Find the top rated bike trails in Pleasant Prairie, whether you're looking for an easy short bike trail or a long bike trail, you'll find what you're looking for. Click on a bike trail below to find trail descriptions, trail maps, photos, and reviews.
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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 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 North Shore Channel Trail extends from the junction of Green Bay Road and McCormick Boulevard in northern Evanston to the junction of Lawrence Avenue and Francisco Avenue in Chicago. All but 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...
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 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 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...
The Timber Ridge trail is located on the eastern side of the Timber Ridge Forest Preserve in west Chicago. The preserve offers several trails, fishing, picnicking, and is home to Kline Creek Farms,...
The North Branch Riverwalk is a 0.6 mile biking and walking trail located on Chicago's northside along the North Branch of the Chicago River, nestled between Gordon Tech High School and Lane Tech High...
The Union Pacific Recreation Path offers a short route through the Village of Lincolnwood's east side between Devon and Touhy avenues. Following the former Union Pacific Railroad, the rail-trail...
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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 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 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 Poplar Creek Trail is a 9.5-mile paved loop around Poplar Creek Forest Preserve near Hoffman Estates. The trail has a couple of hills but is otherwise level and makes for a pleasant journey...
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 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...
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The western segment of the Great Western Trail in Illinois follows 17 miles of a former railway corridor through DeKalb and Kane counties, between LeRoy Oakes Forest Preserve and the town of Sycamore....
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The Salt Creek Trail travels nearly 27 miles from the Brookfield Zoo to Busse Woods Forest Preserve. Along the way it connects several beautiful county forest preserves and other woodland...
The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. It consists of five connected trail segments with three main branches that converge at Volunteer Park (West...
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 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 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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The 4.4-mile River Bend Trail is so named for the loop of Fox River along which it follows on its eastern end. It's here that you can connect to the scenic Fox River Trail to travel 43 miles along 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 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...
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...
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 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...
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...
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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...
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...
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 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...
Prospect Heights Bike Path runs between Woodland Trails Park and Country Garden Park, paralleling the commuter rail tracks on its north–south leg. The trail provides a nice off-road route through 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...
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 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 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 Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago and passing many cultural and tourist attractions throughout the...
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...
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The Skokie Valley Trail in Cook County parallels active train tracks in the Village of Skokie, providing easy access to both the Oakton–Skokie and Dempster–Skokie stations on the CTA’s Yellow Line....
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 4.4-mile River Bend Trail is so named for the loop of Fox River along which it follows on its eastern end. It's here that you can connect to the scenic Fox River Trail to travel 43 miles along the...
The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago and passing many cultural and tourist attractions throughout the...
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...
The Union Pacific Recreation Path offers a short route through the Village of Lincolnwood's east side between Devon and Touhy avenues. Following the former Union Pacific Railroad, the rail-trail...
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 Pike River Pathway is a short trail on both sides of the reconstructed Pike River in the Village of Mount Pleasant. The path is convenient to several neighborhoods in the community. Birds, frogs...
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 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...
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...
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 Poplar Creek Trail is a 9.5-mile paved loop around Poplar Creek Forest Preserve near Hoffman Estates. The trail has a couple of hills but is otherwise level and makes for a pleasant journey...
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 H.U.M. Trail (a.k.a. the Huntley-Union-Marengo Trail) was planned to link all three of its namesake northern Illinois towns, but so far only connects Marengo and Union. Interestingly, the...
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 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 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 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...
Honey Creek Pkwy is a very pleasant windy smooth road. Although you do have to go across Wisconsin Ave and Bluemound road which can be quite busy streets.
We picked up the Oak Leaf branch opposite 72nd st that goes through Wauwatosa. Once we got on the trail there were a lot of people and kids walking in large groups. A few bikers too. Good thing the trail is wide as you go past Hart and Hoyt parks.
We made a left on Swan Blvd. Quite a busy street with fast traffic but luckily you're not on it very long. Right after you pass under the railroad bridge you make a right onto Underwood Pkwy. Very bumpy road but lightly traveled
Trail was closed where it passes under Hwy 100/Mayfair Road but detour was clearly marked. Detour had you cross Waterplank road then wind through the industrial park which was deserted on Saturday afternoon until routing you to cross Hwy 100 on Research Drive. Even though we pushed the button we never did get a walk light across Hwy 100.
We met up again with the Oak Leaf trail which was pleasant then took the Hank Aaron trail back east.
Love the length of this. Usually do it in a little over an hour, and at just under 20 Miles this is a perfect ride to help you maintain and work on a faster pace when training for those much longer rides. Surface is good enough, not the best but not even close to being bad. Good straight aways, only a few roadway crossings on the entire path so you can maintain a good speed without having to stop or slow down.
We decided to bike this trail because it was going to be in the 90s (Fahrenheit) today and we figured it would be mostly shaded. It was mostly shaded with a lot of greenery and a creek that wound back and forth along most of the trail. There were some clouds of bugs but they didn't bite. Many areas of the trail had been filled in with loose fill but the rest of the trail was firm and dry as the weather has been quite hot lately. There is a very clean porta potty near the bike rental place. I'd like to bike the other leg of the trail to Kansasville someday.
This trail was perfect. I took my rollerblades with me while on vacation and skated here. It was very cool. The architecture is amazing for admiring and along a beach with things going on in the lake made for great scenery in all directions. Even took an intermission to get my feet in the sand since the trail goes on the beach. I will definitely be back on this trail next time I'm in Chicago!
Won’t be riding this again on the road bike. Fumes from roads make this not so pleasant. Sculptures and play ground for kids are great but that’s about it. Got lost when it flips to other side of river. This route is for kids on bikes, not serious cyclists. Fun all the same with the kids for sure
Coming from the uk I was pessimistic about city cycling. After getting bored of the lake front trail and north Sheridan/Green Bay road repeats this trail is a god send. Love it. Perfect for road biking and quiet(midweek) will continue to look for other trails but this one will be hard to beat.
A friend and I rode sections of the Oak Leaf trail as part of a multi-day trip from Chicago to Cedarburg, WI. We rode 10 different trails and found some sections of the Oak Leaf trail to be as good as it gets! It is paved and well maintained and generally runs through quiet country and/or neighborhoods. We only had a couple of issues - one being that part of the trail was closed and the detour signs were not clear for people from out of state. We are very thankful for friendly "natives" who helped us find our way to where the trail was open. The second was a section near Oak Creek that had 4 small sections with significant flooding - about 18 inches of water. It is kind of fun riding through big puddles, but unfortunately, the water was deep enough to soak the bottom of our saddlebags. Nonetheless, we thoroughly enjoyed riding on this trail (the sections of the trail we did ride) and would recommend it highly! We found very few other riders/users - but I am guessing that rain, wind and cloudy days keep locals indoors--because the trail itself is wonderful!
This little trail provides a smooth connection between the Oak Leaf Trail and the Ozaukee Interurban trail. It is very nice with a good, smooth surface - riding through Browndeer neighborhoods. One can ride miles and miles in Wisconsin without riding on a road!
On a recent trip riding trails from Chicago to Cedarburg, WI, we found this trail to be one of the best of the 10 trails we rode during our 6 day trip. It does cross streets, and drivers generally don't stop (although we thought pedestrians had the right of way in Wisconsin - the average driver doesn't seem to know that!). But the trail is in such great condition and generally goes through quiet fields and neighborhoods. We thoroughly enjoyed it especially after some very sluggish days on wet crushed limestone. We kept thinking how lucky all the people who live near that trail are and in fact, of all the trails we rode, this one had the most other trail riders/walkers/runners!
Excerpted from my blog (https://desplainesrivertrailcycling.blogspot.com/)
April 12, 2018
First ride of 2018, 42 miles down and only 1,958 to hit my annual target! The afternoon started out warm and sunny, a rare occurrence this Spring as the start of April hasn't been this cold in Chicago in 137 years with multiple snow storms! About 90 minutes into my ride the wind shifted and it was like someone turned on an air conditioner - in five minutes the temp went from high 60's to 50 degrees which is where I usually draw the line on riding 'cause it gets too cold for me.
Overall trail conditions are pretty decent with no flooding from Deerfield Road up to Independence Grove and while the trail surface is somewhat rutted from the long winter it is in reasonably good shape. One word of caution, bring plenty of water as none of the wells along the trail are open for the season and are wrapped in plastic film.
I did the circuit around Independence Grove and from a distance spotted what appeared to be two baby owls peeking out of the hole in tree. I thought it was my lucky day and quickly snapped this pic (see on blog) only to get closer and realize they were fake, the dead giveaway is the yellow glue on their feet - fake news indeed :-)
Not much in the way of color on the trail yet, it has been too cold for any spring flowers.
This is the perfect trail in so many ways. Quieter, with water and restrooms, all sorts of native birds and animals, places to picnic and just enjoy the great outdoors. I feel lucky to have this trail just a couple blocks from my home on the south end. Summer here we come !
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