Caledonia, WI Snowmobiling Trails and Maps

1008 Reviews

Looking for the best Snowmobiling trails around Caledonia?

Find the top rated snowmobiling trails in Caledonia, 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.

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Activities
Length
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Type
7 Results
Activities
Length
Surfaces
Type

Des Plaines River Trail

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

Eisenbahn State Trail

24.3 mi
State: WI
Asphalt, Crushed Stone

Glacial Drumlin State Trail

53.2 mi
State: WI
Asphalt, Crushed Stone, Gravel

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 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 Eisenbahn State Trail gives a nod to Wisconsin’s German heritage in its name—Eisenbahn is German for “railway.” The strict translation, “iron road,” refers to the iron rails originally used as...
WI 24.3 mi Asphalt, 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
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

Pelishek-Tiffany Nature Trail

All grass. Best for walkers not bikes.

August, 2026 by scb324

All grass. Best for walkers not bikes.

Powerline Trail (WI)

Powerline trail is great!

August, 2026 by ljkjmk

Crossing roads can be tricky but most drivers are willing to let you pass.

City of Franklin Hike and Bike Trail

Busy Traffic

August, 2026 by kriekkoff_tl

Although the meticulously maintained 8-foot wide asphalt trail is short, one must cross W Forest Home Avenue twice. The traffic was fast and constant. I was lucky enough to attract a courteous driver who stopped for me, so I could make it across safely. Not a good trail for the young ones. The rating of the trail would have been 5 stars, but the traffic crossings brought it down a notch.

Accordion

Kinnickinnic River Trail

3-section trail

August, 2026 by kriekkoff_tl

This 8 foot-wide asphalt trail was beautiful when I first rode it several years ago. The 3 sections of trail are connected by roads. One must cross 2 busy roads to get to the middle section from the southern section and there is no signage to guide you. The southern section is also poorly maintained; the grass is not mowed on either side of the trail and the tree branches and bushes overhead make the 8 foot wide trail seem smaller. I still bike this trail quite often, because it is a safer and a more scenic route to travel from my house to downtown.

Beerline Trail

Short and Sweet

August, 2026 by kriekkoff_tl

This 8 foot-wide asphalt trail meanders through urban neighborhoods. Although the trail is broken up in a few sections by roads, there is plenty of unique artwork to see. My favorite ride in the city!

West Allis Cross Town Connector

The West Allis Connection, not the French Connection

July, 2026 by kriekkoff_tl

This well maintained asphalt trail is a nice extension of the New Berlin Trail.
At the midway point, one must exit the trail and ride down to 116th Street, then ride back up to the trail on the other side. What would it take to extend this trail further east?

Jefferson County Interurban Trail

Hidden Gem

July, 2026 by kriekkoff_tl

Even though the sides of the trail were not mowed, the asphalt surface was in great condition. Beautiful views of the surrounding farmland. The trail is basically straight with slight grade changes between roads. Another 3 miles of asphalt trail have been added to the east past Ski Slide Road in Oconomowoc. A crushed gravel trail continues east to Second Street, but this looks like the base for the asphalt that should be added by fall.

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.

Glacial River Trail

a lot of road riding

June, 2026 by 47gkpg2wy5

We took this trail from the Wild Goose trail but had no idea we would be on so many roads. As you got closer to Watertown, you are also on the road. We personally try to avoid roads as much as possible so we didn’t like this part. We only went to Watertown from the North so I am not sure what the rest of the trail is like. The actual bike paths are great.

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.

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