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 62 trails covering 813 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.
The Beerline Trail, so named because the corridor was once used by freight trains transporting the ingredients for beer to some of Milwaukee’s famous breweries, has contributed to the revitalization...
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 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...
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...
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 City of Franklin Hike and Bike Trail follows a corridor originally used by the Milwaukee Electric Railway & Light, an interurban railroad in southeastern Wisconsin. The corridor was later acquired...
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 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 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 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 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...
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...
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 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...
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 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...
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 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 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...
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...
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...
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 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...
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 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...
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 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 Bull Valley Road Shared-Use Path travels along the south side of Bull Valley Road in the city of McHenry, Illinois. The paved path is suitable for non-motorized uses including walking, jogging,...
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 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 City of Franklin Hike and Bike Trail follows a corridor originally used by the Milwaukee Electric Railway & Light, an interurban railroad in southeastern Wisconsin. The corridor was later acquired...
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 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 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...
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...
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 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 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...
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 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 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 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,...
Moraine Hills State Park Trail offers a wonderful experience for any geology or nature aficionado. A moraine is an accumulation of earth and stones carried and finally deposited by a glacier....
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 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 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 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 Bull Valley Road Shared-Use Path travels along the south side of Bull Valley Road in the city of McHenry, Illinois. The paved path is suitable for non-motorized uses including walking, jogging,...
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 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 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 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 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...
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...
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 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 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...
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 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...
I agree with the reviews of the trail south of Lake Cook Rd. It’s ok for a few miles south but there’s a notable difference of trail conditions from the trail north. Two different counties and budgets to maintain them, I assume. Traveled this trail multiple times this past COVID season. It’s my first year biking in 40 yrs and wow, what a great trail.
well-maintained paved trail with beautiful sceneries. Always enjoying to ride.
Started at Fairfield and 176 (waconda). Ample parking but not that crowded. Went north past the dog park through some gentle turns and inclines. Beautiful ponds along the way with plenty of benches along the way to stop and rest Went all the way to Ray’s and looped back around with a total of about 8-9 miles It is our go to trail for fresh air They also have a two other trails there, one goes northwest and one that goes east toward Mundelein
I parked just north of Golf at 294 right over the train tracks. Took the trail north and I loved it. The tracks do separate the trail and I’m surprised it’s not connected. The people who make and maintain these trails are national heroes. The dirt road north is perfect for mountain bikes. I rode about 7 miles to highway 68 I think it is. Awesome.
My first ride on this beautiful trail from Menomonee Park to Merton & back today on my recumbent trike. It is paved and mostly in the trees. I enjoyed the ride. 11-21-2020
I went on a walk/roll with my husband on this beautiful trail. The Fall colors were enchanting. He was able to get my wheelchair through the path without a problem. I love the wooded pathway and all of the beautiful trees and scenery.
I like the north branch of the trail for its beauty and the south branch for the rough ride and challenges. (Some nice scenery on the south branch too.) I have a 29er mountain bike. When I rode the south branch on my hybrid the first time I took that trail I had to take the bike in for repair afterwards. But on a mountain bike the south branch is a blast. Where else in the suburbs can you get a ride like that?
We just moved to Lindenhurst at the very beginning of the trail. I have many parts of the trail out of Volo when we stayed at Fish Lake Beach in our motorhome. I am a senior rider. The trail had lots of wildlife and lots of wildflowers.
Road with my son last Saturday from St. Charles to Richmond, IL. Spent the night at the Baymont Inn in Richmond, nothing fancy but friendly staff and clean. Surprisingly lively Saturday Night crowd in Richmond, had a good time grabbing dinner and having a night cap at a sidewalk table. The walk into town is not a stroll but fine on a nice evening. There is a wine/cheese place with a restaurant within a five minute walk from the hotel where we got a takeout breakfast. The Fox River Trail was good with some rough spots in South Elgin. Looks they may be re-routing the trail further from the river towards some new housing. Not a big deal but we were surprised at the trail conditions on that short stretch.
The Prairie Trail was fine for the most part. There was some construction in Crystal Lake and Algonquin that was a little unpleasant but again not that big a deal. The hills in Stern's Woods are short and steep and not typical for the trails in the area. Don't let this stop you from making the trip. We cruised right through with a little huffing and puffing. It did look like a southbound ride would offer a few more uphills. This was our first time north of Crystal Lake and we both enjoyed the ride, would do it again.
Beautiful tree canopies. Trail mostly grass, but biking it was no problem. Very little use, only encountered 4 other people & they were walking. Parking lot at Clinton, but only street in parking at Allen-Grove.
I LOVE the Des Plaines River Trail. But. Going north and going south are totally different experiences.
I live in Glenview, so I join the trail through an unmarked path I somehow found at the end of Carol Lane in the Timber Trails neighborhood just west of Milwaukee. I catch the trail in the East Lake woods.
If I go north, it's beautiful. There are weird spots. In Northbrook, you have to cross a busy Milwaukee Avenue (by Allgauers restaurant) with no stoplight. Then you have to ride up a little street to find the trail again. (There's an interesting story about how the Rat Pack played at the restaurant that used to be at the site of Allgauers, but we'll save that for another review.)
The woods are lovely. There's a Nature Center (not open during COVID). It feels like you've left civilization behind. Until you have to cross Dundee Avenue, which can be a bit nerve-wracking.
But there's a big meadow that I love. The trail is just a small rut at that point, but the meadow is thick and beautiful and serene. The last time I went through it, was the last time I felt totally at peace.
And the other reviewers are right. The difference between the Cook County Trail and the Lake County Trail are night and day. I'm surprised you don't hear and audible "POP" when you cross the bridge at Lake-Cook Road.
The Cook County side, while gorgeous, is dirt and mud, if it has rained, and roots to watch out for. The Lake County side is crushed gravel, wide trails and benches every other mile. I've only been five miles into the Lake County side, but that was enough to see herons resting in tree branches while I pedaled over a small, charming bridge.
And yet, while the Cook County side seems to be the embodiment of forest preserve patronage, (I got a nephew who's got a cousin who's got a friend who keeps the trails maintained) I still love it.
Which brings me to going south on the trail.
When I take people on the trail, I bring them south first because it's just so...different. And maybe not right if you just want an easy, lovely ride.
It's beautiful from Euclid past Central. Tall trees, with sparse underbrush give way to dense thickets that feel like the English countryside.
And then, yep, you get to the freight train tracks. You have to pick up your bike and carry it across the tracks. Freight trains are infrequent, but they come. Apparently there are plans to build a bridge. But until then, it's part of the adventure.
That soon leads into my favorite part of the whole trail. Riding through, or beneath, actually, downtown Des Plaines.
The path is paved and takes you right along the river, down below the street and commercial buildings. Pass through a tunnel, under a railroad bridge, and you soon come upon the Methodist Camp. A strange old series of buildings that have been around for more than 100 years. Before that, the Union Army used to train soldiers at the site.
Once you are past that, well, it depends how wet it's been. The trail can get flooded and super muddy, so be prepared to call it a day. And if that's the case, the tunnels that were built to go under Touhy and Devon and Lawrence can also get muddy and flooded, so you may have to cross those streets without a stoplight.
Irving Park is the same way and it, like the others, is a four-lane road at that point.
At this point, it's pretty. It's nature. But it feels pretty urban. The trail's a little bumpy too (I think they might have paved it a long time ago, and then didn't bother to keep it up. (Thanks, nephew's cousin's friend).
You even take a bridge over the Kennedy Expressway at one point.
I'm glad I finally made it all the way out to the trail's end at North Avenue. But it can get a touch dicey between Devon and Fullerton at times. That segment feels a little forgotten somehow. I hear there are plans to improve this section, and it would be a good thing.
In the end, North is beauty. South is adventure.
Happy trails!
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TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!