Biking North Shore & Beyond: Q+A with Milwaukee City Lights

Based in Whitefish Bay but deeply rooted in the city's neighborhoods, Greg Smith is a cyclist, podcaster, and digital storyteller who has spent years building community connections across Milwaukee. Today, he recently launched a local newsletter, Milwaukee City Lights, to showcase what the city landscape has to offer.

In this Q+A, he talks about what it means to live in the peaceful North Shore while keeping your pulse on the pulse of the city, how a bike becomes a tool for discovery, and why Milwaukee's best experiences come to those curious enough to look beyond the surface.

You’ve planted roots in Whitefish Bay. What first drew you to the North Shore, and what keeps you here?

We moved to Whitefish Bay just before our first child was born partly because the schools are strong and the neighborhood felt safe and steady. Both of my kids went through the whole WFB school system, and my son earned his Eagle Scout badge with Troop 400, which is something we’re all proud of. What keeps me here now is the convenience of everyday life. I can hit Bruegger’s, Moxie, Kopp’s, Alioto’s, Culver’s, Trader Joe’s, or the Apple Store without thinking twice. Even with all that, I’ve never really felt like a classic “khakis and golf shirt” Whitefish Bay person. I live here, but Milwaukee is my orbit.

How does living in the North Shore shape the way you experience Milwaukee as a whole?

Living in the North Shore gives me a quiet home base, but most of my days are spent at my bike shop in The Nut Factory building, at the PodcastMKE Studio in the same building and in the neighborhoods I cover for Milwaukee City Lights. Riverwest, Bay View, Walker’s Point, Downtown, the Eastside (an Eastside resident as a child and through my early 30s I'll always consider myself an Eastsider!). Those places feel like where I actually plug into the city. Being based in the North Shore makes Milwaukee feel like something I enter intentionally instead of passively drifting through. Something like that anyway.

You’ve been deeply involved in local bike culture for years. How did cycling become such a central part of your life?

Cycling became my way of seeing the world early on and it never stopped. It’s transportation, community, creativity, and sometimes therapy. The fat-biking scene, and writing for Fat-bike.com, added another layer. Winter riding, beach riding, snow, ice, long cold adventures, all of it. The bike has taken me into neighborhoods, music venues, alleys, parks, trails, and weird corners of Milwaukee that I never would have found otherwise.

What are some of your favorite bike routes that connect the North Shore to the rest of the city?

The Oak Leaf Trail is where almost everything starts. Heading south takes me into Shorewood, the East Side, and right along the lake. The loop into Riverwest over the Marsupial Bridge always feels good. That route has food, music, art, and a different kind of energy. When I want something quiet, I ride north through Fox Point and Bayside. Residential streets, shoreline pockets, and stretches where you barely see a car.

If a North Shore family or casual rider asked you for a “starter adventure” on two wheels, where would you send them?

Depending on the rider's sense of adventure I'd probably suggest the Oak Leaf. The ride from WFB to the Art Museum is long enough and has many "exits" to explore neighborhoods, venues and the like. There are parks along the way, places to stop, and plenty to see. It’s an easy win for new riders. Those looking for a more adventurous ride around Milwaukee I'd suggest booking a tour with the folks at Milwaukee by Bike.

Do you have a favorite winter or “bad weather” ride around here that most people would never think to do but you love anyway?

Most people avoid the cold, but when we get a real winter with snow and frozen Lake Michigan shorelines, that’s my favorite time to ride. Fat-biking the trails along the Milwaukee River or early morning rides with fresh snow feel like a completely different world. Riding on the lake shore feels like I have the whole space to myself.

You’ve launched a lot of creative projects over the years. What was the moment you realized your informal “What should I do in Milwaukee this weekend?” recommendations needed to become an actual newsletter?

It happened gradually. Friends kept asking for ideas, not the typical places but spots with a bit of an underbelly feel. People visiting Milwaukee wanted suggestions and not always the tried and true places locals often suggest. Even locals want to know what they were missing. I already had years of photos, stories, and a habit of exploring. Turning all of that into a newsletter felt natural. Milwaukee City Lights grew out of the same conversations I was already having.

For someone new to Milwaukee City Lights, how do you explain what it is and who it’s for?

Milwaukee City Lights is a punk-eyed tour of the city’s venues, dives, events, and bright spots. It’s Milwaukee for people who don’t want the corporate guidebooks.

Which section is your personal favorite to put together each week, and why?

We are pretty new, but probably the venue spotlights. (I've been to every one I feature) They let me dig into a place’s personality, its history, and the small details that make it stand out. I get to pair my photography with stories that might otherwise go untold. It always surprises me how much depth Milwaukee has.

What has surprised you most since starting Milwaukee City Lights?

Again, we are just getting rolling but I think people are hungry for real connection. Milwaukee has layers, and I think readers want someone to help them peel them back.

How do your worlds of cycling, podcasting, and digital storytelling feed into the way you research and write each issue?

Cycling puts me on the ground. I ride past murals, new shops, old haunts, and interesting people. Podcasting keeps me curious and always listening for good stories. Digital storytelling ties everything together and lets me present the city in a way that feels alive. All three shape how I see Milwaukee. In fact, we will be spinning up a Milwaukee City Lights podcast very soon. After several hundred podcasts in the cycling space, I am ready to get into more storytelling and becoming more Milwaukee-centric.

For someone living in the North Shore, what’s one simple way they can start plugging into the version of the city you’re trying to highlight?

Pick a neighborhood you normally pass by and spend an hour there. The city proper gets a bad rap from people who don't live there. Sure there are some sketchy neighborhoods but those places also have some of the most vibrant life in Milwaukee. Grab a coffee, walk a few blocks, hit a venue, talk to a bartender, or catch a band. The city opens up fast when you let it.

Anything else to add?

Milwaukee rewards curiosity. Whether you’re riding a bike, exploring on foot, or reading along through the newsletter, there’s always something new waiting. I’m glad to help guide people toward the good stuff.