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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Nice trail crossing Hwy 20 is kind of a pain but south of that it is nice. It goes to Hwy KR which is a lot further than the map shows. You can even go to Petrified Springs by taking the pathway that runs parallel to Hwy 31.
Be aware. Signage not good 1st part of south end (where we began).
Trail Link map + GPS very helpful. Since signs are more in keeping w/ biking, than nose on phone, a suggestion: At decision points pls post signs, rather than down the road when you’ve luckily made a correct turn. Once through that the South end chains thru parks, many charming bridges over The Root River. North end signage was elusive too. We park near Zoo, biked along shore line, cut West to pick up trail just west of Main Street bridge and enjoyed 90% of the ride back toward North/car. A leisurely and scenic ride except for the navigation guessing game at beginning and end.
Officially part of the Milwaukee County Oak Leaf Trail system, this connector joins the Oak Leaf loop at Brown Deer Park and meets the Ozaukee Interurban Trail seamlessly at County Line Road. Combined with the Oak Leaf’s Lakefront, River Line and Zip Line segments, they provide straight, smooth pavement on railbed between downtown Milwaukee and Cedarburg, and beyond.
I rode this trail once to complete the last section of the 52 miles of the Heart of Vilas County Bike Trail System. The 2 1/2 mile section that is right next to the Manitowish Waters trail is excellent. From the Town Hall on Hwy 51,go west and cross the Manitowish river, then cross Co. Hwy 51. Follow the trail until you come out at Angler's bar. This section is filled with woods and a bridge and is so fun to ride through. It shouldn't be missed, it is beautiful. I would pass on the rest of the trail as you head west. It gets worse and worse as you ride. They have you going on a lot of access roads that are really boring. Once you get to Mercer there is another really boring road to ride on going into town. My advice would be to ride the first part of this trail until it connects back up to the Manitowish Waters trail at Angler's bar. Then continue on the Manitowish Waters trail and even the Crystal Lake trail, they are both outstanding and way better than the western part of the Mercer trail.
Crushed stone was upgraded to asphalt by the end of 2022. Much smoother ride from end to end. Still absent a direct link into Lakeside Park.
Rode from Mt. Horeb to Ridgeway and back. Beautiful countryside and the trail is great. All well kept. Can’t wait to go back!
I’ve ridden this trail several times. It’s well kept and beautiful!
I’ve ridden this trail several times. It’s well kept. Most of it is shady and fairly flat.
I rode just part this trail today on my electric fat tired bike (Monroe to South Wayne and back). Most of the trail is gravel/crushed limestone. I’m afraid if I didn’t have the fat tires it could have very difficult. It was a little rough also. Overall it was a beautiful ride, I just had to be very careful. It was a weekday and I didn’t see anyone else.
On a perfect weekday morning in early October I experienced by bicycle the South Shore portion of the Oak Leaf Trail.
I parked in the Grant Park Beach parking lot in South Milwaukee and headed north to Cupertino Park and then back, a distance of about twelve miles. Even though it was such a short ride it took me over two hours since I had to frequently stop for the awesome photo ops. The views of the lake and the Milwaukee skyline are sensational!
The trail is obviously beloved by the community. Not only were there plenty of other bicyclists, but there were a tremendous amount of friendly pedestrians walking their dogs or getting their steps in, especially in Bay View Park.
The South Shore portion of the trail has so much to offer: woods, tree lined streets with charming homes, wildflowers, squirrels, geese, shoreline, lots of curves, five parks, yachts, and plenty of benches to take in the marvelous views of Lake Michigan and the downtown skyline. Besides the lake views, I especially enjoyed the curvy trail covered in golden leaves through the woods of Grant Park.
TWO WORDS OF WARNING:
1) There are hills.
2) There are cracked and uplifted portions of trail through the woods of Grant Park due to tree roots. They will effectively work like speed bumps and slow you down a bit.
However, all in all, this is an enjoyable ride and certainly worthy of your time and five stars!
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