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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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.
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!
Super nice paved trail with lovely views! Only bummer is the trail is closed going into some park? at the end. Runs through a reservation land which is interesting. Has a cool sundial along the trail.
This trail is super nice I think. Has some pretty views the whole way too. Liked it so much I did it twice in October! Came back a 2nd time to see the colors in the rolling hills. I think Fall is the best time to bike this one.
This trail was actually a former C&NW railway that served Lake Geneva and terminated in Williams Bay. Service to Williams Bay started in 1888 and ended in 1965. Service to Lake Geneva ended in 1975. Thanks to Maxine Thoorsell for starting the conversion of turning this former railway into a nature trail. It is an easy grass covered walk and the trail is 1.7 miles in length. You can also access the trail at the boat launch to the west...behind the barn. A separate trail that is part of this former railway extends from Williams Bay Northeast up to Hwy 50 in the Kishwaukeetoe Conservancy
Rode the trail today from Beloit to Janesville and back. Of course, the trees were gorgeous! The path is paved the whole way. Much of the trail is along the river.
My husband and rode from Lone Rock to Richland Center and back. The colors on the trees were beautiful! The trail was in good shape. It ranges from crushed limestone to paved. There is a small section that is a tiny bit rough, but we have fat tire bikes so it was no problem. It’s all pretty flat. We saw marshes, creeks, farmland, and wooded areas. There are several wooden bridges, all in great shape.
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