Pleasant Prairie, WI Cross Country Skiing Trails and Maps

1322 Reviews

Looking for the best Cross Country Skiing trails around Pleasant Prairie?

Find the top rated cross country skiing trails in Pleasant Prairie, whether you're looking for an easy short cross country skiing trail or a long cross country skiing trail, you'll find what you're looking for. Click on a cross country skiing trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
46 Results
Activities
Length
Surfaces
Type

Busse Woods Trail

11.6 mi
State: IL
Asphalt, Concrete

Deer Grove Trail

3.9 mi
State: IL
Asphalt

Des Plaines River Trail

56.1 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

DuPage River Trail

49.3 mi
State: IL
Asphalt

Fox River Trail (IL)

45.7 mi
State: IL
Asphalt, Concrete, Crushed Stone

Glacial Drumlin State Trail

53.2 mi
State: WI
Asphalt, Crushed Stone, Gravel

Grant Woods Bike Path

5.9 mi
State: IL
Crushed Stone

Great Western Trail (DeKalb, Kane)

18 mi
State: IL
Asphalt, Crushed Stone

Great Western Trail (DuPage)

12.7 mi
State: IL
Crushed Stone

H.U.M. Trail

3.5 mi
State: IL
Asphalt

Illinois Prairie Path

58.52 mi
State: IL
Asphalt, Concrete, Crushed Stone

Kenosha County Bike Trail

7.9 mi
State: WI
Asphalt

Millennium Trail (IL)

30.7 mi
State: IL
Asphalt, Concrete, Crushed Stone

Moraine Hills State Park Trail

11.4 mi
State: IL
Asphalt, Crushed Stone

New Berlin Recreation Trail

7 mi
State: WI
Asphalt

North Branch Trail

25.5 mi
State: IL
Asphalt

North Shore Trail (WI)

3 mi
State: WI
Asphalt

Oak Leaf Trail

123.6 mi
State: WI
Asphalt

Ozaukee Interurban Trail

30.1 mi
State: WI
Asphalt
Accordion

Palatine Trail

9.6 mi
State: IL
Asphalt, Concrete

Prairie Trail (IL)

26.4 mi
State: IL
Asphalt, Crushed Stone, Dirt, Gravel

Valley Line Trail

1.1 mi
State: IL
Asphalt

West Allis Cross Town Connector

0.9 mi
State: WI
Asphalt

West Branch DuPage River Trail

26 mi
State: IL
Gravel

White River State Trail

19.7 mi
State: WI
Concrete, Crushed Stone, Gravel

Beerline Trail

3.7 mi
State: WI
Asphalt

Buffalo Creek Trail (IL)

5.5 mi
State: IL
Crushed Stone, Gravel

Chain O' Lakes Bike Path

3.2 mi
State: IL
Asphalt

Green Bay Trail

6.5 mi
State: IL
Asphalt, Concrete, Crushed Stone

Lake Michigan Pathway

14 mi
State: WI
Asphalt, Concrete, Crushed Stone

Long Prairie Trail

13.9 mi
State: IL
Asphalt, Crushed Stone

MRK Trail

4.6 mi
State: WI
Crushed Stone

Muskego Recreation Trail

7.5 mi
State: WI
Crushed Stone, Dirt, Gravel

North Shore Bike Path

7.7 mi
State: IL
Asphalt, Crushed Stone

Pelishek-Tiffany Nature Trail

6 mi
State: WI
Dirt, Grass

Prairie Farms Trail

1.8 mi
State: WI
Crushed Stone, Dirt

Racine-Sturtevant Trail

3.5 mi
State: WI
Asphalt

Robert McClory Bike Path

25.4 mi
State: IL
Asphalt, Concrete, Crushed Stone

Seven Waters Bike Trail

18.6 mi
State: WI
Asphalt, Crushed Stone, Gravel

Stone Mill Trail

1.5 mi
State: IL
Asphalt

Techny Trail

3 mi
State: IL
Asphalt, Concrete

East Northbrook Trail

1.1 mi
State: IL
Asphalt

Prospect Heights Bike Path

4.2 mi
State: IL
Asphalt

Lake Geneva Bike Path

8.9 mi
State: WI
Asphalt
Trail Image Trail Name States Length Surface Rating
The Busse Woods Trail spans the Ned Brown Forest Preserve, a 3,700-acre natural space in the northwestern suburbs of Chicago. The preserve—popularly just called Busse Woods—has a large meandrous lake...
IL 11.6 mi Asphalt, Concrete
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...
WI 1.5 mi Asphalt
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...
IL 3.9 mi Asphalt
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...
IL 56.1 mi Asphalt, Crushed Stone, Dirt, Gravel
The DuPage River Trail spans 49.3 miles across two counties: DuPage and Will. The trail is open in several disconnected segments mainly in parks and forest preserves beginning in Bartlett and...
IL 49.3 mi Asphalt
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 of...
IL 45.7 mi Asphalt, Concrete, Crushed Stone
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...
WI 53.2 mi Asphalt, Crushed Stone, Gravel
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...
IL 5.9 mi Crushed Stone
The western segment of the Great Western Trail in Illinois follows 18 miles of a former railway corridor through DeKalb and Kane counties, between Sycamore Forest Preserve in the City of Sycamore and...
IL 18 mi Asphalt, Crushed Stone
The eastern segment of the Great Western Trail in Illinois follows almost 13 miles of an abandoned railway corridor through DuPage County, between Villa Park and West Chicago. About the...
IL 12.7 mi Crushed Stone
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...
IL 3.5 mi Asphalt
The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. The 58-mile trail consists of five connected trail segments with three main branches that converge at 300 S...
IL 58.52 mi Asphalt, Concrete, Crushed Stone
The Kenosha County Bike Trail runs for nearly 8 miles in two sections separated by couple miles with the city of Kenosha. About the Route The northern segment runs between 1st St....
WI 7.9 mi Asphalt
The Millennium Trail spans just over 30 miles in two disconnected segments. The trail goes through forest, farmland, and the suburban neighborhoods of Lake County with a range of surfaces, including...
IL 30.7 mi Asphalt, Concrete, Crushed Stone
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....
IL 11.4 mi Asphalt, Crushed Stone
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,...
WI 7 mi Asphalt
The North Branch Trail follows the North Branch of the Chicago River for 25.5 miles through Cook County. The trail was originally a dirt path often used for horseback riding; though it’s now paved, an...
IL 25.5 mi Asphalt
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...
WI 3 mi Asphalt
The Oak Leaf Trail is the jewel in the crown of Milwaukee County’s extensive trail system. The trail meanders for 123 miles in and around the city of Milwaukee on a changing terrain of flat rural...
WI 123.6 mi Asphalt
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...
WI 30.1 mi Asphalt
Accordion
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...
IL 9.6 mi Asphalt, Concrete
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...
IL 26.4 mi Asphalt, Crushed Stone, Dirt, Gravel
Just 1 mile long, the Valley Line Trail—also known as the Sauganash Trail—extends between Bryn Mawr Avenue and Devon Avenue in the Chicago neighborhood of Sauganash. Two bridges allow for safe...
IL 1.1 mi Asphalt
Although short, the West Allis Cross Town Connector represents an important start to a future link between three trails in Milwaukee County. The trail leaves from a junction with the New Berlin...
WI 0.9 mi Asphalt
The West Branch DuPage River Trail is a 26-mile regional trail that stretches between the North Central DuPage Regional Trail at its northern end and the DuPage River Trail at its southern end. The...
IL 26 mi Gravel
The White River State Trail is a 19.7-mile trail 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...
WI 19.7 mi Concrete, Crushed Stone, Gravel
The Beerline Trail, named after the corridor that was once used by freight trains transporting the ingredients for beer to some of Milwaukee’s famous breweries, runs for 3.7 miles through central...
WI 3.7 mi Asphalt
The Buffalo Creek Trail makes a 5.5-mile loop around the scenic Buffalo Creek Forest Preserve in Long Grove. The crushed-gravel trail provides access to facilities throughout the park. About the...
IL 5.5 mi Crushed Stone, Gravel
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,...
IL 3.2 mi Asphalt
The 6.5-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...
IL 6.5 mi Asphalt, Concrete, Crushed Stone
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...
WI 14 mi Asphalt, Concrete, Crushed Stone
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...
IL 13.9 mi Asphalt, Crushed Stone
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...
WI 4.6 mi Crushed Stone
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...
WI 7.5 mi Crushed Stone, Dirt, Gravel
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. About the Route The trail is one of dozens in the...
IL 7.7 mi Asphalt, Crushed Stone
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...
IL 9.2 mi Asphalt
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...
WI 6 mi Dirt, Grass
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...
WI 1.8 mi Crushed Stone, Dirt
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...
WI 3.5 mi Asphalt
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...
IL 25.4 mi Asphalt, Concrete, Crushed Stone
The Seven Waters Bike Trail is a scenic corridor stretching more than 18 miles north–south between Burlington and Muskego Lake into Waukesha County. The trail was originally three trails, locally...
WI 18.6 mi Asphalt, Crushed Stone, Gravel
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...
IL 1.5 mi Asphalt
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....
IL 3 mi Asphalt, Concrete
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,...
IL 1.1 mi Asphalt
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...
IL 4.2 mi Asphalt
The 8.9-mile 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 Lake Geneva Bike...
WI 8.9 mi Asphalt

Recent Trail Reviews

Racine County Bike Trail

Out there on it's own like an island

October, 2026 by kriekkoff_tl

The 12-foot-wide asphalt surface is in great condition. The trail hugs the road past two SC Johnson campuses as well as some government buildings. No shade and not a connector trail. Kind of out there on its own - like an island.

Racine-Sturtevant Trail

Cross at your own peril

October, 2026 by kriekkoff_tl

The 12-foot-wide asphalt trail was smooth overall with nicely mowed sides. There is a nice wooded section to the west, a road section in the middle and a hilly section on the eastern half of the trail that shares the same corridor as the powerline. There are no mile markers and no shade for most of the trail. This trail conveniently connects the Pike River Pathway to the North Shore Trail. There is one controlled intersection, but you will need to take caution when crossing the other roads along the trail.

KR Trail

Nice Connector Trail

October, 2026 by kriekkoff_tl

Although the trail has a smooth surface, it does run next to a busy highway. The main purpose of this trail, however, was to safely connect the Pike River Pathway to the Kenosha County Bike Trail. There is a very nice boardwalk on the south end of the trail!

Accordion

Pike River Pathway

Pleasantly Quiet

October, 2026 by kriekkoff_tl

The 12-foot-wide asphalt surface had some cracks, but was good overall. The trail was relatively flat with good signage. There were some busy roads to cross, but all did so at controlled intersections. I was pleasantly surprised how quiet the ride was as I biked through both prairie and industrial sections. There were no mile markers. The south end of the trail connects conveniently with the KR Trail. There is a parking lot located at the south end of the trail at Highway 195 that is not listed on the Trail Link map.

Lake Andrea Multi-Use Path

Easy Rider

October, 2026 by kriekkoff_tl

The trail was flat and smooth. The 9-foot-wide asphalt trail that circled the entire lake was unshaded, but provided spectacular and unobstructed views of the lake. Great trail for kids!

Prairie Farms Trail

Bumpy Ride

October, 2026 by kriekkoff_tl

It appeared that a load of crushed stone was recently added to the trail. A grader was used to level and spread out the stone, but ruts were left by the truck tires and the grader making the ride a little too bumpy unless you hugged the side of the trail where the grader did not reach. I enjoyed the route which meandered through cornfields, woods and prairie. The ride was peaceful, but there was no shade and I had to swat a few mosquitos when I stopped. There was an 8-car asphalt parking lot with porta potty near the north end of the trail that was not listed in TrailLink.

Ice House Trail

Nice Short Trail

October, 2026 by kriekkoff_tl

The 12-foot-wide asphalt surface had some tree root-raised areas, but manageable. The middle section of the route was a nicely paved road dedicated to wastewater treatment plant traffic. The southwestern section of the trail was nestled nicely behind backyards. The sides of the trail were mowed and the trail corridor itself was not only spacious, but nicely captured beneath a canopy of trees. The trail was a little out of the way, but I highly recommend it if you happen to be in the area.

Glacial Drumlin State Trail

Beautiful sunny October ride

October, 2026 by redpine2001

Completed my final leg of this trail by riding from London to Cottage Grove today. Trail conditions were very good, however the bridges can use some maintenance. All have matting across them to assist in preventing flats, however watch your approach, there can be some serious bumps getting onto & off the bridges. Having ridden the entire trail now, eastern portion several times; it’s just my opinion that the western portion would be my recommendation. East of Douseman the trail is paved, however much of it is in need of maintenance to remedy cracks.

White River State Trail

Pleasant Surprise

September, 2026 by dsjr2

Scenic, very pleasant ride today. Farmland, lots of bridges, packed gravel so no surprises. Parked at the Elkhorn trailhead and biked to Burlington and back. Note: the DNR site says there's a bridge out, as of 9/27/26 - there are no bridges out. Really nice ride and great way to spend a 70 degree and sunny day in late September.

Fox River Trail (IL)

Wonderful Trail

September, 2026 by nevogamer_tl

We rode the Fox River Trail over two days in September 2026. We did a short ride from St Charles to South Elgin and back one the first day, followed by a ride to Aurora and then on to part of the Illinois Prairie Path before returning to St Charles. The trail was in excellent shape and, for the most part, was well marked. We thought the scenery was better going south, with lots of water fowl, flowers and points of interest to enjoy. This trail lived up to its expectations.

Robert McClory Bike Path

September 2026 Ride

September, 2026 by dpott

I just rode from my Chicago home to Racine on the North Shore Channel, Green Bay, R McClory and Kenosha County trails. The McClory is newly paved and well signed from the Great Lakes Naval Station north to the state line. There are no facilities other than the occasional bench, and there are long stretches without any shade. Otherwise it is a terrific ride!

Kenosha Pike Bike Trail

Spectacular Lake Views

September, 2026 by kriekkoff_tl

The trail starts unassumingly in a residential neighborhood to the north and winds its way through Carthage College before bursting out of a canopy of trees into a spectacular, unobstructive view of Lake Michigan. The trail hugs the coast and meanders through a series of gorgeous parks. Just when your senses have almost reached their limit, you find yourself riding along Harbor Park filled with an assortment of sculptures, museums, and marinas. The Park is electric!
This was the most enjoyable ride I have ever taken. I will be back!
There are two cautionary notes, however.
1. The city roads between Poerio Park West and upper Alford Park are in horrible condition. Maybe avoid this northern section altogether.
2. The trail that goes south from the 50th Street bridge as you enter the Harbor is actually a staircase. I missed it the first time, but realized it on my return. There is a very steep embankment with a thin bike path next to the stairs, if you want to risk it.

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