Middleton, WI Snowmobiling Trails and Maps

500 Reviews

Looking for the best Snowmobiling trails around Middleton?

Find the top rated snowmobiling trails in Middleton, 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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12 Results
Activities
Length
Surfaces
Type

400 State Trail

21.9 mi
State: WI
Crushed Stone

Glacial Drumlin State Trail (Route of the Badger)

53.2 mi
State: WI
Asphalt, Crushed Stone, Gravel

Jane Addams Trail

18.9 mi
State: IL
Asphalt, Crushed Stone

Wolf Run Trail (WI)

2 mi
State: WI
Crushed Stone

Badger State Trail

39.8 mi
State: WI
Asphalt, Crushed Stone

Cheese Country Recreation Trail

46.4 mi
State: WI
Crushed Stone, Dirt, Gravel

Military Ridge State Trail

40 mi
State: WI
Asphalt, Crushed Stone

Pecatonica State Trail

10 mi
State: WI
Crushed Stone

Pelishek-Tiffany Nature Trail

6 mi
State: WI
Dirt, Grass

Pine River Trail

14.3 mi
State: WI
Boardwalk, Crushed Stone, Dirt, Grass

Sugar River State Trail

22.7 mi
State: WI
Asphalt, Crushed Stone

Wild Goose State Trail

34.5 mi
State: WI
Asphalt, Crushed Stone, Dirt, Grass
Trail Image Trail Name States Length Surface Rating
Overview Traveling the 400 State Trail is a numbers game. The trail’s name refers to the old Chicago and North Western Railway’s “No. 400” passenger train that zoomed through here between Chicago...
WI 21.9 mi 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
Overview The Jane Addams Trail runs for 18.9 miles between Orangeville and Freeport, following a rail line that the Illinois Central built in 1887 between Freeport, Illinois, and Madison,...
IL 18.9 mi Asphalt, Crushed Stone
The Wolf Run Trail supports a wide variety of users on its two miles of crushed gravel, situated on the outskirts of Mazomanie in northwestern Dane County. Heading southeast from the charming...
WI 2 mi Crushed Stone
Closure Notice: The Stewart Tunnel has been closed since 2019 and remains closed for the foreseeable future. A detour using Tunnel Road allows trail users to go around the tunnel. Visit the trail page...
WI 39.8 mi Asphalt, Crushed Stone
Overview    Most suited for ATVers, snowmobilers and motorized trail-bikers, the Cheese Country Recreation Trail, also knowns as the Tri-County Trail, spans 47-miles through Wisconsin’s rugged...
WI 46.4 mi Crushed Stone, Dirt, Gravel
NOTE: A State Trail Pass ($25 annually/$5 daily) is required for bicyclists and in-line skaters ages 16 and older. Snowmobilers must display either a Wisconsin registration or a snowmobile State Trail...
WI 40 mi Asphalt, Crushed Stone
The Pecatonica State Trail is never far from water as it takes the easygoing Bonner Branch Valley through the rolling hills and rocky bluffs of southwest Wisconsin’s Driftless Area, a region that the...
WI 10 mi Crushed Stone
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
The Pine River Trail winds on an abandoned railroad corridor between Richland Center and Lone Rock in scenic Richland County. Trail users are treated to stunning views of river bluffs, marshland and...
WI 14.3 mi Boardwalk, Crushed Stone, Dirt, Grass
Overview If you can’t make it to Switzerland, then you can do the  next best thing: take the Sugar River State Trail to “America’s Little Switzerland,” New Glarus, Wisconsin. Settled in 1845 by a...
WI 22.7 mi Asphalt, Crushed Stone
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 ¿

Badger State Trail

Serenity

October, 2024 by ggroth99

Coming from Chicago, we have only ridden this trail as a day trip and ridden from Orangeville, IL (Jane Addams Trail) to Monroe (Twining Park) and back. This stretch is on a slight incline most of the way from Orangeville to Monroe, so the ride back is a lot easier. Trail is well maintained, and mostly shaded by trees. Trail in Monroe proper was a little dicey due to no protection from the elements, a bit of a steep hill, and a lot of runoff from rain by 8th street. Crossing at 8th street is "interesting". Pit toilet in Orangeville, with a BP gas station right across the road, flush toilet in Twining Park. Went riding on 10/26, and saw a grand total of 5 other people the entire ride (2 bikers, 2 walkers, 1 jogger). Only trail I've been on where there were complete moments of silence, combined with some of the scenery, just absolutely breathtaking.

Jane Addams Trail

Great trail

October, 2024 by ggroth99

Have ridden this trail multiple times over the past couple of years. Generally ride from the trailhead by Hwy 20 to Orangeville. Trail is well maintained and generally flat, and fairly empty of people, a few joggers on the South end. As with all the limestone trails, there's a few holes here and there from the local furry creatures. Pit toilets at Hwy 20 & Orangeville, a portolet at Red Oak. There's a BP gas station right across from the pavilion in Orangeville. Specific highlights are the old buildings from the railroad in Scioto Mills, and saw sand cranes inhabiting the wetlands south of Orangeville.

Accordion

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!

Jane Addams Trail

Beautiful and quiet

October, 2024 by shanlalond

Rode our hybrids from Freeport Public Library to trail and followed it to the state line. Found it to be well maintained, flat and very little bike traffic. We biked on a Friday morning. FYI the library has paper maps of the trail.

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.

Great Sauk State Trail

I have ridden this trail a couple of times and have enjoyed the trail quality and the river and prairie scenery. The only complaint I have is that the trail ends before getting into Devils Lake State Park which could make the trail spectacular.

October, 2024 by mankato

I have ridden this trail a couple of times and have enjoyed the trail quality and the river and prairie scenery. The only complaint I have is that the trail ends before getting into Devils Lake State Park which could make the trail spectacular.

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.

400 State Trail

We will return to the 400

September, 2024 by ellaqk_tl

We had ridden into Elroy from Sparta and realized the 400 trail left from there. We went back to Elroy two days later and rode 11 miles out on the 400. We went through Union and through Wonewoc. We were so impressed with the little town of Wonewoc and the super clean facility they had along the trail, that included a picnic shelter and water fountain along with bike repair stands. The ride itself was very nice. The trail was well cared for and there were many bridges that overlooked very pretty areas. We passed several large rock formations that were impressive. We hope to return to the area so we can ride the entire trail.

400 State Trail

We will return to the 400

September, 2024 by ellaqk_tl

We had ridden into Elroy from Sparta and realized the 400 trail left from there. We went back to Elroy two days later and rode 11 miles out on the 400. We went through Union and through Wonewoc. We were so impressed with the little town of Wonewoc and the super clean facility they had along the trail, that included a picnic shelter and water fountain along with bike repair stands. The ride itself was very nice. The trail was well cared for and there were many bridges that overlooked very pretty areas. We passed several large rock formations that were impressive. We hope to return to the area so we can ride the entire trail.

Badger State Trail

Nice Views

September, 2024 by the_masseuse

Trail is really nice and taken care of. There are a a few sand traps along it tho. It’s mostly shaded until you reach the asphalt. Decent parking along it. I very much dislike the detour on this trail..it’s super hilly. Really regret coming to see the tunnel while still open.

Great Sauk State Trail

awesome relaxing ride

September, 2024 by 49zhs7nbgx

It’s a well maintained, paved trail with markers and sculptures along the way. The scenery is beautiful!!

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