Oak Leaf Trail

The Oak Leaf Trail is a massive bike trail that loops throughout Milwaukee County on both the North and South sides of town, and throughout the major park systems.

The trail changes depending on where you’re riding it – sometimes connecting itself via city streets to ensure continuity of the trail.

My favorite part of this bike path on the North side is from just South of Hampton Avenue in Whitefish Bay all the way down to the lakefront.

The best part about this stretch of the trail is that there are NO STREETS TO CROSS OVER! You go either under or over the busy streets in the city, and even though you’re literally right next to crowded, busy areas, it feels like you’re in an entirely different world!

This portion of the path rides along the Milwaukee River, and goes past the Urban Ecology Center. It’s very peaceful, and is a nice path on slightly hot or windy days as it is protected from the sun and the wind with all of the nice shade trees.

I haven’t yet biked the South side trails, although I have friends that ride them often, and love them as much as I love the North side.

One of the longer trails on the South-East side of town goes from South Shore park all the way to Rawson Avenue. The other one starts at Coolwaters Park, and goes down through Whitnall Park and beyond.

I’m pretty darn proud of our little Milwaukee County bike paths!

For more information, check out the official website (opens new window). Maps can be found at the Milwaukee by bike website (opens new window).

Enjoy your trip!

Return from Oak Leaf Trail to Things to do in Milwaukee