Find the top rated horseback riding trails in Wisconsin, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
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Pretty and peaceful. It’s paved in Phelps but turns to gravel not longer after. Shaded mostly. I’m sure the tamaracks are really pretty in Fall. The ice cream store in Phelps is open till mid Sept, awesome place to get ice cream n baked goods after your ride.
This is just a short trip from point beach down to two rivers but it’s a fun trail to run. Many small rolling hills and curves! We have e-bikes so not much of a work out but it sure is a fun trail. By far my favorite little trail this year!
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.
The trail is mostly beautiful. Almost all crushed gravel, which we didn’t expect. In some parts the gravel is thick and loose. The only asphalt is on county roads. the concrete, as expected, was on sidewalks in town. The boardwalks were fun but be careful if you are riding on 3 wheels. If I hadn’t just rode the Heart of Vilas and the Root River State Trails, which are as close to perfect as you can get in this region, I would’ve given the Green Circle a 5 star review.
Second long trip for me and the first trip that was mostly rail trail one quarter of which was the Elroy Sparta. Beautiful trail and the safety of being away from most automobile traffic made the trip way less stressful
Rode this trail on a perfect “biking weather” day! Trail is paved and well maintained. Parts are winding but fairly flat. Many shaded portions. Went across bridges. Stopped in Manitowish Waters at Dixie’s coffee shop - great place with excellent service. This trail is hard to beat!
If your doing a there and back deal start in Sheboygan, do all the uphill stuff and then coast back lol. This trail is ok for scenery, prolly really shines in Fall, quite a bit of hills. It does run along the highway the whole time, connecting Fondy and Sheboygan. Plenty of parking along the way.. bathroom at the Greenbush one. Parts of the trail are shotty between Plymouth and Sheboygan. Trail has no tree coverage but random covered spots to sit. Bike shop in Sheboygan Falls.
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 and taken care of. It’s a good ride there and back..about 13 miles. I’m sure beautiful in Fall. Love that I left right from my campsite at Long Lake.
The Tank Creek Bridge is out due to a fire in May, 2025. We detoured onto Highway 35 (almost 5 miles) then to County XX (about 6 miles) to reach Midway and the trail. XX starts out paved then gravel and old asphalt until you near Midway. The trail is gorgeous! Might need to come during fall foliage.
The trail is kind of rough, old asphalt with crushed stones? But the area it runs through is really nice. Good test for my new phone holder, it didn't fall out! It would be a keeper if it could be smoother.
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