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Explore the best rated trails in Watertown, WI. Whether you're looking for an easy walking trail or a bike trail like the Levee Trail (Portage) and Peebles Trail. With more than 62 trails covering 708 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.
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.
Took advantage of the mild weather forecasted and did the ride I had put off all summer. The fall leaves were just beyond their peak but still quite colorful. The trail surface was good except for some sections between Ridgeway and Dodgeville that were rutty and sandy. Restrooms were still open in Mt Horeb, Barneveld, and Ridgeway.
Stopped at the Brix cidery in Mt Horeb for cider and an apple cider doughnut. Stayed overnight at the Pine Ridge motel in Dodgeville - clean, quiet and only a couple hundred yards from the trail.
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.
It's a pretty trail and nice and quiet, but not trike friendly. With two lanes separated by a grassy strip, I was always dragging one or two wheels through the grass so it was a bit of a rough ride and slow. The lanes are pretty smooth, so two-wheelers will not have a problem, but it's not a great ride for a recumbent trike
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.
The trail is longer now as it ends at Beloit's Big Hills Park. Scenic ride on new asphalt one section on the road to cross Bass Creek in Afton. Several other short sections on roads but well marked. Go up to the park's observation platform for a vista of the Rock River.
Great trail; all paved. Lots of things to do along the way; many different stopping places available!
Love this trail! Can find several restaurants to eat at, play miniature golf, get a great cup of coffee all on the trail! Great trail!
Love this trail! Beautiful ride; worth the trip to ride.
Starting at the Brown Deer Village Park and heading south, I did what I call the NE Quadrant of the Oak Leaf Trail, consisting of the trail north of downtown Milwaukee. If you look at the trail map, there are some loop segments and some spurs that can be done. I did them all. Some segments are on old railroad beds and some on subdivision roads or separated bike lanes. Some sections were newly paved. You head back north after reaching downtown Milwaukee, but I stopped for lunch at the brat/beer garden along the trail at the art museum. Especially useful is having the downloaded TrailLink map as the connection to the parts of the Oak Leaf Trail south of downtown are not that well marked at the ongoing highway construction. There were good trail signs at other periodic locations.
I give this trail 5 stars. It is now a paved ride from Big Hill Park (Beloit) to Janesville Wi.
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