Milwaukee Riverwalk

6 Reasons I Love Milwaukee: Dan Simmons

Having lived outside of Wisconsin and the States, Dan Simmons has a unique appreciation for all Milwaukee has to offer.

We asked writer and January 2018 issue contributor Dan Simmons to share with us the reasons he loves Milwaukee. Here are his picks:


Across the street from my house in Shorewood one fall day, I encountered a group of older Polish-American fly fishermen carrying salmon as big as their forearms that they’d caught in the Milwaukee River. They were headed back to Chicago from Hubbard Park to enjoy their catch.

Six blocks the other direction one winter day, I came upon Tamir, a recent transplant from Malibu fresh out of Lake Michigan. His beard dangled icicles. An ice halo circled his wetsuit hood. He was severely stoked about the waves he surfed that day, when it was in the single digits.

These two assets –the river and the lake – bring endless opportunities for recreation. But they also attract interesting people doing interesting things. Plus, they’re nice to look at. I don’t always do hill repeats, but when I do, I prefer doing them up and down the switchbacks beside Lake Michigan at Atwater Park. I often forget I’m in Milwaukee and flash back to Carlsbad, the dreamy town in Southern California that used to be my go-to beach getaway. The view of Lake Michigan on a sunny day with the waves lapping ashore isn’t much different than the view of the Pacific. It’s a scenic place to suffer.


The Oak Leaf Trail gets the attention, and rightly so. It’s a stunner. But the dirt trails that weave through the woods between the Oak Leaf and the water also invite me in to explore. It’s remarkable to be able to off-road right in the city. Whoever created those trails and maintains them, you’re my hero. Plus, microadventures await throughout the trail system. Today I discovered an abandoned stone tunnel, with a gigantic cave-like space open on one end. Graffiti and evidence of illicit activities of many varieties abounded. What’s not to love?

Outdoor ping pong

If there’s one thing I love more than ping pong, it’s outdoor ping pong. And there are three different courts within walking distance of my house. This reminds me of living in China, where I’d regularly join pickup games at parks and get schooled by 7-year-olds and their grandmothers. I’d love it if the local courts could install lights for night games, but I can just get creative with headlights and headlamps, too.


Green Bay and Madison can have their football traditions. I’m giddy to live in a town that’s hoops-obsessed and where football doesn’t exist, where Kareem and Oscar and Sidney and Big Dog played and Al Mcguire coached. And is “Teach my daughter to pronounce Giannis Antetokounmpo” on my list of New Year’s resolutions? Of course it is. Bonus points for being Latrell Sprewell’s hometown.

Beer and children

Estabrook Park Beer GardenIn more prudish cities, kids’ activities exist in a different space than parents’ activities, and parents spend too much time with the shorties wishing an IPA was in their hands. In Milwaukee, it’s all one happy place, as it should be. A few favorite spots to have a pint as the kids play: Koz’s Mini Bowl on the South Side, and Estabrook Beer Garden up north.


The disruptive, tech-heavy last decade was not kind to local newspapers or independent bookstores. But Milwaukee has hung tough and weathered the storms much better than most cities of its size. The Journal Sentinel still has a full-time Washington correspondent, two reporters at the Capitol and a leaner-but-still fearsome crew of local reporters who tell good stories and dish out First Amendment justice to scoundrels and frauds. Bias alert: one of those reporters happens to be my wife. Having lived a bunch of bigger places, I’m regularly surprised at the quality and depth of the journalism on my front porch every morning. And Boswell Books has few peers. Someone forgot to share the memo with them about the vanishing indie bookstore in the age of Amazon.  

Dan Simmons is a contributor to our January 2018 issue, writing feature story “We Have Arrived at 35.”