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 58 trails covering 790 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 Buffalo Creek Trail makes a loop around the scenic Buffalo Creek Forest Preserve in Long Grove. The crushed-gravel trail provides access to facilities throughout the park. Along the way, you’ll...
The 53-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...
Prospect Heights has very few sidewalks, so biking, inline skating or walking are moved to the streets or in the parks. Don't underestimate the Prospect Heights Bike Path which is over four miles of...
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...
Ridgefield Trace currently consists of two short segments open for use. The western section runs from McHenry County College on US 14 in Crystal Lake to just west of N. Oak Street. Active railroad...
The Glacial River Trail provides bikers, pedestrians, and in-line skaters with a 55.8-mile off-road/on-road rural route winding through farmland, prairie, wetlands, and woodlands as it passes through...
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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...
Meadowbrook Trail parallels Meadowbrook Road offering a useful and convenient off-road route through northwest Waukesha. It begins at a connection to Lake Country Recreation Trail, a 15-mile east-west...
The Brown Deer Recreational Trail runs through the Village of Brown Deer, a suburb of Milwaukee. The tree-line route parallels an active rail line through commercial and residential areas. Mid-way,...
The Seven Waters Bike Trail is a scenic corridor stretching more than 17 miles northsouth between Burlington and Muskego Lake into Waukesha County. The trail was originally three trails, locally...
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....
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...
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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...
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Racine’s southeastern neighborhoods are home to the North Shore Trail, which extends south to the Racine–Kenosha county line. Because Racine County standardized its signs several years ago, you won't...
The North Shore Bike Path runs for nearly 8 miles between Lake Bluff and Mundelein, paralleling State Route 176 for the path's entire length. The trail is one of dozens in the Chicagoland area, all of...
If you’re going to visit the historical communities that lie just west of Lake Michigan, why not use the former route of the venerable interurban railroad? The Ozaukee Interurban Trail stretches the...
Although the Phyllis Harmon Path is short, it's an important connector in an east-west bike/ped route between Arlington Heights and Glencoe. Following Dundee Road, the paved trail goes from the Des...
The paved New Berlin Recreation Trail runs straight as an east–west compass bearing for 7 miles through the western Milwaukee suburbs, from New Berlin to Waukesha. While it is void of trestles,...
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...
The White River State Trail is composed of two separate segments: a 12-mile stretch that runs between Elkhorn and just west of Burlington in Walworth County, and a 7-mile section that connects the...
The Lake Country Recreation Trail runs from the western edge of Waukesha to Oconomowoc in Wisconsin’s Lake Country area. Most of the trail was built on a former Milwaukee-Watertown Interurban Railway...
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...
The Brown Deer Recreational Trail runs through the Village of Brown Deer, a suburb of Milwaukee. The tree-line route parallels an active rail line through commercial and residential areas. Mid-way,...
If you’re going to visit the historical communities that lie just west of Lake Michigan, why not use the former route of the venerable interurban railroad? The Ozaukee Interurban Trail stretches the...
The Duck Lake Nature Area Trail follows the southern side of Lake Como between Lake Geneva and Como, Wisconsin, not far from the Illinois state line. The trail is more rustic than most rail-trails and...
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 Robert McClory Bike Path runs the length of Lake County, knitting together a string of communities on the north shore of Chicago all the way to the Wisconsin border. In 1997, the trail was named...
Meadowbrook Trail parallels Meadowbrook Road offering a useful and convenient off-road route through northwest Waukesha. It begins at a connection to Lake Country Recreation Trail, a 15-mile east-west...
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...
Prospect Heights has very few sidewalks, so biking, inline skating or walking are moved to the streets or in the parks. Don't underestimate the Prospect Heights Bike Path which is over four miles of...
The Glacial River Trail provides bikers, pedestrians, and in-line skaters with a 55.8-mile off-road/on-road rural route winding through farmland, prairie, wetlands, and woodlands as it passes through...
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 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 Stone Mill Trail runs between Lawrence Road in Harvard and Maxon Road in Chemung. The 1.5-mile, paved trail mostly parallels County Highway 17 (Ramer Road) and active railroad tracks, and will...
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...
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 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...
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...
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 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 Duck Lake Nature Area Trail follows the southern side of Lake Como between Lake Geneva and Como, Wisconsin, not far from the Illinois state line. The trail is more rustic than most rail-trails and...
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 Glacial River Trail provides bikers, pedestrians, and in-line skaters with a 55.8-mile off-road/on-road rural route winding through farmland, prairie, wetlands, and woodlands as it passes through...
The East Northbrook Trail is a 1-mile route through a wooded corridor adjacent to an out-of-service rail corridor in the Village of Northbrook. The trail provides access to residential neighborhoods,...
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 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...
The Stone Mill Trail runs between Lawrence Road in Harvard and Maxon Road in Chemung. The 1.5-mile, paved trail mostly parallels County Highway 17 (Ramer Road) and active railroad tracks, and will...
The 13.5-mile Lake Michigan Pathway keeps you in close touch with the sixth-largest freshwater lake in the world as it links rail-trails north and south of the port city of Racine. Along the way, the...
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...
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...
Prospect Heights has very few sidewalks, so biking, inline skating or walking are moved to the streets or in the parks. Don't underestimate the Prospect Heights Bike Path which is over four miles of...
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 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 Buffalo Creek Trail makes a loop around the scenic Buffalo Creek Forest Preserve in Long Grove. The crushed-gravel trail provides access to facilities throughout the park. Along the way, you’ll...
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 North Shore Bike Path runs for nearly 8 miles between Lake Bluff and Mundelein, paralleling State Route 176 for the path's entire length. The trail is one of dozens in the Chicagoland area, all of...
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...
The Hebron Trail rolls across the northern Illinois prairie through the former corridor of the Kenosha and Rockford Railroad, known as the Kenosha Division Line at the time of its demise in 1939....
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 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...
This is all ripped up now, they are replacing the power lines. Still rideable but not relaxing
The areas around the trail especially in the three bridges park are quite bare currently.
I really wish that there were permanent "available/not locked" bathrooms along the trail itself besides at the urban ecology center and the seasonal port-o-potties during baseball season...Would be nice also if there was a light fixture on the bridge itself that is the exit of the three bridges park.
Otherwise this long trail that goes in different directions is pretty awesome. I've seen skunks and even frogs a few times last summer...
If you start in Algonquin I suggest parking in the park at the corner of Rt. 62 and Main St. I parked near the clock tower and had to ask a passing cyclist where to catch the trail. Once on the trail, the portion from Algonquin to Elgin is one of the best marked trails I've been on. It is very well maintained and passes through historic areas and scenic beauty. There were many walkers and joggers as well as cyclists. Also, there are plenty of quality rest areas along the way.
Have photographed 30 deer since walking from Dam No 4 Woods to Campground Road Woods, a nice relaxing walk to see squirrels, chipmunks, birds, rabbits and o yes the deer. This is a beautiful trail to walk and much safer than walking on the street or road. I live one mile from Dam No 4 Woods so it is easy for me to get there.
Set out on a gorgeous fall day and enjoyed the scenery, but not for very long. I had a road bike and spent most of the first six miles east from Elkhorn watching the trail surface. It was pretty well maintained but the 'concrete' only applies to the road crossings. The rest is somewhat crushed gravel. And then just past the coffee shop (about mile six) it gets sandy and very large gravel and I had to turn around. The good news is that the roads are excellent out here, so I rode back on those. Passed almost no other trail users and the tree canopy is lovely. Would like to ride this again but definitely suggest you take a hybrid bike!
I have walked this frequently and have had a lot of fun and excitement saw many deer and small animals chipmunks, squirrels and saw a couple of cardinals, I walk this once a day and have a good time met a lot of nice people while walking .
My husband and I decided to take up biking and this was our first trail ride and we really enjoyed it. I have a small dog and she travels in a pet basket and she also really enjoy the three hour ride. Mostly gravel but well maintained.
I ride this trail every chance I get as I train for a triathlon. I ride my road bike on this paved trail and ride the unpaved Illinois-Mich Canal trail on the mountain bike. I am retired and ride multiple times per week.
Negatives: Somewhat rough in sections so I keep tires ~50psi for a smoother ride. Some tricky sections till you get to know the trail.
Positives (too many to list all): Good pavement in most areas, repaving is continuously fixing bad spots. Nice water refill stations plus drinking fountains, washrooms & repair stations with tools and pumps. No need to risk riding with traffic. Nice small climbing hills for a sprint challenge. Well shaded with nice woods & great river views. Very little traffic on weekdays. Weekends are fun & not too crowded. Oswego to Crystal Lake gives a round trip century ride.
These trails are the best in our nation for long fitness rides without mixing with traffic. I feel guilty riding these near empty trails alone. Where is everybody? ;))
A great trail, very pretty even on the in-city parts riding through the woods. There's plenty of shade and the paved surface is great for my recumbent trike. The trail is well marked and drivers were super courteous about stopping when I needed to cross. I stopped and had a nice swim at Menomonee Park
I really like this trail and have ridden it now several times with both a road bike and a light hybrid. Pros: long, paved, scenic, uncrowded. Beautiful farmland and wildflowers, lots of trees for a shady ride on a hot day, wildlife and peaceful views. Stretches of the trail that are in great shape and a few key rest areas and comfort stations along the route. Excellent diner (Boone Co. Family Restaurant) right off the trail in Caledonia. Nicest long section is west of Caledonia. Cons: many parts of this trail are bad to downright treacherous, especially near bridges. You could easily catch your tire in a center crack while trying to avoid a pothole on your side of the trail. No mile or distance markers. Shady trail means debris is damp after a rain, and sketchy for road bikes. Some horrible bridge transitions. Trail is out east of Capron at the moment. Recommendations: Could be fabulous if better maintained. In current condition, better for a hybrid. OK for a road bike on a dry day. Either way, wear a helmet.
First let me start by saying the Oak Leaf trail is an excellent trail that circles Milwaukee county. I have been using this trail ever since it use to be called the '76' trail. Unfortunately, I haven't been on the south end in years. I recently decided to go south(starting at Greenfield park) with the intent to get to the newer of Milwaukee Counties parks, Bender park. When I got to Drexel at which point I would normally go straight east toward Grant Park I found I was able to continue South. Not having checked the trail map prior to my adventure I made the assumption that the ability to go further South of Drexel would somehow meander its way to Bender park. Unfortunately I was mistaken. Needless to say I managed to get to Bender park by going East on Ryan Rd./Hwy 100. I eventually got back on the Oak Leaf trail down near Grant park after heading North from Bender park through South Milwaukee on 5th Ave. Let me once again reiterate how awesome the Oak leaf trail is and how I should have checked the map prior to my excursion. As an avid biker I can only hope that at some point there will be an extension/offshoot of the Oak leaf trail that will allow bikers to safely get to that corner of Milwaukee county via trails.
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