Explore the best rated trails in Milwaukee, WI, whether you're looking for an easy walking trail or a bike trail like the Wild Goose State Trail and New Berlin Recreation Trail . With more than 56 trails covering 748 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 came to Milwaukee specifically to ride this trail. Over the course of three days I put a little over 100 miles on my bike, which did include some backtracking. I'd say we rode maybe 60% of the trail. The majority of what we rode was gorgeous and incredibly well maintained. In particular, the lakeshore section from South Shore park to Grant Park was incredible. The Whitnall Park/Root River route on the western edge of the Oak Leaf loop was also a wonderful ride. We rode from riverside park out to Glendale; if you do this portion make sure to ride up into the Arboretum, it was amazing. (And you will find restrooms there). On a less positive note , the East/west route that bisects the Oak Leaf Loop was barely a trail, more o
It’s a beautiful trail … well maintained! Quite a bit of shade for the most part we started In Fond du Lac off rolling meadows rd. Biked to the Horicon Marsh loop. I would recommend stopped at Katy’s Log Cabin in Oakfield for a good bloody and/or a great lunch !
I did this trail on bike 2 years ago and I hated it, signage is terrible, at one point after Golf road, you literally come to an end and have to carry your bike over train tracks and active train tracks. No signs of any sort. You go through a campground that confuses you even more. I won’t do it again. To ridiculous.
Since the tornado in May 2025 there is two miles of trees down not far from Juneau. It is impassable. I rerouted from prospect onto Hwy 26 to Swan Rd.
I enjoyed the south half but the part through the city was not well or marked at all. Route would be vastly improved with some signage.
Started at the depot in Oostburg and headed north. After a few blocks we re-checked the app and saw it was just a bike *route*, not really a trail. We turned around and went back. No idea why this is considered a trail. It’s just a bike route. I don’t mind sharing with cars for short sections but I don’t consider riding busy country roads for miles worthy of “trail” designation.
Started in McHenry and went south. Did 33 miles round trip. McHenry to Crystal Lake lots of ruts and bumpy. Just north of Crystal Lake becomes a new, very smooth trail, but is extremely hilly with lots of turns. After going through a small section of downtown Crystal Lake becomes not as hilly to Algonquin.
Can confirm that many lazy and inconsiderate dog owners leave their dog's poops right on the trail, so keep an eye out for landmnes. Also beware that many people do not have their dogs on leashes, so have protection on you and stay vigilant. Beautiful farmland scenery starting from the Vandenboom trailhead heading west. Very flat, and occasional holes in trail possibly from critters. Nice that each road you reach from the trailhead is just about 1 mile so it's easy to gauge the distance you've walked.
Late April Sunday in clear weather. Started at southern end as marked on Traillink map. There is no dedicated parking but on-street parking in surrounding residential neighborhood was without issues. Rode north to McHenry, 16 miles. Surface is newly or recently repaved and excellent, until you reach Pleasant Hill Road, then only fair, with expansion cracks every 50 60 feet, bumpy ride into McHenry but very doable. Generally pleasant, only partially shaded ride, but not the most picturesque.
2 issues around Crystal Lake, first, signage for on-road traverse of the town is inadequate in both directions. Going north, 2 blocks after crossing the railroad tracks, you have to jog East from Main Street 3 blocks to Glen Ave., then cross IL 176 onto Lorraine Dr. to reach the continuation of the trail into Sterne's Woods. Visa versa coming south. Second, be aware there are several short but steep climbs and descents going through Sterne's Woods. Seamless continuation onto Fox River trail at southern end.
It’s pretty scenic, especially with the leaf colors. Also pretty busy! There’s parking on both ends. A lot of the trail is grass, not even gravel. The spot where it’s asphalt is very minimal. It’s awesome you can stop and ride through Horicon Marsh! Lots of kitties on this trail ¿
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