Find the top rated dog walking trails in Winnebago, whether you're looking for an easy short dog walking trail or a long dog walking trail, you'll find what you're looking for. Click on a dog walking trail below to find trail descriptions, trail maps, photos, and reviews.
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This trail starts behind my home in sycamore. I’ve ridden it dozens of times. I like to stop at the winners circle at the speedway and grab lunch. Flat and well maintained.
This is a short path off the north end of the Kishwaukee-Kiwanis Trail. It was freshly repaved for a smooth ride with nice greenery on each side and a bridge over the river near the northwest end. The path is handicapped accessible and there was no traffic on the neighborhood cross streets. I didn't linger, but based on the number of squirrels crossing the path, I could imagine seeing a fair amount of wildlife at the right time of day.
Started this trail at the east end (Floyd Tilton Park). The trail is asphalt and in good condition. On the east side, the ride parallels the small Kyte River. As others have mentioned, you pass under the busier roads, which is nice. The trail swings around the high school, then south along 20th Street. There is an extension that heads west from Squire Landings, cutting through cornfields and then paralleling the RR tracks. I did an out-and-back on this section, then rode back to the starting point along 10th Ave. Traffic was low on a Saturday afternoon. After the ride, I went down to Rochelle Rail Park to absorb some local history and watch a couple of trains go by. I'd probably ride this trail more often if I lived closer.
Trail is in great shape. Nice smooth surface, hard packed , very tiny stones if any. Trail west of Burlington is maybe more scenic and goes through 2 small towns. Very flat so get to pedal the whole way. Lots of shade along the way. Found a good route to get through Burlington. Look up city bike routes on city website.
My son and I rode from the visitor center east to the first aqueduct, about 20 miles round trip. It was beautiful day, we took our time, looked for turtles and stopped at a Casey's in Wyanet for lunch. Keeping to a healthy diet I went for sausage pizza, Yoo-hoo and an iced sugar cookie. The trail was rough, and rougher in spots but not a problem on my gravel bike with 40 mm tires. My son rides a Synapse with 35 tires and did it have a problem. If you ride a road bike or prefer smooth trails this might not be for you. we enjoyed it.
Some really pretty parts but a lot of road riding. Started from Cattail Slough Boat Launch (free parking as long as you don’t have a boat trailer attached to your car), rode to Mississippi Pallisades State Park and camped. Rode back the next day. Campground was fantastic and Krumpets Bakery in Fulton should not be missed. The actual trail portions were nice and the Thomson Recreational Area was nice. In Northern Illinois you have to know that there’s going to be a lot of long distance straight sections but this was excessively so. Maybe 35% was trail and 65% road. Happy to say I’ve ridden it but won’t return.
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.
Our annual women’s biking trip did this ride on our 3rd day, a total of 36 miles round trip. Woodstock needs to have a marked bike route from the end of Ridgefield Trace into downtown Woodstock as there is a lot of traffic where the trail ends. Some spots on the trail have a lot of bumpy cracks, but overall was OK for what we needed to get from Crystal Lake to Woodstock. Downtown Woodstock is very cute with lots of shops & restaurants with a cute park/square & where Groundhog Day was filmed.
(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..
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