Exploring the Oak Leaf

This October, our blog is focusing on one of Milwaukee’s true gems — the Oak Leaf Trail! As the leaves change and a crisp autumn breeze sweeps in from Lake Michigan, there’s no better time to lace up, hop on a bike, or get out for a stroll to explore this gorgeous trail. Whether you’re looking for a scenic workout or want to soak in the beauty of fall while staying at The Plaza, we’ve prepared a guide to making the most of the Oak Leaf Trail.

Now for some history: the Oak Leaf Trail planning dates back to the 1930s, but construction didn’t officially begin until the 1960s. Originally dubbed the 76 Bike Trail to celebrate the nation’s bicentennial, it got its current name in 1996, as a nod to the region’s oak-tree-lined parkways and natural beauty.

Stretching over 135 miles, the Oak Leaf Trail offers perfectly paved paths for cycling, rollerblading, walking, birdwatching, and running all across Milwaukee County. You can explore its beauty year-round, but fall is a special time to see its colors change and put on a colorful show as it winds its way through the foliage. Nearly a quarter of the trail runs along the stunning shores of Lake Michigan, with stops at beer gardens, parks, and public spaces along the path.

For those staying with us at The Plaza, it’s practically in our backyard! One trailhead starts just three blocks east in Juneau Park. You can take the Lake Line south toward the North Point Lighthouse or head north on the Milwaukee River Line up to Estabrook Beer Garden. The Zip Line will even take you as far as to Brown Deer!

For an easy way to explore, grab a Bublr Bike — Milwaukee’s bike sharing program. The closest stations are just a short walk away: Cathedral Square is about eight minutes from The Plaza, or head north from Juneau Park to the Burns Commons station.

What’s better than a biking adventure ending with a treat? Take a ride and stop for some ice cream, or hit up one of Milwaukee’s famous beer gardens along the trail for a crisp pint of Oktoberfest. After all that exploring, we’ll be ready to welcome you back to our cozy Plaza Hotel for some well-deserved relaxation.

Happy trails, and enjoy Milwaukee’s fall colors while they last!