Explore the Oak Leaf Discovery Tour: 135 Miles of Family Fun
Few places capture Milwaukee’s mix of lakeshore beauty, urban history, and neighborhood parks like the Oak Leaf Trail. Stretching 135 miles and arranged as nine color-coded “lines,” the trail lets walkers, runners, and cyclists weave through woodlands, river corridors, and lakefront vistas in every corner of the county, including beautiful stretches throughout the North Shore.
What Is the Oak Leaf Discovery Tour (OLDT)?
To turn an ordinary outing into a true adventure, The Park People created the Oak Leaf Discovery Tour, a mobile “passport” that highlights 50-plus points of interest—think public art, historic bridges, hidden beaches, and even a few selfie spots. Each time you tap a stop inside the $5 app, the passport stamps your progress and unlocks special offers from local businesses along the way.
Ride (or Stroll) in Style
For 2025, the OLDT package adds a soft Bella + Canvas cotton tee in a neutral hue—perfect for layering on cool lake breezes. The combo ($35, shipping included) bundles the digital passport and the exclusive shirt; the tee isn’t sold separately, so this is the only way to snag one.
How to Get Started
Purchase the digital passport (only $5!) or tee/app combo through The Park People.
Within a day or two you’ll receive an email link. Enter your email, receive a one-time access code, and you’re in—no passwords to remember.
Open the passport whenever you hit the trail; a fresh code arrives in seconds.
North Shore Highlights to Check Off First
• Estabrook Park & Beer Garden (Lake Line): Spot herons along the river, then reward yourself with a root beer (or the grown-up kind).
• Hubbard Park Swing Bridge (Lake Line): A quick detour off the trail leads to this photogenic iron span over the Milwaukee River.
• Brown Deer Park Lagoon (Milwaukee River Line): Pack a picnic and watch anglers cast for bluegill.
• Doctors Park Bluff Overlook (Lake Loop Connector): One of the best sunrise views on the entire system.
• Glendale’s Kletzsch Park Falls (Milwaukee River Line): An easy family bike from Fox Point with plenty of shaded play space.
Make It a Season-Long Challenge
Check off ten or more points and you’ll qualify for prize drawings at the end-of-season OLDT party on September 15 at South Shore Terrace. It’s a laid-back way to celebrate your miles alongside fellow trail fans.
Ready to Roll?
The Oak Leaf Discovery Tour adds purpose—and a little swag—to every outing. Grab your digital passport (and that ultra-comfy tee), share your favorite stops with the North Shore Family Adventures community, and let the trail surprise you at every turn.
Want to find more trails to bike and explore? See our Milwaukee North Shore by bike guide.
See you out there on the Oak Leaf!
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