Oak Leaf Trail (Milwaukee County)

Cruise Milwaukee County on the Oak Leaf Trail, a countywide greenway that links parks, neighborhoods, and the Lake Michigan lakefront. It’s mostly smooth and paved, with a few short gravel bits, weaving together park paths, riverside greenways, and calm residential streets.

Expect dedicated trail sections with lake views, shady park corridors, and easy access to beaches, picnic spots, and cafés. Wayfinding is solid—look for the oak leaf signs—but some junctions come up fast, so a map or GPS helps if you’re stitching together longer rides. Grades are gentle and the vibe is friendly, making it a great pick for families, commuters, and casual spins alike.

Ride a short segment for a quick breath of fresh air or link multiple sections for an all‑day tour. Standard road or hybrid tires are perfect; slightly wider rubber makes the occasional gravel stretch no big deal. Plenty of trailheads and park facilities along the way keep refills and breaks easy. Simple, scenic, and very Milwaukee.