Pedaling Through Parks: A Perfect October Ride on the Oak Leaf Trail. David Schneider

AUTHOR: David Schneider

There are few better ways to spend a warm October day than in the parks and Milwaukee’s Oak Leaf Trail delivers the perfect route for park lovers.

A few friends and I kicked off our Sunday morning on October 5th at Greenfield Park in West Allis. We gathered for the 2025 Walk to Defeat ALS Milwaukee, which is a great cause with a strong turnout of over 3,000 supporters. With the borrowed summer weather, we packed up our bikes and headed to the east side of Milwaukee for a ride through the parks and probably our last dip in Lake Michigan for the season, probably.

We started our ride at Grant Park, where the mix of lakefront views and bursts of autumn color through the woodsy trails set the stage. Our destination for the day was the South Shore Terrace beer garden, with a few stops in between along Oak Leaf Trail South Shore Line, including Warnimont Park, Sheridan Park and Bay View Park.

The leaves may be turning, but the sunshine felt more like summer—a reminder of how lucky we are to enjoy this stretch of the season in Milwaukee. As we pedaled north, the trail carried us through a scenic mix of wooded paths and lakefront stretches. The crisp air, crunch of leaves, and pops of red, gold, and orange created a postcard backdrop. What I love most about the Oak Leaf Trail is how it strings together so many of Milwaukee’s green spaces, giving you a front-row seat to the parks that make this city shine.

There’s nothing better than rolling up to South Shore Park and grabbing a table with a view of Lake Michigan. A round of local brews and a pretzel made for the perfect reward after a few miles of riding. Beer gardens are one of Milwaukee County Parks’ best traditions—bringing people together to connect and celebrate the outdoors. After our brief stop, we routed back to where we started at Grant Park beach, and concluded the adventure with a plunge into Lake Michigan.

Moments like these are why the Milwaukee Parks Foundation matters. The resources ensure that our trails stay connected, our parks stay vibrant, and our community continues to have access to these incredible spaces. Whether you’re biking, walking, swimming, or just soaking in the view with friends, supporting our parks means investing in experiences like this one. And if a sunny October ride ends with good friends, good beer, and a lakefront view, I can’t think of a better reason to keep riding—and keep giving back to the parks that make it all possible.