north. Almost immediately we crossed busy W. Elm St./Rte 120, but quickly left traffic behind as we passed McCullom Lake and East Beach Park and began passing farm fields and then the Glacial Park Conservation Area, full of beautifully blooming late summer prairie plants. Continuing north we passed through the small town of Ringwood and then into Richmond, IL where we negotiated another busy road crossing at Kenosha St/Rte 173 and then on into the North Branch Conservation Area where the Hebron Trail connects to the Prairie Trail, and just shy of the Wisconsin state line. The North Branch Conservation Area is a lovely, restored prairie area with rolling hills and a destination in it's own right. Storm clouds began to gather, and we turned around and headed back south. We stopped for some light refreshment at the Rusty Nail Saloon's outdoor patio, right on the trail, and also noted a good spot for ice cream, milk shakes, etc. just across a large parking lot to the west of the Saloon. This trail has a lovely mix of town and country and this section of the trail was easy riding with good path conditions and minimal road crossings to negotiate. We are hoping to get back again in Summer 2022.
Came from Chicago. The trail head near Harvard was locked up upon arrival had to park on a street in the town over (capron) too get on. Overall pretty cool, nice n flat and nice Midwest middle of nowhere scenery. Trail has some bumps and cracks from time and is partially crushed compacted gravel but very leisurely.
I have been driving past the perimeters of this preserve for years! FINALLY went in and loved it…. Nice hills, bridges, small lakes, and a large prairie. I highly recommend!
You can make about a 5 mile loop out of the trail by using some of the connected trails. Takes you through some wooded areas and has some smooth gravel areas as well. I liked that it had some small hills to make it a bit more challenging.
Very short trail, it does connect to the big bend muskego trail
We started this trail out at merton firemans park, and went east to the falls, trail is all paved, beautiful scenery, goes under 164, nice woods, great view of the quarry, great ride
Was very excited to try this trail between Fish Hatchery (Delafield) and Oconomowoc downtown....but was disappointed. So much of the trail is between power line poles and fairly uninteresting. The worst, however, was the stretch around Nemahbin Lake--where the trail literally disappears completely and you are left navigating a narrow, heavily travelled road with no shoulders in some places! I can't believe this portion is still called the Lake Country trail--when there is no trail. I would not recommend this route for families with young children, given this dangerous stretch with cars whizzing past.
...loved the concept of this path and the ability to enjoy downtown Delafield and downtown Oconomowoc, though. I just wish is was better developed and a bit more interesting/rustic.
I think the Kinnickinnic River Trail is a good riding trail. You can see lots of nature on the lower portion of the trail (south of Lincoln Ave). The upper portion runs along the railroad tracks which is separated by a chain link fence for safety reasons. Amtrak rolls by about every few hours. The day I rode it (Sunday afternoon in early Oct), the trail wasn't very busy. Probably due to Sunday afternoon football games.
The only bad part of the trail is that you have to ride the road for 0.7 miles to get to the lower portion. The good part about the road is that it isn't very busy and it does have bike lanes.
It’s right in our backyard and we have been on every portion with e bikes. LOVE it all. See wildlife every time. Also hike in winter months
This trail is so bumpy I would not classify it as a bike trail.
Explored this trail, and it’s really good with lot of forest area and greenery. The paved road through the entire ride is a big plus for the trail. And the loop is a plus as well. We don’t feel like going straight and getting back.
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