1. Oak Leaf Trail

    1. Oak Leaf Trail

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    Oak Leaf Trail

    4.7 (39 reviews)

    Oak Leaf Trail Photos

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    View of trail by the Urban Ecology Center.
    Howard L.

    I can tell this is a delightful city trail and we saw but a snippet of it.  We started our Sunday morning stroll by the Urban Ecology Center.  The trail is wide, well paved, and tranquil here. Where we were at was below grade and below a multitude of bridges and it felt like we were walking in a large, quaint outdoor subway.  There were intermittent encounters with courteous walkers, bikers, joggers, and dog walkers and it was nicely uncrowded at this time.  I definitely would like to see more of this extensive and locally renowned trail and plan to on future visits.  Thanks to Yelper Sarah P for her insightful trail review and tips. Note that there are two Yelp pages for this trail, but this is the more popular one.

    Aubrey G.

    Oak Leaf Trail is part of one of my favorite exercise walks near and about the Tosa village. The path bends and takes you along the Menomonee River Parkway and parallels (west) Honey Creek Parkway as well. I admire how the municipal parks takes care of the area. I feel like I'm miles away from the "city" when I walk the trail. At one point, a bridge crosses the Menomonee River. I can stand on that bridge and gaze at the rushing water all day. If you are a runner/jogger/walker for exercise and live in the area, I strongly encourage you to check it out for yourself!

    North towards Mequon
    Chadrick J.

    To know we have this wonderful trail, that extends throughout Milwaukee and beyond, plus it's well maintained through and through, is just simply amazing! I've taken this trail all the way down to Summerfest grounds and further in either direction. It's paved and wide and great to get around to just about anywhere in Milwaukee. Long summer jaunts are the best on the Oak Leaf. We even have a tiny sliver of it that runs through the back lot area of our Riverwest home. So much goes on around this trail such as the Riverwest 24. It's just a piece of what makes MKE such a great city. On the Beerline section through backside of Humboldt is another section we frequent. Walking the dog or going off the trail down to the river is the best. Cutting down the trail through the Eastside takes you past and under so much of the hecticness that's going on above. Pull the trail up on Google maps and see the expanse of it and how far you can go! Good stuff Wisconsin!

    Yes ladies and gentlemen, that's a parrot on a bike. Oh the things u see on the OLT :)
    Erin L.

    This is Griffin (my doggie) and my new favorite trail in the city limits of Milwaukee. Mostly because it is a gem I found so close to my house and that it is full of other people in the area that appreciate a little nature break in the middle of their busy days. Note: My review is for the Greenfield area portion of the trail.

    Shane H.

    You cannot dismiss the importance of having the Oak Leaf Trail in a city the size of Milwaukee. It is an amazing thing that city planners even had the foresight to take on a project like this. I bike the trail to get pretty much anywhere along the city's eastern half...I haven't even explored it's other expanses, which apparently covers over 100 miles! It is one of the many things that makes me really proud to call this place home.

    Starting point of the off road portion of trail in Bayview
    Lisa A.

    We're in the thick of summer here, so I felt it would be a good time to update one of the places I spend more time than any other during June, July and August. The oak leaf trail has been many things to me. It meanders all over the city, with bike lanes on roads connecting the off road trail. It includes: 1.) The beautiful urban (yet wooded) area by the lakefront - my "everyday" part of the trail that I have probably spent 1000s (literally) of hours on over the past couple decades. 2.) The path through estabrook park that makes the beer garden there so easy to get to. 3.) The sections way out by lovers lane and the menomonee river parkway that I've walked on many times during my lunch break. 4.) The sections that start at Cupertino park in Bayview and go way down the south shore into Cudahy offering really spectacular views of the lake (many from high above it) and the Milwaukee skyline in the distance. 5.) The trail that connects the Brady street area with riverwest, on a well paved trail between the river and Humboldt park, ending at Gordon park (and making the Tracks that much easier for me to get to.) 6.) There's a nice,long well-paved stretch on the northwest side, starting just past Lincoln park and Silver Spring Drive, continuing all the way up to connect to the Ozaukee Interurban Trail. It passes by meadows, woodsy areas, parks, and a few watering holes from 20-something days gone by (I see you, Thirsty Fox and Libby Montana) My grumblings: 1.) Some parts of it are super bumpy and need a good pave job. 2.) I have mentioned that I take the green line bus from Brady st to the airport when I need to take a trip out of town. When I'm on the "on road" portions of this trail along kk and 1st & am passed by the green line bus, I contemplate my life and wonder if I'll ever make it back on a plane again in one piece in this lifetime - cuz between the cars, buses, and opening car doors -- well, its a wee bit hair raising! Just kidding (sort of) - they've repaved part of KK but some parts are still a little rough. But overall a great great trail that I'm always glad to have in our city. Many cities have multi-use trails like this but I really think ours is five star worthy.

    View from st Francis (having trouble zooming in with the cold hands)
    Peter C.

    I've been on this trail down on the east side and through Shorewood yet have recently been biking to work and taking it up by Brown Deer park. The trail connects to the inner-urban trail once you hit Ozaukee County. The trail has many side paths that lead through various parks and is clearly marked on if there are turns on the trail coming up or various streets to know where you are at. The other bikers and walkers all are very nice on the trail. The path starting at County Line Rd. in Brown Deer has been redone all the way down to around Brown Deer Park. The trail is extremely smooth and wide to pass with comfort.

    Brian M.

    I feel bad about being the first person to give the trail less than five stars, but I feel it is a very fair reflection of the entire trail. I grew up in Cudahy, so the Grant Park to the South Shore Yacht Club was a daily ritual for me in summer. Now that I have lived in Tosa for the past 10 years, I have become very familiar with the trail from the Art Museum through the East Side all the way up the White Fish Bay. As much as I really miss my old "southside ride," I really enjoy the Northshore segment. It has a nice gentle uphill grade for the entire ride heading north resulting in an awesome downhill return trip. Very enjoyable! I also regularly ride through Tosa and the Hank Aaron Trail. My favorite part is going past Miller Park and the VA. Some great scenery! My only issue with the trails are the sections of surface roads that link the various paths and parkways. As much as I love the Hank Aaron trail, the section from the Harley Museum to the lakefront is by no means a safe and tranquil route. Another example is if you are heading north into downtown from Bayview, they "trail" goes along KK Ave. Always interesting dodging buses while avoiding potholes. Also, there are some areas of the bike path that are in desperate need of resurfacing. Don't see that happening anytime soon. Thanks Mr. Walker! Having said that, the trail truly is a gem in Milwaukee County's tarnishing crown. I love it! This town wouldn't be the same without it.

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    Ask the Community - Oak Leaf Trail

    Review Highlights - Oak Leaf Trail

    As other reviewers have noted, the trail itself is a real gem to Milwaukee County.

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    Lake Park

    Lake Park

    4.7
    (36 reviews)
    3.6 km

    For Mother's Day, we decided to skip the big fancy brunch, and instead grab coffees and pastries to…read morebring on a walk. It's been quite some time since we've visited Lake Park, but I absolutely love it here! We were actually kicking ourselves that we don't come here more often to enjoy nature, as it really is beautiful in all seasons. There is no shortage of trails, short or long, that wind through the park and dip down into the ravines. This includes stairs and some rockier walk ways that lead out to the lakefront. If you prefer to stay on the flat road, you can enjoy the well-paved paths by foot or by bike. We had our stroller along and were able to push it throughout. You'll pass by a golf course, the fancy Lake Park Bistro restaurant, lawn bowling greens, statues, and even the infamous Milwaukee light house. Looking forward to the summertime in hopes that the weekly concert series returns to this park, in addition to the traveling beer garden. My son should be walking soon enough, so we'll no doubt return to let him run free and get some fresh air, while we enjoy views of the lake!

    Lake Park is one of my favorite running and wall spots. It's so beautiful and peaceful with easy…read moreaccess to the beach. I like getting there early in the morning to see the sun rise over the lake. There's so much history to this location. I loved learning more from the Wisconsin Historical Society about how the park was designed and constructed. It's a really cool spot for everyone: runners, walkers, people with dogs or kids, everyone! Enjoy!

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    Lake Park
    Lake Park
    Lake Park

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    Oak Leaf Trail - parks - Updated July 2026

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