The Kentucky Derby Takes on Wisconsin

May 20th, 2026 — Maxie’s Derby Day Party: May 2nd, 2026

I’ve been itching to photograph something really colorful & step outside of my comfort zone. Recently I watched one of my favorite film photographers (Willem Verbeeck) newest Youtube videos about photographing horse racing at an art deco track in California. It left me so inspired, wanting to photograph something like that; A place where people get together for one event and sometimes if you get lucky, they have some eclectic attire on.

One April afternoon while driving on i-94 in Milwaukee, I saw a billboard advertising a Kentucky Derby Party at a restaurant called Maxie’s; A Cajun, Creole & BBQ restaurant near State Fair Park and the baseball stadium! I knew this was my sign (quite literally). I got so excited & equally nervous; rarely do I step outside of my comfort zone and give myself permission to be as creative & free as I want and knew I had to reach out. As soon as I got home, I found an email for Maxie’s and asked if I could stop by to shoot the event and they were thrilled! Truly the best case scenario where they essentially said I could have free reign and photograph what I wanted.

Fast forward to May 2nd, the 2026 Kentucky Derby Day, I made my way over to Maxie’s and was so delighted by how much fun I had photographing this party. As a film photographer who’s very drawn to saturated colors and how people interact with one another, Maxie’s Derby Day Party was such a treat for me. So many people had such vivid & vibrant hats and outfits on with some of those people yapping & laughing with their friends, getting their raffles tickets from the Hunger Task Force volunteers, eating some of Maxie’s yummy food, and enjoying the brisk spring atmosphere that we had at Maxie’s on the Kentucky Derby Day.

Below you’ll find almost all of the photos I took at this party taken on my Contax G2 film camera.

Maxie's Derby Day Party with a man looking at my camera

As it might be a little obvious, one of my favorite colors to photograph on film is red. There’s so much depth and richness to that color on film and I truly cannot get enough of it.

Older couple smiling at my camera
Two women on the Kentucky Derby Day outside helping with their hats

With Wisconsin springs being so unpredictable and despite there being gorgeous blue skies, it was a bit chilly on Derby Day! What was cool about this event was the ability to stay outside but also go indoors in Maxie’s restaurant to immerse yourself even further with the Kentucky Derby Day and watch the event on the TV’s while sitting by the bar.

Let’s take a peek at what was going on inside the restaurant!

Heading back to the outdoors, I wanted to quickly take a minute to appreciate these 4 lovely women. Forever wishing I had a few moments to sit down and talk with them, but they were radiating so much joy and bliss all day long; I don’t think there was a moment where I didn’t see all of them smiling! Womanhood is such a beautiful thing to witness & be apart of and even more beautiful to capture.

4 women smiling at the camera on Kentucky Derby Day
4 women at the Kentucky Derby
Kentucky Derby Announcer
Kentucky Derby couple smiling at the camera
Couple smiling at the camera during the Kentucky Derby
Women smiling at my camera on the Kentucky Derby Day
Two men shaking hands and women talking on the Kentucky Derby Day Party at Maxie's

To round out the party and with 30 minutes left until the Kentucky Derby Race, there was a Best Dressed Contest! If you remember the 4 women I mentioned earlier, two of them actually ended up winning 2 of the different categories for the contests; Most Creative and Overall Best Hat!

Women smiling and laughing at my camera
Women at the Kentucky Derby Day winning a contest and laughing
People watching the Kentucky Derby at Maxie's in Milwaukee
People watching the Kentucky Derby captured on film
A dressed up couple watching the Kentucky Derby

Lesson learned here that stepping out of your comfort zone pays off in such unexpected ways. Never did I think I’d have so much fun from doing something that seemed a little bit intimidating to jump into! As a Wisconsin Wedding photographer, I don’t think this could’ve been a better opportunity for me to truly give myself permission to create what I wanted without limits & it goes to show what we’re capable of when we allow it.

Here’s to being creatively fulfilled and Golden Tempo for winning the Kentucky Derby!

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Maine Wedding at Camp Bishopswood | Summer and Brendan