Freeport, IL Snowmobiling Trails and Maps

489 Reviews

Looking for the best Snowmobiling trails around Freeport?

Find the top rated snowmobiling trails in Freeport, 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
13 Results
Activities
Length
Surfaces
Type

Badger State Trail

40 mi
State: WI
Asphalt, Crushed Stone

Cheese Country Recreation Trail

47 mi
State: WI
Crushed Stone, Gravel

Hennepin Canal Parkway

104.5 mi
State: IL
Asphalt, Grass, Gravel

Jane Addams Trail

18.9 mi
State: IL
Asphalt, Crushed Stone

Joe Stengel Trail

7.9 mi
State: IL
Ballast, Grass, Gravel

Kinstone Recreational Path

0.6 mi
State: IL
Asphalt, Crushed Stone, Gravel

Lowell Parkway Trail

3.5 mi
State: IL
Asphalt

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

Riverside Recreational Path

0.63 mi
State: IL
Dirt, Grass, Gravel

Stone Bridge Trail

5.8 mi
State: IL
Crushed Stone

Sugar River State Trail

22.7 mi
State: WI
Asphalt, Crushed Stone
Trail Image Trail Name States Length Surface Rating
Rail-trail fans know that Wisconsin’s Elroy-Sparta State Trail is famous for its three tunnels. The Badger State Trail, which heads south from Madison to the Illinois state line (where it connects...
WI 40 mi Asphalt, Crushed Stone
If you’re looking for an invigorating motorized-trail experience, the Cheese Country Recreation Trail (aka the Tri-County Trail) won’t disappoint. If you’re on foot, hoof, or self-propelled two...
WI 47 mi Crushed Stone, Gravel
The Hennepin Canal Parkway, administered by the Illinois Department of Natural Resources as a state park, follows an old towpath along a canal opened in 1907 and quickly abandoned due to competition...
IL 104.5 mi Asphalt, Grass, Gravel
There’s no debating the historical significance of the Jane Addams Trail. Not only is it named for a Nobel Peace Prize-winning social activist who grew up nearby, but the trail also passes the site of...
IL 18.9 mi Asphalt, Crushed Stone
The Joe Stengel Trail follows an old railroad corridor for 7 miles between the town of Polo and the much smaller community of Woosung. The trail corridor traces farm country along a route scattered...
IL 7.9 mi Ballast, Grass, Gravel
From Main Street and Elevator Road in Roscoe, the scenic Kinstone Recreational Path winds its way northeast through woodlands along the north branch of Kinnikinnick Creek to the Stone Bridge Trail....
IL 0.6 mi Asphalt, Crushed Stone, Gravel
The Lowell Parkway Trail runs through the charming town of Dixon, Illinois, boyhood home of Ronald Reagan. The trail occupies the rail bed of the old Illinois Central Railroad, between Lowell Park and...
IL 3.5 mi Asphalt
The Military Ridge State Trail finds the high ground as it rolls across 40 miles of idyllic farmland from the outskirts of Madison to the historic mining town of Dodgeville. It follows an American...
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 Riverside Recreational Path begins as a gravel lane at the base of Riverside Park on the banks of the Rock River in Roscoe. From there, it continues along Rowena Street, paralleling State Route...
IL 0.63 mi Dirt, Grass, Gravel
Built on a former rail bed dating back to the 1850s, the Stone Bridge Trail provides a crushed limestone pathway through rural countryside. A highlight of the trail is passage on Stone Bridge over the...
IL 5.8 mi Crushed Stone
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 small group...
WI 22.7 mi Asphalt, Crushed Stone

Now, More Than Ever, Trails Matter!

During COVID-19, trails are being counted on as places where people can find solace and respite and we need your support to keep trails open and provide these critical FREE resources! Please continue to practice physical distancing and check the status of your trail before heading out!

Trails by activity

Military Ridge State Trail

WI - 40 miles

The Military Ridge State Trail finds the high ground as it rolls across 40 miles of idyllic farmland from the outskirts of Madison to the historic mining town of Dodgeville. It follows an American...

Lowell Parkway Trail

IL - 3.5 miles

The Lowell Parkway Trail runs through the charming town of Dixon, Illinois, boyhood home of Ronald Reagan. The trail occupies the rail bed of the old Illinois Central Railroad, between Lowell Park and...

Riverside Recreational Path

IL - 0.63 miles

The Riverside Recreational Path begins as a gravel lane at the base of Riverside Park on the banks of the Rock River in Roscoe. From there, it continues along Rowena Street, paralleling State Route...

Jane Addams Trail

IL - 18.9 miles

There’s no debating the historical significance of the Jane Addams Trail. Not only is it named for a Nobel Peace Prize-winning social activist who grew up nearby, but the trail also passes the site of...

Accordion

Sugar River State Trail

WI - 22.7 miles

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 small group...

Stone Bridge Trail

IL - 5.8 miles

Built on a former rail bed dating back to the 1850s, the Stone Bridge Trail provides a crushed limestone pathway through rural countryside. A highlight of the trail is passage on Stone Bridge over the...

Kinstone Recreational Path

IL - 0.6 miles

From Main Street and Elevator Road in Roscoe, the scenic Kinstone Recreational Path winds its way northeast through woodlands along the north branch of Kinnikinnick Creek to the Stone Bridge Trail....

Hennepin Canal Parkway

IL - 104.5 miles

The Hennepin Canal Parkway, administered by the Illinois Department of Natural Resources as a state park, follows an old towpath along a canal opened in 1907 and quickly abandoned due to competition...

Badger State Trail

WI - 40 miles

Rail-trail fans know that Wisconsin’s Elroy-Sparta State Trail is famous for its three tunnels. The Badger State Trail, which heads south from Madison to the Illinois state line (where it connects...

Pelishek-Tiffany Nature Trail

WI - 6 miles

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...

Badger State Trail

WI - 40 miles

Rail-trail fans know that Wisconsin’s Elroy-Sparta State Trail is famous for its three tunnels. The Badger State Trail, which heads south from Madison to the Illinois state line (where it connects...

Military Ridge State Trail

WI - 40 miles

The Military Ridge State Trail finds the high ground as it rolls across 40 miles of idyllic farmland from the outskirts of Madison to the historic mining town of Dodgeville. It follows an American...

Stone Bridge Trail

IL - 5.8 miles

Built on a former rail bed dating back to the 1850s, the Stone Bridge Trail provides a crushed limestone pathway through rural countryside. A highlight of the trail is passage on Stone Bridge over the...

Accordion

Pecatonica State Trail

WI - 10 miles

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...

Kinstone Recreational Path

IL - 0.6 miles

From Main Street and Elevator Road in Roscoe, the scenic Kinstone Recreational Path winds its way northeast through woodlands along the north branch of Kinnikinnick Creek to the Stone Bridge Trail....

Hennepin Canal Parkway

IL - 104.5 miles

The Hennepin Canal Parkway, administered by the Illinois Department of Natural Resources as a state park, follows an old towpath along a canal opened in 1907 and quickly abandoned due to competition...

Joe Stengel Trail

IL - 7.9 miles

The Joe Stengel Trail follows an old railroad corridor for 7 miles between the town of Polo and the much smaller community of Woosung. The trail corridor traces farm country along a route scattered...

Jane Addams Trail

IL - 18.9 miles

There’s no debating the historical significance of the Jane Addams Trail. Not only is it named for a Nobel Peace Prize-winning social activist who grew up nearby, but the trail also passes the site of...

Lowell Parkway Trail

IL - 3.5 miles

The Lowell Parkway Trail runs through the charming town of Dixon, Illinois, boyhood home of Ronald Reagan. The trail occupies the rail bed of the old Illinois Central Railroad, between Lowell Park and...

Sugar River State Trail

WI - 22.7 miles

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 small group...

Riverside Recreational Path

IL - 0.63 miles

The Riverside Recreational Path begins as a gravel lane at the base of Riverside Park on the banks of the Rock River in Roscoe. From there, it continues along Rowena Street, paralleling State Route...

Cheese Country Recreation Trail

WI - 47 miles

If you’re looking for an invigorating motorized-trail experience, the Cheese Country Recreation Trail (aka the Tri-County Trail) won’t disappoint. If you’re on foot, hoof, or self-propelled two...

Joe Stengel Trail

IL - 7.9 miles

The Joe Stengel Trail follows an old railroad corridor for 7 miles between the town of Polo and the much smaller community of Woosung. The trail corridor traces farm country along a route scattered...

Cheese Country Recreation Trail

WI - 47 miles

If you’re looking for an invigorating motorized-trail experience, the Cheese Country Recreation Trail (aka the Tri-County Trail) won’t disappoint. If you’re on foot, hoof, or self-propelled two...

Riverside Recreational Path

IL - 0.63 miles

The Riverside Recreational Path begins as a gravel lane at the base of Riverside Park on the banks of the Rock River in Roscoe. From there, it continues along Rowena Street, paralleling State Route...

Sugar River State Trail

WI - 22.7 miles

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 small group...

Accordion

Lowell Parkway Trail

IL - 3.5 miles

The Lowell Parkway Trail runs through the charming town of Dixon, Illinois, boyhood home of Ronald Reagan. The trail occupies the rail bed of the old Illinois Central Railroad, between Lowell Park and...

Pecatonica State Trail

WI - 10 miles

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...

Pelishek-Tiffany Nature Trail

WI - 6 miles

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...

Military Ridge State Trail

WI - 40 miles

The Military Ridge State Trail finds the high ground as it rolls across 40 miles of idyllic farmland from the outskirts of Madison to the historic mining town of Dodgeville. It follows an American...

Badger State Trail

WI - 40 miles

Rail-trail fans know that Wisconsin’s Elroy-Sparta State Trail is famous for its three tunnels. The Badger State Trail, which heads south from Madison to the Illinois state line (where it connects...

Kinstone Recreational Path

IL - 0.6 miles

From Main Street and Elevator Road in Roscoe, the scenic Kinstone Recreational Path winds its way northeast through woodlands along the north branch of Kinnikinnick Creek to the Stone Bridge Trail....

Stone Bridge Trail

IL - 5.8 miles

Built on a former rail bed dating back to the 1850s, the Stone Bridge Trail provides a crushed limestone pathway through rural countryside. A highlight of the trail is passage on Stone Bridge over the...

Jane Addams Trail

IL - 18.9 miles

There’s no debating the historical significance of the Jane Addams Trail. Not only is it named for a Nobel Peace Prize-winning social activist who grew up nearby, but the trail also passes the site of...

Hennepin Canal Parkway

IL - 104.5 miles

The Hennepin Canal Parkway, administered by the Illinois Department of Natural Resources as a state park, follows an old towpath along a canal opened in 1907 and quickly abandoned due to competition...

Recent Trail Reviews

Pecatonica Prairie Trail

Pecatonica Prairie trail 11-07-2020

November, 2020 by terri.hagmann

My husband and I did the whole trail r/t Farewell Bridge Road to Meridian Road and back today. Good spots, and not as good spots. We rode it about two years ago, and it was very sandy in some spots. Those spots have course gravel in them now. We ride hybrid bikes with cross-terrain tires. It was ok, but fat tires work better on the grassy and course gravel areas. It needs some work, but was still an enjoyable scenic ride on a beautiful day.

Hennepin Canal Parkway

Oct. 27, 2020 30 year anniversary and we wanted just to get out. It was cold but endurable... We were impressed by our 2 hour round trip ride from the route 29 entrance. In better weather being the kids... Do some fishing.... Watch for animals.

November, 2020 by dra.wiersema

Oct. 27, 2020 30 year anniversary and we wanted just to get out. It was cold but endurable... We were impressed by our 2 hour round trip ride from the route 29 entrance. In better weather being the kids... Do some fishing.... Watch for animals.

Sugar River State Trail

Sugar River Trail

October, 2020 by wsuy5m6mtx

LOVED our ride on this trail today (early October). Scenery was beautiful and the trail was in great condition. I highly recommend to anyone wanting to experience a non-paved trail. New Glarus (America’s Little Switzerland) was also a wonderful experience. Can’t wait to do again next year!

Accordion

Badger State Trail

Badger Trail much improved from the last several years.

October, 2020 by bikeandrun

I have had some rough riding over the years with rarely cut grass. This year the DNR has shifted gears and improved this trail a lot. The best I've rode in several years. Jane Adams hooks up to the Badger at the State line. Ruts and holes have really been worked on. And weeds cut as best as they can keep up with it. I have ridden this trail many times this year.
Excellent job, DNR. Keep it up. I have also seen more people walking, jogging and riding this and the Sugar Trails this year since I started in 1986 riding.

Sugar River State Trail

Sugar River Trail, wisconsin

October, 2020 by bikeandrun

In the past I gave this a rather bad review. This year however the Wisconsin DNR and whatever other agencies help maintain this trail from Brodhead, Wi. to New Glarus have it in absolutely wonderful shape.
I heard around Brodhead it was rough. Not so this year. In fact I will ride it again the first week of Oct. 2020. The leaves and trail was a tree tunnel to heaven. Great work on this and the Badge Trail this year.

Pelishek-Tiffany Nature Trail

Beautiful tree canopies. Trail mostly grass, but biking it was no problem. Very little use, only encountered 4 other people & they were walking. Parking lot at Clinton, but only street in parking at Allen-Grove.

September, 2020 by ljleslie314

Beautiful tree canopies. Trail mostly grass, but biking it was no problem. Very little use, only encountered 4 other people & they were walking. Parking lot at Clinton, but only street in parking at Allen-Grove.

Cheese Country Recreation Trail

Tough but doable

September, 2020 by mikenue

Date of ride: 09/20/2020 Bike: hybrid with 42mm tires The Cheese Country trail, as other reviews state, is not a relaxing ride. You have to work for every mile. The gravel is large and there are lots of soft patches. I rode on a weekend so there was quite a bit of ATV traffic. All of the riders were respectful and slowed down to pass, but they kicked up a lot of dust. The 47 miles from Mineral Point to Monroe took 6 hrs. The scenery is nice, but you won’t get to enjoy it much as you’ll be focusing on the trail. If you are looking for a pleasant cerusged limestone trail

Badger State Trail

We enjoyed writing on this trail as a family. The tunnels are closed, because there were rocks falling from the ceiling (We ran into one of the employees who monitors the trails).

September, 2020 by sissijojo

We enjoyed writing on this trail as a family. The tunnels are closed, because there were rocks falling from the ceiling (We ran into one of the employees who monitors the trails).

Badger State Trail

DISAPPOINTED

September, 2020 by jkrause1125

Rode from Monroe to Monticello, and then to the Stewart Tunnel. Was told the tunnel was closed, but not monitored, so we could still ride thru. Not the case, tunnel entrance was gated and locked - disappointing. The trail itself had some pretty scenery but is not well maintained or mowed.

Jane Addams Trail

just watch out for truck and trailers

September, 2020 by d.deyo2

Was on the trail up by Orangeville, a truck with a car trailer pulled off of 26 onto the trail . Not sure how he made the 2 bridge but wasn’t their when we made it back . Bring the bug spray sometimes Their terrible and sometimes their not ! Otherwise a nice trail to Freeport. Went to the pecatonica trail outside of Freeport over grown with grass. Not sure how far it was like that

Badger State Trail

The Stewart Tunnel is closed off because it is structurally unsafe. It is also posted on The Friends Of The Suagar and Badger State Trails Website.

September, 2020 by jacoblawrencegrabow

The Stewart Tunnel is closed off because it is structurally unsafe. It is also posted on The Friends Of The Suagar and Badger State Trails Website.

Badger State Trail

https://dnr.wisconsin.gov/topic/parks/badger For more current information see link to the WDNR website and Stewart Tunnel will likely not be open for the remainder of 2020.

September, 2020 by jacoblawrencegrabow

https://dnr.wisconsin.gov/topic/parks/badger For more current information see link to the WDNR website and Stewart Tunnel will likely not be open for the remainder of 2020.

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