Find the top rated cross country skiing trails in Freeport, 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.
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...
The Kishwaukee River Recreation Path runs for 2.5 miles in Cherry Valley on the outskirts of Rockford in northern Illinois. The well-maintained, asphalt trail connects the Kishwaukee River Forest...
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...
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...
The Pecatonica Prairie Trail, formerly known as the Pecatonica Prairie Path, is a 12.5-mile rail-trail extending from the western edge of Rockford to the Winnebago–Stephenson county line west of...
The Great River Trail is a breathtaking journey along more than 60 miles of the Mississippi River in northern Illinois. In places, the paved trail follows the former spur route of the Chicago, St....
The Stone Mill Trail runs between Lawrence Road in Harvard and Maxon Road in Chemung. The 1.5-mile, paved trail mostly parallels County Highway 17 (Ramer Road) and active railroad tracks, and will...
The Bear River Recreation Trail follows part of the Maquoketa River outside of Spragueville and Preston, through bucolic countryside of woodlands, farms and river lowlands. You can start the trail in...
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...
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...
The Long Prairie Trail journeys across the width of agricultural Boone County for nearly 14 miles on the railroad corridor previously used by the Kenosha and Rockford Railroad, later known as the...
The Copper Creek Trail runs for a short distance from the town of Preston, heading northwest along Copper Creek to meet with the Bear River Recreation Trail. You'll find a nice picnic spot with a...
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...
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...
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...
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...
The trail user can be transported from the bustling Westwood Fitness and Sports Center to a beautiful wooded trail that offers Elkhorn Creek on the far outer loop of the trail, a shelter at the top of...
The paved Rock River Recreation Trail winds throughout downtown Rockford and environs, following the east bank of the Rock River through Shorewood Park and Martin Memorial Park. Officially, the trail...
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...
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...
The Long Prairie Trail journeys across the width of agricultural Boone County for nearly 14 miles on the railroad corridor previously used by the Kenosha and Rockford Railroad, later known as the...
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...
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...
The trail user can be transported from the bustling Westwood Fitness and Sports Center to a beautiful wooded trail that offers Elkhorn Creek on the far outer loop of the trail, a shelter at the top of...
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...
The Stone Mill Trail runs between Lawrence Road in Harvard and Maxon Road in Chemung. The 1.5-mile, paved trail mostly parallels County Highway 17 (Ramer Road) and active railroad tracks, and will...
The Bear River Recreation Trail follows part of the Maquoketa River outside of Spragueville and Preston, through bucolic countryside of woodlands, farms and river lowlands. You can start the trail in...
The Pecatonica Prairie Trail, formerly known as the Pecatonica Prairie Path, is a 12.5-mile rail-trail extending from the western edge of Rockford to the Winnebago–Stephenson county line west of...
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...
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...
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...
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...
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...
The Kishwaukee River Recreation Path runs for 2.5 miles in Cherry Valley on the outskirts of Rockford in northern Illinois. The well-maintained, asphalt trail connects the Kishwaukee River Forest...
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...
The paved Rock River Recreation Trail winds throughout downtown Rockford and environs, following the east bank of the Rock River through Shorewood Park and Martin Memorial Park. Officially, the trail...
The Copper Creek Trail runs for a short distance from the town of Preston, heading northwest along Copper Creek to meet with the Bear River Recreation Trail. You'll find a nice picnic spot with a...
The Great River Trail is a breathtaking journey along more than 60 miles of the Mississippi River in northern Illinois. In places, the paved trail follows the former spur route of the Chicago, St....
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...
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...
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...
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...
The Kishwaukee River Recreation Path runs for 2.5 miles in Cherry Valley on the outskirts of Rockford in northern Illinois. The well-maintained, asphalt trail connects the Kishwaukee River Forest...
The Pecatonica Prairie Trail, formerly known as the Pecatonica Prairie Path, is a 12.5-mile rail-trail extending from the western edge of Rockford to the Winnebago–Stephenson county line west of...
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...
The Bear River Recreation Trail follows part of the Maquoketa River outside of Spragueville and Preston, through bucolic countryside of woodlands, farms and river lowlands. You can start the trail in...
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...
The Copper Creek Trail runs for a short distance from the town of Preston, heading northwest along Copper Creek to meet with the Bear River Recreation Trail. You'll find a nice picnic spot with a...
The paved Rock River Recreation Trail winds throughout downtown Rockford and environs, following the east bank of the Rock River through Shorewood Park and Martin Memorial Park. Officially, the trail...
The Great River Trail is a breathtaking journey along more than 60 miles of the Mississippi River in northern Illinois. In places, the paved trail follows the former spur route of the Chicago, St....
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...
The trail user can be transported from the bustling Westwood Fitness and Sports Center to a beautiful wooded trail that offers Elkhorn Creek on the far outer loop of the trail, a shelter at the top of...
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...
The Long Prairie Trail journeys across the width of agricultural Boone County for nearly 14 miles on the railroad corridor previously used by the Kenosha and Rockford Railroad, later known as the...
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...
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...
The Stone Mill Trail runs between Lawrence Road in Harvard and Maxon Road in Chemung. The 1.5-mile, paved trail mostly parallels County Highway 17 (Ramer Road) and active railroad tracks, and will...
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...
we love the trail and we will be going this weekend
This trail has so much potential. That's what really makes it disappointing. The eastern portion spent much of this summer being used by the electric utility, so it was technically closed. I rode it a few times in the evenings, but it definitely required a mountain bike. West of Welden Road it returned to the regular trail. Overall it's okay with a few soft spots. You definitely don't want to ride it if there's been rain recently. There are quite a few places that don't drain very well. I prefer my mountain bike over my commuter, even though my commuter has 38c tires. I enjoy riding it for a change of pace, but I'm sure I couldn't get my wife to ride it with me.
Beautiful summer day for a ride. Started in Freeport at the trailhead using city streets to get to heart of trail north of town. Easy ride and not to far. Good parking facilities in town. Freeport's a great town. Path is fairly well maintained with a few bumps along the way. Nothing to slow me down. Quiet countryside for the most part, farms fields and the occasional county road/highway crossing. Foliage was in full bloom with all the rainy/hot weather recently. Highly recommend.
In September 2018 a friend and I biked the trail from Orangeville to Freeport and back. Signage on the trail is good. It appears to be lightly used, as we stopped frequently to clear away fallen trees and tree limbs blocking the trail. A pair of sandhill cranes was in a field just south of Orangeville. Walnuts on the trail were a challenge as hard to see in the leaves. The trail is wide enough to ride two abreast. Black flies at Tutty's Landing were a problem, so we hurried into Freeport for great coffee at 9 East. Recommend the BP convenience store in Orangeville for lunch or a snack. Bathrooms at the Orangeville parking area and Tutty's Landing.
There’s the official path. While nice and paved, also has nice locally known paths. If you have a dirt/gravel capable bike, seek out the more challenging side trails. They are marked at the trailheads but the signage is hidden behind tall grasses and trees. Parts of the trails are visible via Google Maps Satellite view. Pro tip: bring mosquito repellent.
There are some rough spots on this trail! Also, just north of Albany is a section of gravel road to travel. I don’t know how long it is bc I don’t take my road bike on gravel or fresh chip seal.
This could be a sweet trail if someone actually cut the weeds. The only thing in good repair on several trails in this area of WI. are the drop- box's for your $5.00 dollar a day, per person, fee. We spent over a thousand dollars in the area on motels, food , gas, fee's etc. The experience, while still fun, could have been so much more. Pa. Tandem Team, (72 and 69 yrs. of age)
Stayed at the Thomson Causeway Campground and rented bikes from Arnold's Bikes in Thomson (highly recommended). The ride north to Savanna was beautiful as was the ride down south to see the Fulton Dutch windmill. Good diversity of fields, tree lined runs, and a general feeling of peacefulness not found near Chicago.
Only gripes were where there were stretches of bike path that had: sketchy amounts of wood debris, lack of signage when zizagging onto local roads, and deteriorating surfaces that made for a very uncomfortable ride on road bike tires (23-25mm).
The pros:
Tons of wild flowers and butterflies all along the way
The cons:
We have ridden dozens of rail-trails on our recumbent tandem. This one has a fair (at best) limestone surface. The center of the trail is overgrown, so you are restricted to about a one foot wide lane in either direction. There are some nasty holes at random locations. Soft spots in the surface here and there that are very difficult on hybrid size tires. Vegetation hanging out across the trail in spots. All this makes it difficult to enjoy the ride, because you need to concentrate on the trail so much.
I would not recommend this one for any less than mountain bike size tires.
Both Winnebago and Pecatonica are the typical lovely small Illinois farm towns with shops and restaurants in both. We chose to start in Winnebago (just off route 20) and use one of the many fast-food parking lots. There is a trail from there to downtown, where you pick up the main trail.
I really like this trail and have ridden it now several times with both a road bike and a light hybrid. Pros: long, paved, scenic, uncrowded. Beautiful farmland and wildflowers, lots of trees for a shady ride on a hot day, wildlife and peaceful views. Stretches of the trail that are in great shape and a few key rest areas and comfort stations along the route. Excellent diner (Boone Co. Family Restaurant) right off the trail in Caledonia. Nicest long section is west of Caledonia. Cons: many parts of this trail are bad to downright treacherous, especially near bridges. You could easily catch your tire in a center crack while trying to avoid a pothole on your side of the trail. No mile or distance markers. Shady trail means debris is damp after a rain, and sketchy for road bikes. Some horrible bridge transitions. Trail is out east of Capron at the moment. Recommendations: Could be fabulous if better maintained. In current condition, better for a hybrid. OK for a road bike on a dry day. Either way, wear a helmet.
We rode from the first trailhead in Rock Island to Cordova. About 25 miles one way. We all loved the trail. It was a mix of urban, small town and rural. I especially liked riding the top of the levy right next to the river. However the trail is very bumpy in spots. It could use some work. All four of us were on road bikes and the trail is fine for road bikes but the bumps got old. On the way out it didn’t really bother me but once we turned around and were getting tired the constant bumps got old quickly. One thing we liked was that you rarely had to cross a road.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Map Search
