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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We ride trails. We love trails. No pavement required. We embrace the crushed surface. We love to bike. The Omaha trail is surrounded by beautiful scenery. It begins and ends in friendly towns. It was strewn with debris the day after a storm, yet we were undeterred. You can bike around debris. Sadly, you can’t miss the ridges, ruts and roughness of a once paved trail. Omaha stole our energy and joy of riding. We rode on because we don’t quit. But it wasn’t enjoyable and was only memorable for the relief of finishing and knowing we won’t ride Omaha again. It’s unfortunate. The 400 is nearby. It is a far better choice, as is just about any other trail.
The trail is well maintained and an easy ride. It follows the terrain. The views are beautiful. Lots of families either walking or biking.
I rode the Duncan Creek trail in early June 2025. It was very enjoyable. I wasn’t watching my map closely and I ended up on the Old Abe trail that connects to it. Overall really good 5 star trail. Traveling cyclist Facebook
Since the tornado in May 2025 there is two miles of trees down not far from Juneau. It is impassable. I rerouted from prospect onto Hwy 26 to Swan Rd.
I enjoyed the south half but the part through the city was not well or marked at all. Route would be vastly improved with some signage.
Rode the trail the last couple days, loved it. It’s in great shape and is pretty flat. Happened to be there when the Wheelmen were riding with the high wheels!
I rode the entire trail from Seymour to New London and back in early June 2025. The trail is in super good shape and rideable with a road bike. There was a tree down across the trail about a mile west of Shiocton but easy to maneuver around. A really nice quiet ride in the countryside with no death machines. I rate it five stars. Traveling cyclist Facebook
We’ve done this trail twice and really enjoy it. Was attending a conference in SP and decided to bring bikes along. Weather was perfect for riding so we took advantage and rode this trail. It was wonderful. Love the variety of ‘environments’ you bike through, especially Schmeekle Reserve. The train is well maintained. Only delay was waiting on a train for 45 minutes!!
I rode the length of this trail from Phoenix Park in Eau Claire to the endpoint in Durand and back in early June 2025. The trail was closed at Owen park but it was easy to get around it. Further down the trail there was a sign that about a mile or two of trail was to be closed from 6-9-25 to 7-2-25 which was after I was on it. At about 11 miles just north of Caryville the blacktop surface deteriorates and the trail becomes more adventurous. Just SW of Meridean the trail is closed for an impassable short flooded section. Traveling cyclist Facebook
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