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Get on your bike: Milwaukee’s best places to push your pedals

Milwaukee's many trail options for cyclists wind through places like (from left) Grant Park, Lakeshore Park and the Ozaukee Interurban Trail.
Milwaukee's many trail options for cyclists wind through places like (from left) Grant Park, Lakeshore Park and the Ozaukee Interurban Trail.

Being the active, environmentally conscious staff that we are, Radio Milwaukee has a lot of cycling knowledge within its four walls. So as soon as the conditions start to cooperate, we start sharing tips and tricks, routes and rides. But why keep it all to ourselves?

As we move through the month of May, we’ll bring you a few things we’ve learned while rolling around the city — starting today with some of the best places to bike in Milwaukee. Take a look at our suggestions below and, if you find them helpful, add them to the list of reasons for supporting us by becoming a member. Added bonus: Everyone who donates during May will be entered for a chance to win this handsome bicycle courtesy of our friends at Fyxation.

Oak Leaf Trail: Downtown to Shorewood

As a lifelong and sometimes avid biker — to the point that it’s actually a part of my reputation — I sometimes get asked where I like to bike. Fair question. I’ve biked everywhere in this city, in large part because it was literally my only form of transport for many years.

I could talk for days about the bikes I’ve owned, get granular about bike specs and regale you with stories of flat tires, accidents I’ve been in or even bike-to-car courtesy. But today, I just want to tell you about my favorite place to ride.

That’s a tough one because I definitely enjoy biking everywhere. Often the most random ride is my favorite, but let’s get specific. These days, it’s mostly about “who” rather than “where” because I love going on rides with my son and my wife. This usually happens all together and often on my favorite intercity route, The Oak Leaf Trail.

My favorite part of this massive throughway that runs 135 miles and connects all the major parks in Milwaukee is the downtown-to-Shorewood section. From there, it’s an easy jump off to home in Riverwest. I love the bike commute from Radio Milwaukee, but when I ride for fun with my family, it’s usually to a beer garden.

Now that my son can really ride, we love to hit Estabrook or Hubbard Park. There are great spots to stop and enjoy the lazy flow of the Milwaukee River, and I’ve found the trail a great spot to teach my son road etiquette, avoid the cars and sort of sail through the urban environment surrounded by nature. It’s our escape while still being in the middle of it all.

— Marcus Doucette

Hank Aaron State Trail: Lakeshore Park

Taking the Hank Aaron State Trail through Lakeshore Park from the Milwaukee Art Museum is one of my favorite bike journeys of late. Once at Lakeshore, I’m sandwiched between the lakefront and the inlet next to Henry Maier Festival Park, exposing a new side of the Summerfest grounds.

At this park in particular, it feels like life stands still as I move through it. Catch this path at the right time, and you get to see the sun setting against the water while you pass the Milwaukee skyline that bleeds from Downtown to Walker's Point.

Milwaukee Recreation

If you’ve got the fuel in you, follow this through to East Erie Street, take a ride underneath the Hoan bridge and — at great convenience — wind up right outside the hallowed halls of Radio Milwaukee on East Pittsburgh Avenue. It’s a great route to avoid Downtown traffic and The Hop tracks while offering a new perspective of the city and a reminder that you’re meant to be in the city of Milwaukee.

Bonus pick: Take the Swing Park bridge to cross from the Lower East Side to Riverwest. For a brief moment, there’s a view from the bridge that looks all the way down the Milwaukee River and is even better at night.

At the other end of the bridge lies Kadish Park with a skyline view like no other. You just gotta be able to deal with the short but healthy incline. Wait until nightfall to bike back for a view of the lit-up skyline while heading down Booth Street to East Glover Avenue, then back down the Kadish Park hill on the Oak Leaf Trail. You get the feeling of a magic carpet ride but with the lights on Lakefront Brewery’s exterior instead of stars. Still cute.

There’s a sense of pride that comes from being in control of your own transportation, the high that comes from a workout and the difference it makes for the planet. Beyond that, biking and group rides in Milwaukee are one of the greatest ways to meet new people and feel connected to the community while getting to know the landscape of your home. For me, biking remains the ultimate freedom.

— Carolann Grzybowski

Oak Leaf Trail: Cupertino to Grant Park

While there are plenty of ways to experience the 135-mile-long Oak Leaf Trail, my favorite (relatively easy) bike ride starts at Cupertino Park in Bay View and heads south on the Oak Leaf to Grant Park and back. It’s a scenic ride along the lake and takes you through six beautiful Milwaukee County Parks: Cupertino, South Shore, Bay View, Sheridan, Warnimont and Grant.

A section of The Oak Leaf
A section of the Oak Leaf Trail that runs through Grant Park in Milwaukee.

Every year on my birthday, I go for a bike ride that’s equal in miles to my age. For the last few years, I’ve been taking the Oak Leaf north to the Interurban Trail in Ozaukee County. It’s a nonstop paved trail from Downtown Milwaukee to Port Washington that, to quote Ferris Bueller, is so choice.

I’ve also been an avid user of the Hank Aaron State Trail since it opened in 2006. The 14-mile path starts at the Mitchell Park Domes and heads straight west to the Milwaukee-Waukesha County line. It easily connects to the New Berlin Trail, which then hooks up with the Glacial Drumlin Trail for those looking for a more extended bike ride.

Pro tip: avoid parking and lines of cars by taking the Hank Aaron State Trail to American Family Field, Wisconsin State Fair or the Milwaukee County Zoo. While you’re at it, you can also stop by the Menomonee Valley branch of the Urban Ecology Center.

The most Milwaukee experience I recommend is incorporating Milwaukee’s wonderful biking trails with our beer gardens and local breweries. Juneau, South Shore, Hubbard, Estabrook, Hoyt and Whitnall Park beer gardens are all off the Oak Leaf Trail. And the Vine Humboldt and McKinley Marina beer gardens aren’t too far from OLT either. City Lights and Third Space Brewing companies are a short ride from the Hank Aaron State Trail.

With all of those options, a tour of Milwaukee beer gardens and breweries would be easy to put together. Just be safe and look out for train tracks.

— Jay Burseth

Ozaukee Interurban Trail

Since my colleagues have Milwaukee well covered, I’m going to hold it down for the North Shore and the fantastic Ozaukee Interurban Trail that runs the full length of the county. Let’s start with the big three along the 30-mile stretch: Mequon, Cedarburg and Port Washington — all of which can serve as a jumping-off point or a destination.

Mequon has its own public market mere steps from the trail with enough options (Good City Brewing and Purple Door among them) to satisfy most appetites. If you depart the trail in the other direction, you’ve got the baaree beer garden, the always bike-friendly Cafe Hollander, and coffee options from Colectivo and Fiddleheads.

Cedarburg is the history-leaning member of the trifecta — so much so that literally its entire main drag is on the National Register of Historic Places. You can amble up and down Washington Avenue taking in the architecture if you’re the Bobby Tanzilo type, but the must-stop spots are Amy’s Candy Kitchen for a $10+ caramel apple (trust me, it’s worth every cent), the Union House for small plates/cocktails and the Cedar Creek Settlement for coffee, crepes, shopping, wine and more.

Then you’ve got Port Washington and the unfair advantage of Lake Michigan. Does that make it a potentially windy part of your ride? It does. But the views are wonderful, Dockside Deli is a convenient all-purpose and all-ages refueling station, Inventors Brewpub has the beer side of things covered, and you can hit up a lighthouse that’s more than 160 years old.

Oh yeah, there’s also the actual biking part of the trail. It’s a very well-kept pathway that improved greatly with the 2009 completion of the bridge over I-43 just south of Port Washington. Long stretches of your ride can be downright serene, and it’s fairly friendly to all ages, with the most challenging part between Grafton and Port Washington.

As a bonus, it also connects to the Oak Leaf Trail in the south, which means the more hardy riders could start in Ozaukee County and reach any of the places mentioned by my colleagues.

A quick tip from my own attempt to do this a few years back: Before you make the commitment to solo ride from Cedarburg to the Estabrook Park Beer Garden, call ahead to see if it’s open.

— Brett Krzykowski

The bridge spanning I-43 on the Ozaukee Interurban Trail near Port Washington.
Kyle Coppersmith
The bridge spanning I-43 on the Ozaukee Interurban Trail near Port Washington.