Find the top rated horseback riding trails in Middleton, 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.
Good easy trail. Started in New Glarus and went foe about 2 miles.
Love this trail but rode today between Riley and Brigham County Park and found the trail to be in extremely rough shape on either side of Mt. Horeb. Lots of ruts, giant holes and loose sand. Slow your roll and pay attention to utility flags and sticks identifying some of the bigger holes. Stay safe!
We took this trail from the Wild Goose trail but had no idea we would be on so many roads. As you got closer to Watertown, you are also on the road. We personally try to avoid roads as much as possible so we didn’t like this part. We only went to Watertown from the North so I am not sure what the rest of the trail is like. The actual bike paths are great.
Storm last night, tree across trail at 5.25. I'm contacting dnr now
Not scenic by any means, but the quality of the trail is nice as of May 2026. 1/3 Asphalt, 1/3 Limestone, 1/3 Sand. I would say they fixed most problematic surface issues that any other review complained about but like any other track with multiple mediums, always be mindful for chipmunk holes and washout. The path from the park in Richland Center to the start of the main path is a little confusing because it’s not clearly marked, and you do go through a busy intersection so make sure to map it out if unfamiliar. Enjoy!
We prefer paved trails and the Great Sauk Trail is among the best we've ridden! Ride it again last Saturday and the trail has been extended on the NE end since last time we rode it. Take a detour and check out Thoelke Cemetery for a bit of history; sites dating back just after WI became a state in 1848! Great eats at Gym Bar in Sauk and outstanding mojitos on the deck at Queues Bar right along the river just south of the Hwy 60 bridge in Prairie du Sac!
Beautiful multi-use trail. It is the only trail open to ATV/UTV’s in Southern WI
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.
This is a really nice gravel trail that is basically flat for its entire length. It offers a really nice ride that can be enjoyed by riders of all skill levels.
On this is a trail, you'll have a chance to pass through a few towns and cross quite a few bridges, most of which will rattle your teeth due to their rugged surfaces. You can expect there to be a mix of trees and scrub along a lot of the trail with open areas reveal whole lot of Wisconsin farmland. The trail has several access points along its route, so you can pick a distance that works for you.
One of the nicer things experienced along the trail was a little cooler with ice water for you to enjoy as you leave the town of Reedsburg. It's just an example of cool people doing cool things.
I actually rode beyond the Elroy on up to Sparta, which I highly recommend if you're looking for a longer ride. I spent the night in a hotel then made it a round trip the next morning.
Other than that, this was a really nice ride.
We rode this stretch out and back on September 15, 2025. The trail is flat and in good shape except for the numerous bridges (10 or 12) which are in pretty bad shape. It’s obvious that a few repairs were recently attempted, but those amount to replacement of a few boards in each bridge. Some bridges are very long and all are super bumpy. If you have an older bike I’d suggest walking it across the longer bridges. Otherwise the scenery is nice and there’s great rest areas with flush toilets in LaValle, Wonewoc and Elroy.
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.
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