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Explore the best rated trails in Milwaukee, WI. Whether you're looking for an easy walking trail or a bike trail like the Seven Waters Bike Trail (Route of the Badger) and New Berlin Recreation Trail. With more than 55 trails covering 736 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.
I've ridden this trail for 30 years and it's well maintained and relatively flat. The crushed limestone surface drains water away quickly though in winter, when the ground is frozen, the water can form puddles or freeze so you must be careful. After bigger rainstorms, some of the underpasses can be impassable (e.g., Route 60 especially--there is a side path that connects the trail but you need to cross a major road). The path gets multi-modal usage, from walkers, families, runners, horses, skiers, bicycles, to e-bikes. You can ride this with a road bike if you're confident but cross or gravel bikes are better but certainly not absolutely necessary. Nowadays we see fat-tire bikes, especially in winter, and e-bikes too. People are generally quite respectful of others. The trail is well marked and I recommend starting at Daniel Wright Woods or Old School Forest Preserve which are in southern Lake County. As others have said, going north from there keeps you in Lake County which does a great job of maintaining the trails.
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.
I had ridden the northern end of the Prairie trail & saw the sign forg the Hebron trail so decided one day to check it out. Rode from the Prairie Trail junction to the “trail end” at Lange Road & back again. About an hour round trip but that included stopping to take photos. It’s a well groomed trail, plenty wide for comfortable passing of others. West of Keystone Road crossing is pretty much straight & flat but scenery still varies.
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.
I started from the south entry point and only made it a few miles in before deciding to just take the roads back south. It hadn't rained for a few days and the bridge underpasses were still full of pooled water and soft mud. I don't even know if I'd ride through them on a mountain bike unless I was really looking to get nasty.
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!
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.
Extends beyond the old wade house now. Started there and ended in Sheboygan. First long ride on the new eBikes. 360 mapped it and loaded to street view.
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