The Ultimate Cycling Guide to Milwaukee, WI

Bublr Bikes Milwaukee | Courtesy of Bublr Bikes
Bublr Bikes Milwaukee | Courtesy of Bublr Bikes
Photo of Victoria Borisch
Freelance Writer21 February 2018

With investment in affordable rentals and paths along the beautiful lakeshore, cycling in Milwaukee has taken off. Whether taking part in a 24-hour race or biking to your favorite beer garden, the biggest city in Wisconsin has something for everyone who enjoys getting around on two wheels. Harley-Davidson fans aren’t the only bike enthusiasts in town anymore.

Bublr Bikes

For those who don’t have a bike of their own but want an easy and affordable way to get around Milwaukee, Bublr Bikes is the answer. This bike-share program allows people to take a bike from one Bublr station, ride it anywhere in the city, and then return it to whichever station is nearby. There are stations across the greater Milwaukee area, including in Shorewood, Wauwatosa, and West Allis. The aim of Bublr Bikes is to be a sustainable, healthy mode of transportation that is available to everyone at a low cost. From an hourly pass to an annual membership, there is a rental option suitable for every bike journey.

Bublr Bikes Milwaukee | Courtesy of Bublr Bikes

Oak Leaf Trail

The Oak Leaf Trail weaves its way through Milwaukee County for over 100 miles (161 kilometers). A cyclist’s dream, the trail can be broken down into smaller segments with loops running through all of the county’s major parkways. Thanks to its incredible length, this trail offers a wide variety of scenery from rustic woodlands to Milwaukee’s bustling downtown urban center.

Hank Aaron State Trail

The Hank Aaron State Trail is one of the two most popular cycling spots in Milwaukee. The 12 miles (19.3 kilometers) of continuous connection leads riders from Milwaukee’s lakefront through its west end. For those who want to keep on going, this trail links up with the Oak Leaf Trail on both the east and west ends.

Valley Passage on the Hank Aaron Trail | Friends of Hank Aaron State Trail

Estabrook Beer Garden

While checking out the Whitefish Bay part of the Oak Leaf Trail, be sure to stop at the Estabrook Beer Garden, the USA’s first beer garden after Prohibition. Beer and biking might not seem like two things that go together, but in fact, the word Radler (what is more commonly known as Shandy in Wisconsin) comes from the German word for cyclist.

Estabrook Beer Garden, 4600 Estabrook Parkway, Milwaukee, WI, USA, +1 414 226 2728

Cafe Hollander Downer Avenue | Courtesy of Lowlands Group

Café Hollander Downer Avenue | Courtesy of Lowlands Group

Café Hollander

Cafe, Belgian, $$$
Map View
Milwaukee’s Café Hollander is a Benelux-themed restaurant that fully embraces the Dutch cycling culture and treats cyclists stopping in as first-class citizens. Spandex is always welcome, and secure bike parking is available for visitors. From vintage bikes throughout the restaurant to racing team sponsorship, this café lets its love of cycling shine through and is a proud advocate for cycling-related causes. Weekly rides are organized through the café, and anyone looking for a fun group of people to train with is welcome to join.

Riverwest 24 bike race

The Riverwest 24 is a 24-hour bike race that takes place in Milwaukee’s Riverwest neighborhood. With the aim of encouraging urban biking and strengthening the neighborhood community, this race brings together both cyclists and spectators for a day of cycling fun. Those who aren’t feeling up to a 24-hour ride can split up the time with teammates, making it easy for anyone to take part.