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Explore the best rated trails in Caledonia, WI. Whether you're looking for an easy walking trail or a bike trail like the New Berlin Recreation Trail and Brown Deer Recreational Trail. With more than 69 trails covering 830 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.
This trail begins off of Voltz near Sunset Ridge and goes about a mile and a half or so across Sunset up to Dundee Rd. If riding through Northbrook, it's a very handy way to avoid Skokie Blvd and make your way up to the North Trail entrance off of Dundee across from Botanic Gardens. It's mostly just a nice, secluded, wooded, but paved strand behind some residential neighborhoods and runs parallel to Skokie. When riding, please be a little more mindful of residents walking, often with dogs and children. It doesn't get very crowded, and people generally aren't expecting bikers like on the major trails.
A great place for walkers, hikers, bikers, and families. It’s been wonderfully restored and brings nice surprises during each season.
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 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!
I started from a local community center near the south end, (asking permission to park my car there first). Also gave them a small donation when I returned. Most of this trail hugs the coastline, though the last few miles is along city streets. At the northwestern end of the trail, I found it joined up with a local rail trail, which runs from 3 Mile Road to Layard Ave. paralleling Douglas Ave., though it is not on Traillink. So I took that a few miles south and rode some city streets until I rejoined the Lake Michigan Pathway. In several places, the trail is not obvious or well marked, so keep your traillink app open to see where you are if you aren't sure. I recall one spot that looked like an alley past an industrial area, but it went down to the marina and the trail. Once past that, there are signs periodically to point you the right way.
The trail is closed at mile 6. There is little, if any signage for the detour. Take Old Elm Rd east to pick up the North shore trail to bypass the closure.
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.
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