Explore the best rated trails in Waupun, WI. Whether you're looking for an easy walking trail or a bike trail like the Levee Trail (Portage) and Fox River State Trail. With more than 44 trails covering 610 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
We rode the southern portion of this trail in early June 2023. We had hoped to find parking at the southern trailhead. There was only a narrow county road in which to park. We drove North about 2.5 miles and parked by local businesses that paralleled the trail. It also allowed for indoor facilities pre and post ride. Portions of the trail on the very southernmost end are rutted from large equipment, that was likely driven on the gravel when it was wet. It wasn't unrideable, just slow going. We did 15 miles up and back. There was one outhouse about 8 miles north. The trail is well maintained gravel then turns into paved asphalt with another outhouse about 15 miles north.
I absolutely love this stretch of the trail. Beautiful scenery and solid.
Super easy to walk. There is a Wheelchair accessible porta potty halfway through the trail. You’ll see lots of geese, ducks & swans. Perfect wide sidewalk for biking & couples or families walking. Plenty of benches all the way down.
Did the whole Southern segment. Was a decent trail..the usual trail trail..nothing spectacular. The part of the trail running along the water is pretty. Low rating is for the all the horse **** up n down the entire trail. The leaves this time of year really hide the piles.
A very well maintained Trail with services and many parking lots. We experienced a lot of foot and bike traffic especially as we got close to the campgrounds.
I started out my ride from my home about 9 miles north of downtown Milwaukee where I caught "the Hank" and made my way west to the Glacial Drumlin Trail. I started out at 3:00 am, so it didn't really get light out until I got to about Wales. After that, I was on non-paved trail (my personal fav) for the rest of the ride to Madison. The trail is really very nice and mostly flat with a lot of varying landscapes. Since it's October, there were a ton of migrating birds and pretty good fall colors all along the trail, and I didn't see another human riding until I was about 5 hours into my trip near Lake Mills. The only thing keeping me from giving this trail 5 stars are the bridges, which are mostly bad. They do have a rubber strip running down the middle of them which helps, but they are still mostly bouncy and you have to deal with a 3-6" rise at the start of each of them. The west end of the trail was closed near Cottage Grove, and I had to take a detour on streets, which was fine. This is a highly recommended ride, especially during fall.
Out of all the trails I’ve done, I like this one the least. Half of it’s in town and on side streets with poor signage. Once you hit the gravel part, it’s super shotty for the first 2 miles since they redid culverts n put new gravel in..I’m talking huge sharp stones that are loose. Once u get past that the rest of the decently packed gravel trail runs along the highway. I was also lunged at by some Boxer who was potentially trying to bite my ankle. It was on a leash but the owner could not control it..she just looked at me n walked away.
I started in Greenbush and went to Sheboygan. It came out to 17.2 miles, one way. Overall the surface is smooth with only a few places that were just a little rough. Lots of hills, which are normally great, because no matter how much it hurts going up, you can always coast down. Except that at the bottom of most of the hills, you have to stop at a road crossing. The views of the Kettle Moraine Forest from the hilltops were nice as the Fall colors are starting to come in. Yes, being right next to Hwy 23 was noisy and smelly from the exhaust. Overall though, I enjoyed the ride. Plenty of spots to stop and rest. A river. Wide open farmland. I guess this trail could suck or be fantastic, depending on one's expectations and perspective.
The Milwaukee County Parks, Oak Leaf Trail webpage says the extension of the South Shore Line segment is open to Bender Park. It is not yet show on the TrailLink map. On my September 2022 trip up to the Oak Leaf Trail, to do the original South Shore Line and the Oak Creek Line, I decided to see what the new extension was like. Yes, it is open with routing signs in place and a creek bridge constructed. But the surface is made up of 1-inch sized crushed stone which is typically used as a base layer under asphalt pavement. Even though I have a gravel bike, from Drexel Ave I only made it down to Pennsylvania Ave and gave up the going further. It’s just too rough. I made the trip back using highways. I searched on the internet, and it seems that the funding grants describe a 2023 completion. I hope what is the case is the asphalt paving will be done in 2023.
On my third trip up to the Oak Leaf Trail I did what I call the Southeast Quadrant. I parked at Greenlawn Park and did the trail and spurs down to the Racine County line and up to Cupertino Park near the Lake Michigan Ferry. What I liked about this trip was the variety in the trail. Segments consisted of rails to trails (with powerlines), trail in parks, separate trails on arterial streets, the parkway roads, and rural highways. The long, southerly segment in the forest on the bluffs along Lake Michigan was the prettiest segment of my three trips on the Oak Leaf Trail. The north segment along Lake Michigan was closer to the water and gave a nice view of downtown Milwaukee.
One concern is the trail is being extended to Bender Park, which is popular but what about funding of maintenance of the trail that already exists? This section had some of the asphalt showing its age with the periodic shrinkage cracks giving that frequent bothersome bump. One hidden path bridge at the bottom of a hill had plywood covering over rotted deck boards, which at speed was very rough. But none of these maintenance issues should stop any one from coming to use the Oak Leaf Trail. I do recommend stopping at the coffee/ice cream store the trail parkway passes at Chicago Ave.
I am sure the rail to trail segment from Greenlawn Park was the former North Shore Interurban Line (to Chicago) that my folks took on their honeymoon to Milwaukee in 1944.
Great trail; all paved. Lots of things to do along the way; many different stopping places available!
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