Find the top rated trails in Freeport, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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...
This is a newly constructed path that runs between S. Main Street and the Rock River in Rockford. It was built as part of the re-building of S. Main Street and runs from South Park south to the...
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 Rock Valley College Path is a paved route looping around and through its namesake campus in Rockford. At its southern end, it connects to the Spring Brook Road bike lanes that continue east to the...
The Harlem Township Bike Path lies not far from the Rock River in western Machesney Park in the Rockford metropolitan area. The trail consists of a lower (southwest) and an upper (northeast) loop in...
Baumann Park is adjacent to the Kishwaukee River in Cherry Valley, a community on the outskirts of Rockford in northern Illinois. A paved pathway runs through the park and loops around Baumann Park...
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...
This path runs along the west side of the North Alpine Road in the Village of Machesney Park. It starts at the Schnuks parking lot and stretches about a mile north to the Lowe’s store parking area....
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 Cannonball Path runs on a railbanked Union Pacific corridor from near downtown Madison to Fitchburg, a southern suburb. A majority of the paved trail is complete between Madison's...
Oregon Park East Bike Path is nestled along the east bank of the Rock River in the small town of Oregon in northern Illinois. The 23-acre park offers athletic facilities, restrooms, grills, and picnic...
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The Sterling Multi-Activity Recreational Trail starts at one end at the edge of the Hoover Park parking lot and heads into a scenic wooded trail crossing a wooden bridge over Woodlawn Creek and...
This path runs along the north side of Highway 11 and south of the city of Janesville. The eastern end starts about 3/4 of a mile west of I-39 and runs all the way to S County Road D, crossing over...
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...
Janesville's Spring Brook Trail provides an important non-motorized route to many of the city's popular recreational amenities. The pathway begins just off the eastern terminus of the Rock River...
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 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 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...
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...
Located in the scenic riverside city of Clinton, the Clinton Discovery Trail offers trail users a wonderful way to make the most of the city's prime location on the banks of the Mississippi River....
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...
This path runs along the north side of Highway 11 and south of the city of Janesville. The eastern end starts about 3/4 of a mile west of I-39 and runs all the way to S County Road D, crossing over...
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...
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 Kiwanis Bike Trail, named for the Kiwanis Club that spearheaded the effort to build the trail, parallels the western bank of the Rock River through the southern Wisconsin community of Janesville....
This is a newly constructed path that runs between S. Main Street and the Rock River in Rockford. It was built as part of the re-building of S. Main Street and runs from South Park south to the...
The Dorr Road Bike Path begins at South Beloit Municipal Park and parallels the roadway for its entire length. The views are primarily residential. After about three-quarters of a mile (from the...
In the Village of Roscoe, a paved path of just over a mile parallels Main Street (which becomes Frontage Road) and then continues along the south side of McDonald Road, a quiet residential street....
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...
Stretching from Afton to Janesville, the northern section of the Peace Trail offers a paved, tree-shaded route paralleling the Rock River and an active rail line. At its northern end, the trail merges...
This path runs along the west side of the North Alpine Road in the Village of Machesney Park. It starts at the Schnuks parking lot and stretches about a mile north to the Lowe’s store parking area....
The Mel Anderson Memorial Path, named for a long-serving alderman of the Seventh Ward, stretches nearly 3 miles, connecting Lockwood Park, Searls Park, Bressler Park and Talcott-Page Park. Mid-way,...
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 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 Williamson Parkway Bike Path offers a pleasant, paved route through a residential area in southern Rockton. The mile-long trail follows its namesake roadway from Freeport Road (also known as S....
The paved trail running through Nick Saelens Memorial Park is a pretty one, with a loop around a small pond and much of it following a tree-lined creek. The park is nestled in the Village of Durand in...
The Bauer Memorial Path provides a short route through residential and commercial areas of Machesney Park, a northern suburb of Rockford. The trail begins at the Harlem Community Center and travels in...
Oregon Park East Bike Path is nestled along the east bank of the Rock River in the small town of Oregon in northern Illinois. The 23-acre park offers athletic facilities, restrooms, grills, and picnic...
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 Harlem Township Bike Path lies not far from the Rock River in western Machesney Park in the Rockford metropolitan area. The trail consists of a lower (southwest) and an upper (northeast) loop in...
The Charles Street Community Path offers a neighborhood route through southeastern Rockford, connecting residents to CherryVale Mall on its eastern end. On its western end, Alpine Park is just north...
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 Willow Creek Path is a pleasant, tree-lined trail that follows its namesake creek for most of its journey through the communities of Machesney Park and Loves Park in the Rockford metropolitan...
This path runs along the north side of Highway 11 and south of the city of Janesville. The eastern end starts about 3/4 of a mile west of I-39 and runs all the way to S County Road D, crossing over...
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...
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...
Located in the scenic riverside city of Clinton, the Clinton Discovery Trail offers trail users a wonderful way to make the most of the city's prime location on the banks of the Mississippi River....
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....
Although a relatively short trail, the Leland Path provides an important connection between the Hononegah Recreation Path and the Stone Bridge Trail. The pleasant, tree-dotted pathway travels through...
The Sterling Multi-Activity Recreational Trail starts at one end at the edge of the Hoover Park parking lot and heads into a scenic wooded trail crossing a wooden bridge over Woodlawn Creek and...
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 Riverfront Path winds nearly 7 miles through downtown Belvidere, east of Rockford in northern Illinois. As its name implies, the paved scenic trail follows the waterway for most of its...
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 Four Sisters Bike Path forms a horseshoe around the northern end of Rochelle, a small city south of Rockford in northern Illinois. The path connects several schools and parks, and the city has...
The Bauer Memorial Path provides a short route through residential and commercial areas of Machesney Park, a northern suburb of Rockford. The trail begins at the Harlem Community Center and travels in...
The Galena River Trail is built upon an old railroad spur of the Burlington Railroad main line, constructed in 1886. The spur linked Galena to Galena Junction, where the main railroad linestill...
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....
This is a newly constructed path that runs between S. Main Street and the Rock River in Rockford. It was built as part of the re-building of S. Main Street and runs from South Park south to the...
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 Cannonball Path runs on a railbanked Union Pacific corridor from near downtown Madison to Fitchburg, a southern suburb. A majority of the paved trail is complete between Madison's...
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.
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