Middleton, WI Cross Country Skiing Trails and Maps

386 Reviews

Looking for the best Cross Country Skiing trails around Middleton?

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

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Activities
Length
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16 Results
Activities
Length
Surfaces
Type

400 State Trail

22.3 mi
State: WI
Crushed Stone

Badger State Trail

40 mi
State: WI
Asphalt, Crushed Stone

Cheese Country Recreation Trail

47 mi
State: WI
Crushed Stone, Gravel

Glacial Drumlin State Trail

52 mi
State: WI
Asphalt, Crushed Stone, Gravel

Glacial River Trail

55.8 mi
State: WI
Asphalt, Crushed Stone

Jane Addams Trail

18.9 mi
State: IL
Asphalt, Crushed Stone

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

Rock River Parkway Trail

2.4 mi
State: WI
Asphalt, Concrete

Southwest Commuter Path

5.6 mi
State: WI
Asphalt

Starkweather Creek Path

3.1 mi
State: WI
Asphalt

Sugar River State Trail

22.7 mi
State: WI
Asphalt, Crushed Stone

Wild Goose State Trail

34.4 mi
State: WI
Asphalt, Crushed Stone, Dirt, Grass

Wingra Creek Path

1.9 mi
State: WI
Asphalt

Wolf Run Trail (WI)

2 mi
State: WI
Crushed Stone
Trail Image Trail Name States Length Surface Rating
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 and St....
WI 22.3 mi Crushed Stone
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 52-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 52 mi Asphalt, Crushed Stone, Gravel
The Glacial River Trail provides bikers, pedestrians, and in-line skaters with a 55.8-mile off-road/on-road rural route winding through farmland, prairie, wetlands, and woodlands as it passes through...
WI 55.8 mi Asphalt, Crushed Stone
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 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 Rock River Parkway Trail in Janesville runs between Rockport Park and S. Jackson Street bridge on the north side of the river. Here, at the trail's eastern terminus, you can easily link to Spring...
WI 2.4 mi Asphalt, Concrete
All it takes is a short ride on Madison’s 5.6-mile South  west Commuter Path to understand the critical role it plays in getting people around town. Not only does it pass within a mile of the State...
WI 5.6 mi Asphalt
The Starkweather Creek Path traces the waterway north from the Capital City State Trail through Madison’s eastern neighborhoods of Starkweather, Worthington Park, Eken Park and Carpenter-Ridgeway. The...
WI 3.1 mi Asphalt
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
The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...
WI 34.4 mi Asphalt, Crushed Stone, Dirt, Grass
The Wingra Creek Path—also known as the Wingra Bike Path—runs along the winding waterway in Madison. The trail provides a critical link from the neighborhoods south of downtown Madison to the Capital...
WI 1.9 mi Asphalt
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

Now, More Than Ever, Trails Matter!

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Trails by activity

Glacial River Trail

WI - 55.8 miles

The Glacial River Trail provides bikers, pedestrians, and in-line skaters with a 55.8-mile off-road/on-road rural route winding through farmland, prairie, wetlands, and woodlands as it passes through...

400 State Trail

WI - 22.3 miles

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 and St....

Wolf Run Trail (WI)

WI - 2 miles

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...

Wild Goose State Trail

WI - 34.4 miles

The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...

Accordion

Rock River Parkway Trail

WI - 2.4 miles

The Rock River Parkway Trail in Janesville runs between Rockport Park and S. Jackson Street bridge on the north side of the river. Here, at the trail's eastern terminus, you can easily link to Spring...

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...

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...

Starkweather Creek Path

WI - 3.1 miles

The Starkweather Creek Path traces the waterway north from the Capital City State Trail through Madison’s eastern neighborhoods of Starkweather, Worthington Park, Eken Park and Carpenter-Ridgeway. 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...

Glacial Drumlin State Trail

WI - 52 miles

The 52-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...

Wingra Creek Path

WI - 1.9 miles

The Wingra Creek Path—also known as the Wingra Bike Path—runs along the winding waterway in Madison. The trail provides a critical link from the neighborhoods south of downtown Madison to the Capital...

Southwest Commuter Path

WI - 5.6 miles

All it takes is a short ride on Madison’s 5.6-mile South  west Commuter Path to understand the critical role it plays in getting people around town. Not only does it pass within a mile of the State...

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...

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...

Starkweather Creek Path

WI - 3.1 miles

The Starkweather Creek Path traces the waterway north from the Capital City State Trail through Madison’s eastern neighborhoods of Starkweather, Worthington Park, Eken Park and Carpenter-Ridgeway. The...

Accordion

Glacial River Trail

WI - 55.8 miles

The Glacial River Trail provides bikers, pedestrians, and in-line skaters with a 55.8-mile off-road/on-road rural route winding through farmland, prairie, wetlands, and woodlands as it passes through...

Wild Goose State Trail

WI - 34.4 miles

The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...

400 State Trail

WI - 22.3 miles

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 and St....

Southwest Commuter Path

WI - 5.6 miles

All it takes is a short ride on Madison’s 5.6-mile South  west Commuter Path to understand the critical role it plays in getting people around town. Not only does it pass within a mile of the State...

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...

Wingra Creek Path

WI - 1.9 miles

The Wingra Creek Path—also known as the Wingra Bike Path—runs along the winding waterway in Madison. The trail provides a critical link from the neighborhoods south of downtown Madison to the Capital...

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...

Wolf Run Trail (WI)

WI - 2 miles

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...

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...

Rock River Parkway Trail

WI - 2.4 miles

The Rock River Parkway Trail in Janesville runs between Rockport Park and S. Jackson Street bridge on the north side of the river. Here, at the trail's eastern terminus, you can easily link to Spring...

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...

Glacial Drumlin State Trail

WI - 52 miles

The 52-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...

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...

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...

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...

Starkweather Creek Path

WI - 3.1 miles

The Starkweather Creek Path traces the waterway north from the Capital City State Trail through Madison’s eastern neighborhoods of Starkweather, Worthington Park, Eken Park and Carpenter-Ridgeway. The...

Accordion

Glacial River Trail

WI - 55.8 miles

The Glacial River Trail provides bikers, pedestrians, and in-line skaters with a 55.8-mile off-road/on-road rural route winding through farmland, prairie, wetlands, and woodlands as it passes through...

Glacial Drumlin State Trail

WI - 52 miles

The 52-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...

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...

400 State Trail

WI - 22.3 miles

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 and St....

Wild Goose State Trail

WI - 34.4 miles

The Wild Goose State Trail is a premier rail-trail, spanning approximately 35 miles in Dodge and Fond du Lac counties. If you are looking for a peaceful and beautiful place to visit, this trail has it...

Wolf Run Trail (WI)

WI - 2 miles

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...

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...

Rock River Parkway Trail

WI - 2.4 miles

The Rock River Parkway Trail in Janesville runs between Rockport Park and S. Jackson Street bridge on the north side of the river. Here, at the trail's eastern terminus, you can easily link to Spring...

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...

Wingra Creek Path

WI - 1.9 miles

The Wingra Creek Path—also known as the Wingra Bike Path—runs along the winding waterway in Madison. The trail provides a critical link from the neighborhoods south of downtown Madison to the Capital...

Southwest Commuter Path

WI - 5.6 miles

All it takes is a short ride on Madison’s 5.6-mile South  west Commuter Path to understand the critical role it plays in getting people around town. Not only does it pass within a mile of the State...

Recent Trail Reviews

Great Sauk State Trail

Good trail

September, 2021 by 5svcy8m2tv

From VFW parking lot to the end (fenced off area that might one day head into Devils Lake) is just under 10M. Mild grades, fully paved and lots of areas to stop and site see. This trail goes into the Badger Lands which used to be a 10,000 acre munitions plant during WWII. Now the area is split into USDA, public space, and Ho Chunk Nation territory (private). Very well maintained trail with minimal interruptions.

Glacial Drumlin State Trail

Lake Mills to Deerfield

September, 2021 by juliecat320

Beautiful trail between Lake Mills and Deerfield. Ice cream in Deerfield! No ruts - hard packed crushed limestone. I rode my road bike with out problem. Just wish they had ice

South Fork Trail (WI)

nice trail but difficult-very hilly

September, 2021 by lauraparman

This trail is short but riding from Middleton to Pleasant View is mostly uphill! Tough for recreational bikers. But pretty ride.

Accordion

Glacial Drumlin State Trail

Ok but not a lot of features

September, 2021 by gmeister50

I started at the trail head in Cottage Grove. Paid my $5 and took off east. The path is mostly crushed lime stone and nice riding. It has slight grades but no hills. The trail is mostly straight and flat which is why I say it lacks features. Yes I know it is a converted train tracks. Lots of farms and fields with flowers. (features?) Also tree lined. It goes by many small towns along the way but they looked deserted. Didn't see many people.
I think riding the IPP and Fox River trail is better.

Cheese Country Recreation Trail

Went 20+ miles without seeing a sole, great trails, little rough in spots. One washout we barely missed that would have put you deep into your seatbelts

September, 2021 by jimlauriebalzer

Went 20+ miles without seeing a sole, great trails, little rough in spots. One washout we barely missed that would have put you deep into your seatbelts

Sugar River State Trail

Sugar River Bike Trail

August, 2021 by sjfontherun

Such a terrible disappointment! Shame on the Wisconsin Department of resources for not maintaining this trail! We biked this trail about 20+ years ago with our children and it was wonderful. We started in Brodhead and we biked to Monticello and back to Brodhead. Yesterday my husband and I started in New Glarus and we biked to Albany and back to New Glarus. The only highlight was breakfast at the M&M Café in Monticello. This cafe has not changed in 20 some years💕.
I honestly don’t think there has been any crushed lime stone put down in that trail since we biked it last. Why is the department of natural resources not maintaining this trail? You have an absolute gold mind here, please realize it’s a value and put some time into it. Cut the grass on both sides of the trail, put down new lime stone!
The Chalet Landhaus is a wonderful place to stay a New Glarus, it is right on the trail.

Glacial River Trail

north branch Glacial River Trail

August, 2021 by mem9622

We absolutely loved this trail. We started near the airport in Watertown Wisconsin and took the back roads all the way to the end of the marked trail. There’s a small 2 mile segment that’s a long state route 16 but it’s a dedicated trail on the side of that road. Loud traffic but just a small section so not that bad of a deal. Everything else is beautiful country roads very little traffic absolutely wonderful rolling Hhills and farmland. It took us three hours round-trip very leisurely pace of 9 mph Be sure to eat at the Main Street diner in Watertown

Jane Addams Trail

Another great ride...

August, 2021 by bazjkm2

Just hit the trail today from Tutty's Crossing in Freeport all the way to Wisconsin state line (35 miles round trip). It's been 3 years this month since my last ride there. It's in great shape and the weather was perfect. Great scenery for small towns and farmland. Plenty of food, drink and shopping in Freeport. (Definitely check out Union Dairy at Douglas and Adams!)

5 star trail for any serious biker.

400 State Trail

This is our new favorite

August, 2021 by emmettbrown

We did an 10.5 mile stretch from Elroy, WI to about 3 miles south of Wonewoc. Round trip 21 miles. We intended to do 30 miles but we're getting older and the air quality was terrible due to fires in Canada. That said this is a beautiful trail, very scenic, smooth, and a pretty flat easy ride. At a few of the road crossings the ends of the trail were filled in with sand instead of gravel, so watch out so you don't lose control. We chose the 400 due to having lots of stops with bathrooms. We were not disappointed. All of the facilities are clean and well maintained. Most of the small towns along the way have food and beer available, and the local folks are very welcoming and proud of their association with the trail. This has become our favorite WI trail. We hope to get back out there next year and finish the trail.

Military Ridge State Trail

Blue Mound to Dodgeville

July, 2021 by drprovanch

We camped at Blue Mound State Park and biked the first day to Dodgeville. The camp is at mile marker 22, so 36 miles round trip. Great scenery as the elevation is high: distant farmlands, golf courses, forest,…. The trail is in great condition, winding and rolling throughout farmlands, wooded area, prairies, and small rural communities. Our return trip was in misting rain and the forecast for storms later that week canceled our plans for the eastern leg until another time.

Sugar River State Trail

Brodhead to Albany July 2021

July, 2021 by john701

First time on the trail. I had a mountain bike, which was appropriate. Trail was mostly two 8-10 inch bare patches with grasses/weeds between. Otherwise, it was fine. Covered bridge was a surprise.

Great Sauk State Trail

Beautiful ride!

July, 2021 by acarr6496

The prairie restoration is simply beautiful!! Many wildflowers were in bloom. This is a wonderful ride and highly recommend.

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