Find the top rated bike trails in Winnebago, whether you're looking for an easy short bike trail or a long bike trail, you'll find what you're looking for. Click on a bike trail below to find trail descriptions, trail maps, photos, and reviews.
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Did a round trip from Dean Street to Sycamore and back. Trail surface is pretty good however there are a few washouts and gopher holes. You just have to be careful. True to a former railroad bed, it is flat except for a few bridges. No busy streets to cross. The elevation profile shows a gentle rise from each end to the middle.
Do not just ride the trail and go home. At the west end take a few minutes to ride through downtown Sycamore. It is a delightful town. Enjoy some of the classic old homes on South Somonuk Street.
Started in Brodhead, and rode to Monticello and back on Labor Day weekend. First mile is right down 3rd avenue, which is fairly wide and marked for bike traffic, and car traffic was slow, and passed with plenty of distance. The trail itself starts on the north end of Brodhead, and overall was pretty good, packed crushed stone / fine gravel. We had no issues with our hybrids. The trail was relatively flat and an easy ride. There is one spot where the trail takes some sharp turns around a country club, and leaves the former railbed. The trail was a little soft in this part, and the curves little iffy, but still totally manageable on our bikes. 6 miles to Albany with decent scenery and shade. Crossing Hwy 59 on the north end of Albany was a little intimidating, but drivers were courteous and stopped to let us cross. Next up - 9 miles from Albany to Monticello. The scenery between Albany & Monticello was wonderful as you're either travelling in a protected wildlife area or right next to the river. The bridges looked tired, but posed no issues. Overall, saw a fair number of other bikers, maybe 2 dozen over the course of 4 hours? So definitely nice and quiet. Flush toilets and water fountains in Monticello & Albany, Pit toilet and water fountain in Monticello. 32.5 miles round trip for this section. Would definitely return to this one, it would probably be fantastic for fall colors.
(8/13/2025) - Beautiful day for a ride on the Jane Addams. Trail was in very good condition and it was a smooth ride all the way from Tutty's Crossing in Freeport to the Wisconsin state line (Badger State Trail in WI). Everything was green and lush and the country side scenery was beautiful. The Addams people do a very fine job of maintaining their trail. One of my favorites to ride every year! Highly recommended. Of course, don't forget to stop at Union Dairy afterwards for some delicious ice cream. It's the best.
Just finished riding this trail over four days. They were in the middle of repaving a section which I thought was great but right along route 84 very scary and hazardous.. you either had to walk your bike through the grass, or take your chances on the highway. The trail is poorly marked when you have to take secondary roads to reconnect with the trail, especially when you’re heading towards Moline.. good places to stay very close to the trail and there is no problem finding any place to eat. I’ve ridden it once that will probably be my only time I will ride this trail..
My buddy and I rode the trail from Big Hill Park to downtown Janesville yesterday. What a great ride. About 60% of the trail is shaded. The blacktop three miles or so from Janesville is heavily cracked and rough but not too bad. The first 9mi it’s a very smooth trail. We’ll be doing this one again.
This trail was miserable to ride with a hybrid touring bike. It would be completely unusable on a road bike despite what the trail description may say. The gravel is so bumpy and the trail has been barely maintained. Not much of a surprise in hindsight given the fact that I saw zero other cyclists throughout an entire day riding on this trail. I would only ride this trail again with a fat tire. What is nice though is the trail is very remote and quiet.
I’ve been walking and cycling this trail for most of my life and it’s always a wonderful experience, such beautiful scenery along the river. It’s by far my favorite trail in the Chicagoland area.
Section between poplar grove and route 76 is getting worse by the day, the chipmunks are taking over and the sharp granite railroad balast is cutting into our tires. No money in illinois budget to repair bicycle trails, the only people enjoying the trail are on those motorized fat tire bikes.
Rode this a year or two ago, and although it was a bit rough, it was enjoyable. Now, not so much. The asphalt trail from the east trailhead to Capron has been replaced with "crushed stone". The crushed stone has baseball sized chunks of asphalt and rock mixed in with it, and 50% of the rest are chunks bigger than an inch across. Barely passable on a gravel bike, if you find the right rut on the path. No way a road bike is making it down this stretch. Once you get to Capron, it's back to asphalt for a short bit, then it changes to gravel / crushed limestone. Some of the bridge crossing can be bone jarring, but not overwhelming. It changes back to asphalt outside of Poplar Grove, and continues all the way through to Caledonia. Some potholes can be pretty harsh, but not terrible. At some point between Poplar Grove and Caledonia, it turns back to gravel for a stretch. Although not my favorite, this was done well enough for our gravel bikes. We usually do this trail either from the east trailhead to Caledonia, or Caledonia into Roscoe, as there's a rest stop & parking in Caledonia. If you park on the street in Capron, and skip the first 2 miles, you'll be a lot better off. Although there's no water / bathrooms in Capron, there's a Casey's just down the street from the trail.
When Tommy Tompson was the governor of Wisconsin the state trails were well taken care of, I like to pull a two wheel trailer to carry my tools , food, drinks and extra clothes, the trail surface needs to be mowed in many places, should be graded over with fresh limestone. sandy and washed out spots, this and most Wisconsin trails are no place for thin tire road bikes. They want you to pay to use the trails but do bare minimum and half assed maintenance. there are pit toilets at Albany and Monticello. Do not count on water spigots pack plenty to drink.
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