Waukesha, WI Snowmobiling Trails and Maps

781 Reviews

Looking for the best Snowmobiling trails around Waukesha?

Find the top rated snowmobiling trails in Waukesha, 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
8 Results
Activities
Length
Surfaces
Type

Des Plaines River Trail

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

Eisenbahn State Trail (Route of the Badger)

24.3 mi
State: WI
Asphalt, Crushed Stone

Glacial Drumlin State Trail (Route of the Badger)

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 (Route of the Badger)

19.7 mi
State: WI
Concrete, Crushed Stone, Gravel

Pelishek-Tiffany Nature Trail

6 mi
State: WI
Dirt, Grass

Wild Goose State Trail

34.5 mi
State: WI
Asphalt, Crushed Stone, Dirt, Grass
Trail Image Trail Name States Length Surface Rating
Overview 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...
IL 56.1 mi Asphalt, Crushed Stone, Dirt, Gravel
Overview 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...
WI 24.3 mi Asphalt, Crushed Stone
Overview 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...
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
Overview 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...
IL 26.4 mi Asphalt, Crushed Stone, Dirt, Gravel
Overview 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...
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
Overview The Wild Goose State Trail is a premier rail trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. For trail users looking for a peaceful and beautiful place to visit,...
WI 34.5 mi Asphalt, Crushed Stone, Dirt, Grass

Recent Trail Reviews

Wild Goose State Trail

Lovely Trail

November, 2024 by the_masseuse

It’s pretty scenic, especially with the leaf colors. Also pretty busy! There’s parking on both ends. A lot of the trail is grass, not even gravel. The spot where it’s asphalt is very minimal. It’s awesome you can stop and ride through Horicon Marsh! Lots of kitties on this trail ¿

Jefferson County Interurban Trail

stunning and peaceful

October, 2024 by wilsonae

Just kept riding. Gorgeous fall day. Started at northern trailhead. Passed a few walkers and one other biker the whole way to the end. As noted it has been extended well past 2.2 miles. Lovely scenery and immaculate trail surface with lots of peaceful farms. My new fave!

Long Prairie Trail

Disappointed

October, 2024 by deetiffanylb

Like all rails to trails, a good connector for locals but for bike touring, tedious. Boring, straight, only a few peeks of rolling farm land to catch your eye, when it wasn't on the trail - immediately in front of you. Sections of the trail are in jaw-jarring condition. Beware: with leaf litter you can not see the periodic holes, non existent bridge transitions, broken asphalt...you get idea. Sad that some entity can not repair these hazards. We def would not continue west, beyond Poplar Grove. Our bodies can't take it!

Accordion

Glacial Drumlin State Trail (Route of the Badger)

Great trail, but there's a temporary closure

October, 2024 by sarahccaltvedt

We rode about 23 miles round-trip from the Waukesha trailhead on Oct. 12. The asphalt is in pretty good condition, with just a few bumps. However, when we got to the big curve around what used to be a field east of Dousman, we discovered that the field is now a massive construction site, and the trail is closed indefinitely, with no posted detour. We don't take our tandem on roads, so we turned around at that point. I assume that the trail is open west of the construction site, but don't know exactly where.

We didn't ride on the western portion of the trail that day, but it's one of our favorites, especially the part where you bike across the lake.

Powerline Trail (WI)

New trail, is very smooth. Crossing streets is safe. Slight uphill grade west to east which makes return trip west easy!

October, 2024 by lagerke

New trail, is very smooth. Crossing streets is safe. Slight uphill grade west to east which makes return trip west easy!

Glacial Drumlin State Trail (Route of the Badger)

There are several areas in which there are tire ruts and the trail is too narrow. Diffently not worth the daily fee of $5.00.

September, 2024 by dq82

There are several areas in which there are tire ruts and the trail is too narrow. Diffently not worth the daily fee of $5.00.

Robert McClory Bike Path

Thoughts Of This Trail Getting Paved, And The Lack Of People Getting Caught Using Motorized Bikes!

September, 2024 by ij3175974

Good News! This Path Is Finally Going To Get Paved Soon, Between 2025 And 2026. I Can't Wait To See How This Path Turns Out, And I'm Ready For This Trail To Be Like The Kenosha County Bike Trail. I'm Glad They Are Doing This, Because I've Caught Several People Speeding On This Trail With Dirt Bikes, And I Think It's Annoying And Dangerous. The Signs Say No Equestrian, And Motorized Vehicles On The Trail, And People Don't Listen. Till This Day, People Still Ride These Motorized Vehicles On This Trail, Including The Waukegan Savanna Trail, Which Is Connected Right By The Trail Intersection In Beach Park, Right Next To The Lyons Woods Forest Preserve. Today, I Saw This One Person Speeding With A Dirt Bike On The Waukegan Savanna Trail, And I Was About To Film Him And Report Him To The Police. If I Catch More People Doing It, I Will Start Recording, And Reporting It To The Police, Because That Should Be Illegal. Overall, I Ride This Trail Often To Visit The Waukegan Airport, To Do A 10 Mile Round Trip Ride, Just Looking Forward To Seeing This Trail Paved, Hopefully In Spring 2025. Be Safe Guys!

Hank Aaron State Trail (Route of the Badger)

Nice easy trail

September, 2024 by joenad55

Ran parts of this trail recently. Easy paved trail through wooded area. Some shade in early morning hours.

Prairie Trail (IL)

Water fountain removed

September, 2024 by elissasteglich

The water fountain noted on the map at Hillside Rd no longer exists. Looks like it was taken out.

Oak Leaf Trail (Route of the Badger)

Great trail!

September, 2024 by nadia.rasberry01

Well maintained trail, no garbage or anything on the path! Was great for walking with a stroller there was one roughest patch we hit but that was it. Amazing views and a nice breeze from the water. Very active trail, pretty busy area.

Ozaukee Interurban Trail (Route of the Badger)

This has to be one of the top 2 or 3 bike routes in the greater Milwaukee area.

September, 2024 by zero2epiphany

I have ridden this from Brown Deer to just a bit past Port Washington and still need to do the whole thing. On the Soutern side where it starts its no different than say, Zipline or the Brown Deer connector. But once you start getting close to Cederburg, it starts to shine, with a dip in scenery when you transition through Grafton. Then the trail SHINES BRIGHT right into Port Washington. This and Bugline are probably my favorite rides in the greater Milwaukee area.

New Berlin Recreation Trail

Great for strollers!

September, 2024 by nadia.rasberry01

This trail is beautiful, it’s very smooth and works great for if you have a kiddo in a stroller! Lots of wildlife, we saw birds, bunny’s, squirrels, chipmunks, and 2 foxes!

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