Pleasant Prairie, WI Snowmobiling Trails and Maps

1289 Reviews

Looking for the best Snowmobiling trails around Pleasant Prairie?

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

  • Relevance
  • Name
  • Length
  • Most Popular
Activities
Length
Surfaces
Type
8 Results
Activities
Length
Surfaces
Type

Busse Woods Trail

11.6 mi
State: IL
Asphalt, Concrete

Des Plaines River Trail

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

Glacial Drumlin State Trail

53.2 mi
State: WI
Asphalt, Crushed Stone, Gravel

Great Western Trail (DeKalb, Kane)

18 mi
State: IL
Asphalt, Crushed Stone

Hebron Trail

6.7 mi
State: IL
Crushed Stone, Gravel

Prairie Trail (IL)

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

White River State Trail

19.7 mi
State: WI
Concrete, Crushed Stone, Gravel

Pelishek-Tiffany Nature Trail

6 mi
State: WI
Dirt, Grass
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 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 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
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 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....
IL 6.7 mi Crushed Stone, Gravel
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
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 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

Recent Trail Reviews

Prairie Trail (IL)

Illinois perfection

July, 2026 by ericevan

Bike type: Hybrid (Specialized Sirus 2019)
Conditions: mid-70's, light breeze, dry
Segment biked: Just south of Algonquin to Barnard Mill Rd (north of McHenry) = 40 miles

I started my ride around 9:30am on a July Friday. I had biked a few miles of the trail just north of downtown Algonquin before, the rest was new to me. Perfect conditions motivated me in every way. Perfect temps, full sun, and breeze kept me going for my longest ride since 1997.
The entire path that I rode was asphalt. There are a couple of deviations through downtown areas when you're on sidewalks or streets. But everything was paved. Riding from town to town has always been a favorite, but the Prairie trail gie you even more than that. North of Crystal Lake you'll find miles on end of straight path and very little to see except nature. There's also Sterne's Woods, which really threw me for a loop. Can't say I've ever seen signs that tell bikers to dismount. Then you find out why. There are several hills back here to test your fortitude. At least three hills look to be close to a 45-degree angles. If you're riding these as I did, be careful and make sure you're only tempting them in optimal conditions (dry, no wind). Just coasting pushed me close to 40mph. These hills are as tough as they come to climb in Illinois. Algonquin, Crystal Lake and McHenry all offer pitstops if you need one. I saw two other parking lots away from the towns with benches and bathrooms. I had read from other reviewers that the path north of Barnard Mill Rd was gravel and dicey, so I didn't tempt that. My hybrid tires can hold their own, but it only takes one sharp piece of gravel to strand you far from your starting point. All in all, this path is a 10 out of 10 in my opinion. It's extremely well kept up, very diverse, ridable for any type of bike, with amenities and beauty along the way.

Bugline Trail

Nice paved trail except for all the road crossings at the south end

July, 2026 by y1htak2

We started in downtown Menomonee Falls. We parked in Mill Pond Park on Roosevelt, then rode our bike over to Water Street where the trail begins. That probably wasn’t the best place to start because we had to cross the two scary intersections; Highway 175 with a crossing light and Main street on a long diagonal with no crossing light.

This is a very nice trail with wooded areas that pass through residential areas and some business areas. The northern end has some fields. On the southern end you have to stop to cross at a lot of roads all the way to and through Sussex. Luckily the car drivers are very courteous and stop to let you cross. It was nice to see kids of all ages on the trail. It’s pretty flat until you get past the Fireman’s Park soccer fields in Merton. Then you have some pretty steep hills.

Lake Geneva Bike Path

Agree with other Reviews

July, 2026 by jboepple

Poorly marked. Several sections are in need of repair. Several unexpected "end of trail" dead ends. Very disappointed. Wish a safe route was created to hook up with the White River State Trail, which is only a few miles away, but to access it you need to traverse country roads posted at 55 MPH and with little to no shoulder.

Accordion

Seven Waters Bike Trail

flat

June, 2026 by sterp8

I think it was a nice trail. We started out in Rochester and went north Very flat so there is constant pedaling. Good signage. No bathrooms until Meyer Park or Heg park and pray they are open.

White River State Trail

Update!

June, 2026 by b7ggzfh8h9

As of June 15th, the trail is now open between Burlington and Lyon.

Millennium Trail (IL)

Review of Northern Section

June, 2026 by tandemlovers

We rode the entire northern section this spring. 10 miles one way. Best place to park if you want to start in Round Lake Beach is the Round Lake Beach Elementary School parking lot. It's about a block and a half off the trail near the west terminus.
Most of the trail is well manicured fine limestone. Very good condition throughout. Scenery is excellent.
The signage is ok. Some intersections are well marked and others not marked at all.
There are several spur loops and many neighborhood access spurs. Use a map, these can get very confusing.
It loses a star for the signage and some rather intimidating grade crossings near the west end.

White River State Trail

Between Spring Valley road trailhead and Lyon the trail was closed due to 2 bridges being washed out

May, 2026 by fredklausegger

Between Spring Valley road trailhead and Lyon the trail was closed due to 2 bridges being washed out

Muskego Recreation Trail

Beautiful trail with varying gravel conditions

May, 2026 by nkanute

great gravel cycling! Everyone complaining must be riding some skinny tires or should stick to the oak leaf- this was a very fun ride (I run 40mm semi slick tires and had no issues)

Moraine Hills State Park Trail

My wife and I just purchased two e-Bikes and decided to use this place for our maiden voyage. This was also our first time at this state park. We really enjoyed the tails and the nature. We will be returning with cameras and fishing poles.

May, 2026 by garyboutte

My wife and I just purchased two e-Bikes and decided to use this place for our maiden voyage. This was also our first time at this state park. We really enjoyed the tails and the nature. We will be returning with cameras and fishing poles.

Northwestern University Lakefill

a simple, short loop

May, 2026 by vivekipsingh

Simple, short loop. You will end up sharing the loop with a lot more people when the weather gets good

Kenosha County Bike Trail

Lots of shade and well maintained

April, 2026 by gypsycyn

A short but pleasant ride, with lots of shade, smaller wildlife, rest benches, even a couple pet stops with water dishes for the fur babies.

H.U.M. Trail

My honey had not.rode a bike in many years and didn't want to ride around a lot of people. So when we found this trail it became a favorite, very few people, flat, nice flowers and views. The parking is really easy at both ends.

April, 2026 by dambrisco

My honey had not.rode a bike in many years and didn't want to ride around a lot of people. So when we found this trail it became a favorite, very few people, flat, nice flowers and views. The parking is really easy at both ends.

Find Nearby City trails

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.