Middleton, WI Cross Country Skiing Trails and Maps

303 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

Glacial Drumlin State Trail

53.4 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

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
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 53.4 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
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

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Trails by activity

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...

Glacial Drumlin State Trail

WI - 53.4 miles

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...

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

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

Accordion

Glacial Drumlin State Trail

WI - 53.4 miles

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...

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...

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...

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...

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...

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...

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...

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 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...

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...

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...

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...

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...

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...

Accordion

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...

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...

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...

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...

Glacial Drumlin State Trail

WI - 53.4 miles

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...

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...

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...

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....

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...

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...

Recent Trail Reviews

Glacial River Trail

A Return to Finish the Trail

October, 2019 by buehler868

I returned on one of those great Midwestern fall days to complete the portion of the Glacial River Trail south of Jefferson. I found the few miles that were in-fact a former railroad. The rest of the trail is in the WI-26 freeway corridor or on rural roads and city streets, but the trail is all paved.
The city of Fort Atkinson is very attractive with trail amenities including public art. I again found that the TrailLink map was a necessity as the signage on the tail is sparse.
My only negative is there is no need to do the on-highway portion south of N Wright Rd unless you want to continue to the connection to the Spring Brook Trail that will take you into Janesville.
For an out and back trip consider places where you can use the parallel old WI-26 for a different landscape view.

Pelishek-Tiffany Nature Trail

Clinton-Allens Grove

October, 2019 by suziesmithuw

Plenty of space to park stock trailer in gravel lot on Lake Shore Rd Clinton. Cute little covered bridge in small park with picnic tables was the start of my mule ride. There were trash receptacles, handicap accessible restroom & a wood post hitching rail. Many "sponsored" rest spots with wooden benches, picnic tables & some had roofs along the flat trail. Trail bed is wide, flat & firm as small crushed gravel & grass base. Views of plant/tree farm & rural properties after brief bit of SE side of Clinton. Mileage markers. Several blacktop road crossings. Easy, well-groomed trail. Small gravel lot at east end with trail map on kiosk. For lunch at Boar's Nest Bar ride Hill St (right uphill), stay right on Clinton St, quick Left along west side of the Park 1 block to stop sign Cty X. Ride directly across Cty X then straight across grass to cable picket line.
I-43 runs parallel to trail. Loud traffic but distance kept equines from becoming unnerved 🙂 Met a jogger, a hiker with a leashed dog on trail & 2 bicyclists at covered bridge. All were respectful of equines.

Cheese Country Recreation Trail

Nice ride

October, 2019 by blown86fox

If you are looking to take it easy and just go for a nice ride this is it. Smooth and simple. Very well maintained.

Accordion

Glacial River Trail

Paved Trail Makes for a Nice Long Ride

September, 2019 by buehler868

The Glacial River Trail in the Rock River valley is untypical for Wisconsin state trails in that it is entirely paved and not a rail-to-trail. It has a great mix of segments in the WI-26 freeway corridor, city streets and rural roads, with some good grades. I did the north part of the trail from Jefferson to the junction with the Wild Goose State Trail. There are no services provided by the trail owner, but the trail is free to use. The signage for the trail-turns is minimal so the Trail-Link map downloaded on your smart phone is a must. I especially enjoyed my ride thru the river towns of Jefferson, Johnson Creek and Watertown, where I took the time to ride around the downtowns. I will come back someday to do the south portion.

Badger State Trail

Badger State needs attention

September, 2019 by novakdks

We got on the trail at Lacy Street in Verona/Fitchburg WI. The trail was paved and in great shape at that point. Cyclists were using it as a commuter trail and there were several people out walking and running. The trail turned into non-paved surface and that is where we dismounted to pay the fee of $5. Oh my, what can I say. The trail is NOT crushed limestone. At places it appeared to be an abandoned trail except for the path made by a bicycle tire. It was a muddy, sticky mess. I had checked ahead of time and found out the Stewart Tunnel was closed, which saved us back tracking since there wasn't a sign indicating the tunnel was closed. We detoured onto Tunnel Rd and took various paved roads into New Glarus. The best part of the trail was the Monroe WI segment. There was a detour off of the trail as we were coming into town. Very good signage directing us through the road construction area. There was a very nice trailhead with a drinking fountain and restrooms as you came into town from the north. We continued to the downtown area and decided to take a break and headed to the Dairy Queen by exiting the trail at 5th Street and riding to 8th Street. It was a challenge to cross the street but it was during lunch hour. As we headed out of Monroe there was an area of very loose gravel vs crushed limestone. An inexperienced rider might have wrecked. The rest of the trail was not maintained until it connected with the Jane Adams Trail. It was is good shape into Freeport IL.

Glacial Drumlin State Trail

Glacial Drumlin Trail

September, 2019 by harvecon14

Parked at Cottage Grove today and biked out 23 miles and then back to car. It was annoying that we both paid our 5 dollars and then visited the rest room. No toilet paper in mens or women's and both stalls in women's were smeared with feces. Nice surface on trail. Not enough benches. This trail would definitely not qualify as a national rail trail.

Glacial River Trail

Uninhabited but lovely

September, 2019 by wilsonae

I grabbed the trail north of Janesville on my road bike. Crossed the bridge over the highway and did about a mile on the county road before winding through a new housing development and finding the actual trail. It's in great shape, lots of gentle rolling hills and a couple of roundabouts but not a single person anywhere along the trail. I rode to Milton and most of the trail parallels the highway so it's loud on one side but beautiful and agricultural on the other side. I saw hawks and finches and no humans of any kind. It was pretty sweet. I only gave it 4 stars because of the highway driving . Otherwise it's a 5-star paved trail.

Sugar River State Trail

Needs some TLC

September, 2019 by dlk6771

Being from Brodhead I have many memories of taking bike rides on the trail. But today... not so much. Is our trail less important than others? It seems to be. It is in desperate need of work. Sections of the path are down to one tire path only. Numerous holes and a lot of over growth. It was pretty sad seeing it in such disrepair.

Military Ridge State Trail

Nice weekend ride

September, 2019 by izzyo58

My husband and I rode the Military Ridge Trail from Dodgeville to Fitchburg on Saturday of Labor day weekend. We connected the Military Ridge Trail to Cannonball path to Capital City Path and stayed overnight at the Wyndam Garden Madison Fitchburg (total of 45 miles) . We enjoyed the Great Dane Pub and Brewery that is within walking distance from the hotel. Then we rode the trail back to Dodgeville on Sunday. We stopped in Mt Horeb for lunch both days. There are several shops and resturants so it was a nice break to get something to eat and walk around a while. The Military Ridge Trail is nice with varied scenery between rolling farms, wooded areas and marshland. There are a few places where it runs along the highway but overall I thought it was a scenic trail. Most of the trail is in good condition for a hybrid bike but there are a couple sections where there is grass growing in the middle of the path. It didn't cause any problems, but wasn't a well maintained as the other sectins. Overall for a rail trail, I thought it was in good condition. The most scenic part is through the Blue Mound State Park area and the Quarry Ridge Recreation area just west of Fitchburg. The section of the Capital City Trail across Fitchburg is very pretty with lots of wildflowers, but is has a few hills.

Pelishek-Tiffany Nature Trail

Lovely Ride

August, 2019 by tjtropp

I have become fond of this trail for its natural surface and rural feel. Don’t try it with skinny tires since the ground can be soft in spots. Also great fun to encounter the occasional horses.

Cheese Country Recreation Trail

Definitely NOT for bicycles

August, 2019 by thiahov

This was a difficult trail for bike riding. I must say that ALL ATV riders we encountered were respectful. They all slowed down and gave us space. Won’t be doing this again unless with an ATV.

Sugar River State Trail

Dangerous

August, 2019 by tlmascherin

We rode the Sugar River round-trip the weekend of July 27-28, 2019. We are experienced riders and were on hybrid bikes. The trail was in very poor condition, with many ruts, potholes and even mole holes. On the return ride, I caught the side of a pothole, fell, and broke a bone in my hand. Not good. The trail is in serious need of maintenance.

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