Explore the best rated trails in Darlington, WI, whether you're looking for an easy walking trail or a bike trail like the Capital City State Trail and Cannonball Path . With more than 47 trails covering 415 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
Sept. 27, 2025 / Incredibly wonderful temps inspired us to make the 1 1/4 hr. Drive to Sauk City for one of our favorite trails. We started at the southern end and rode the length to the trail head near Devils Lake State park. While the trail would really be enhanced if it would end within the state park, my wife and I find it a wonderful ride. Interesting mile markers, lots of areas with benches for rest stops, beautiful scenery along the way; and the trail has been always maintained to perfection.
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.
9/13/25 We began at the east end of the Lower Yahara Trail and then picked up the City Trail from there. Both trails were in exceptional condition. Traffic was busy, however the weather in mid-September in the low 80's certainly brought people out. A very friendly trail by anyone's standards. Well worth the 50 minute drive to get here. This is the second September we've rode this trail.
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.
Really nice trail but walker be careful. So many rude riders not letting you know they are coming behind you. 3 simple words “on your left”. When riding I always give walkers and other riders plenty of warning when passing, plus always slowing down.
(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..
Rode this trail end-to-end yesterday. The asphalt is in like-new condition and the scenery is beautiful. While we greatly prefer shaded trails in the hot summer, the lengthy stretches of sun on this trail were tolerable due to temps in the high 70’s and a light breeze. Can’t wait to ride this again in the fall. I’m sure the autumn colors near the northern half will be spectacular.
Rode out 6+ miles from the south end. Apparently they are going to build a bridge across the river sometime soon..Noticed a sign along the trail, that stated you need a permit to ride the trail?! Nice along the river, then out into open fields.
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.
We rode from Albany to Fulton. There’s minimal signage along the way so we stopped a lot to check our app. Not great trail along the way. Will skip this portion as a repeat ride.
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