Firsts in the Windy City: My Umbraco US Festival 2026 Recap

This fall I checked off three big firsts in one week: my first time traveling alone, my first time in Chicago, and my first ever Umbraco US Festival. I came home with new friends, a few too many stickers, and practical ideas about AI, automation, and Umbraco packages that I'm already putting to work at ProWorks. Here are some of the highlights that stuck with me.

Getting there: a solo adventure begins

I packed Monday night so I'd be ready for my Tuesday morning flight. My roommate drove me to the airport, and before I knew it I was on a direct flight to Chicago, on my own for the first time.

I landed at O'Hare around 5pm and met up with my ProWorks coworkers Jason and Mark. Together we walked to the train and rode the Blue Line into the city to our hotel, the Hampton Inn near the conference venue at 800 Fulton Market.

The festival started before we even reached our rooms. We were already meeting other attendees in the hotel lobby. After a quick check-in, we got ready and headed out to the pre-party.

Kicking things off at Haymarket

The official kickoff was Tuesday evening, September 29, at Haymarket Pub & Brewery, just two blocks from the venue. It's a big, loud West Loop brewpub that makes its own beer, and it was easy to meet people there. Over dinner and drinks I met a few faces I'd keep running into, and connecting with, all week. Then it was back to the hotel to set our alarms for day one.

Day one: name badges, stickers, and AI workflows

I was up at 7:30 Wednesday morning, grabbed breakfast downstairs at 8, and walked over to the venue with my coworkers. At check-in we got name badges showing our names and the companies we were attending with. There was also a table of stickers to choose from, and of course I grabbed a few for myself. Every attendee also got a raffle ticket for prize drawings throughout the conference.

We explored the second floor first and ran into some of my coworkers' Umbraco friends. I met people from partner agencies all over the country and loved hearing where they were based and what they work on. Around 9 we headed up to the 18th floor, where Karla Santi, CEO of Blend Interactive, welcomed everyone and officially opened the festival.

The full lineup is on the festival schedule.

Here are the sessions I chose for day one:

• Intentionally Building Community Through Ritual with Jason Wodicka
• Beyond the Chatbot: Building Extensible AI Workflows in Umbraco with Alex Vilmur, a hands-on afternoon that ran across two back-to-back sessions

Why rituals make Umbraco feel like home

Jason Wodicka's talk explored why Umbraco is such a welcoming community, and how Umbraco sets the example through the way it handles things. A big part of that is ritual: shared habits that give Umbracians the feeling of belonging to something.

To prove the point, we started a ritual of our own. We stood up, high fived the neighbor on one side, then the neighbor on the other, then high fived ourselves and said "We rock!" We repeated it several times during the talk until we no longer needed instructions. Something good would happen, and the whole room would just do it.

It reminded me of the rituals we already use at work. When a teammate does something we all want to recognize, we give them a #H5YR (High Five You Rock!). It isn't just a ProWorks thing, either. Umbraco partners everywhere use it. Rituals like this help everyone feel part of something bigger than a team of coworkers, and they're a big reason I've found people I can learn from and enjoy being around, whether things are serious or goofy.

Hands-on with AI workflows

Alex Vilmur's afternoon workshop, Beyond the Chatbot, was all about building AI workflows in Umbraco using the new Umbraco Automate tool. I teamed up with my co-worker Mark Bowser, and we followed along together on his laptop. Since we had the workshop materials, I later set everything up on my own device and kept building on what we made that afternoon.

During the workshop, we got to build two workflows using Umbraco Automate:

1. Podcast Production: When a podcast episode is saved, Automate grabs the content and sends it to an AI agent (our Podcast Producer) to do its thing. We added a condition so it only runs when the episode has an audio file, plus a handy setting to prevent the agent's own changes from triggering the workflow all over again.

2. Podcast Notification: Once the podcast is produced, a custom trigger we built in C# kicks off another workflow to notify the editor. This replaced the notification we'd previously handled directly in code.

It was pretty cool seeing how much of the process we could handle with Automate without code, while still being able to jump into C# when we needed something custom!

My biggest takeaway: AI is an amazing tool, and it's up to us to train it to help us, not replace us.

Tacos, a conga line, and the best trivia twist

Wednesday night was the Umbraco-hosted dinner at Carnivale Chicago, new to the festival this year and home to the first ever Umbraco US Awards.

First, the food: the chicken tacos were some of the best I've ever had. We dressed up in scarves and glasses, and I got my favorite photo of the trip with Jen Wolke, one of my tech leads at ProWorks, who also spoke at the festival with her talk Cooking Up Quality with Chef Claude. A group of dancers performed and started a conga line, and soon people were jumping in on their own. It was so much fun.

At my table I sat with Umbraco's COO and Head of Developer Relations. The evening included trivia rounds on Umbraco history and facts, naming the show a song came from, guessing idioms from a mime, and more. Each table played as a team.

When the Umbraco history round asked when the latest major version was released, we figured having the COO at our table would give us an edge. We got it wrong. Our table and the one next to us could not stop laughing.

We didn't win, but we didn't lose either, and that turned out to matter. Two teams tied for last place, so a tiebreaker question decided the single losing team. They were handed fedoras to wear while everyone laughed along. Then someone ran up to the front to announce that the losing team had also won free tickets to the next Codegarden in Copenhagen, Denmark! The room went wild.

A win for ProWorks

The night got even better during the awards. ProWorks received the Stars, Stripes & AI Award for our work with Mold Inspection Sciences! Our team accepted the award together, and we took a photo with everyone from ProWorks and the client team who attended the conference. What a win. Being part of the team behind this award was amazing.

The Stars, Stripes & AI Award recognizes projects that use AI in practical, creative ways. For Mold Inspection Sciences, publishing a new page now takes under 10 minutes of human time, traffic is up 80% year over year, and the site's accessibility score went from 86 to 98. The full story is in our Mold Inspection Sciences case study.

After the awards, we wrapped up the night with desserts and drinks, then headed back to the hotel for a good night's rest.

Day two: what even is a CMS anymore?

Day two was packed with sessions, and a clear theme ran through almost all of them: how AI is changing the way we build, sell, and use a CMS. Here's what I attended:

• Content for Humans, Content for Agents: What Even Is a CMS Anymore? with Filip Bech-Larsen, Scott Wintheiser, Nicole Rogers, and Heather Floyd
• Keynote: AI, Your Way: Umbraco AI, Community Packages and Lessons From the Trenches with Frédéric Harper and our own Jason Prothero
• Winning Enterprise Platform Evaluations in the Age of AI with Chris Osterhout
• From Brief to Build: An AI Workflow for the Non-Developers on Your Umbraco Project with Paul Marden and Chris Osterhout
• From Marketing Site to Mission-Critical Platform: A Real-World Umbraco Case Study with Stacy Hannemann and Camie Grabowski
• Practical Automation with Umbraco Automate with Joe Kepley

From keynote to my first package

The keynote, AI, Your Way, covered Umbraco AI and community packages, and it left me wanting to do more with AI. It pushed me to finally start on something I'd been asked to build: a recreation of the Matrix package. I recreated the Matrix property editor for modern Umbraco so teams migrating older Umbraco 7 sites can preserve structured content workflows without rebuilding every field pattern from scratch. With AI as a tool, I had a first working version in about three days.

I'm finishing it up now, and I'll add a link here when it's released. I'd love feedback from anyone migrating Umbraco 7 sites. This is my first package, but it won't be my last.

It's based on the original Umbraco 7 Matrix property editor by Tim Geyssens.

Lunch deserves a mention too: my first Chicago hot dog. We were warned that Chicago-style dogs skip the ketchup, and that locals would frown at us if we asked for it. I didn't risk it.

The closing party, and Chicago after dark

The official closing party was at Bandit, hosted by Blend Interactive. It was a chance to slow down and get to know people a little better. I finally got to sit down with Karla, and we talked about where she's from and which football teams she cheers for.

I called it an early night around 6, because I had one more adventure planned. My uncle lives in Chicago and wanted to show me around. In one evening we explored Chinatown, I ate my first real deep dish pizza, and I tried a merlot, which was an experience all on its own. It was the perfect way to see a different side of the city.

What I'm bringing home

The fun was real, but so was the learning. These are the ideas I'm carrying back to my work at ProWorks:

• Umbraco Automate is worth a closer look. Joe Kepley's session showed how much practical automation is possible inside Umbraco, and I left wanting to dig into Umbraco Automate and learn more.
• AI is a tool for building better packages. The keynote pushed me to build my first package, a Matrix package, with AI's help. I'm excited to keep using AI to create more Umbraco packages and move faster on ideas.
• Sell solutions, not just products and services. I wasn't supposed to be at the Partner Summit fireside chat with Umbraco management, but it ran long and I got to listen in on the closing. One idea stuck with me: clients care about the problem we solve, not the tools we use. That's how I want to think about the packages I build.
• Community is built on purpose. Jason Wodicka's talk showed that rituals like #H5YR are what make the Umbraco community feel welcoming. I want to keep those rituals going with my team and across the community.

The AI sessions reminded me that sometimes the best way to understand a new tool is to get your hands dirty and try it yourself. You don't need a big project or a complicated plan. Start with one small workflow, see what AI can help with, and learn as you go. Just remember that having a person check the results is still an important part of the process.

Until next time

I went to Chicago a little nervous about traveling on my own and came home a lot more confident. Between the tacos, the conga line, the deep dish, and a week full of great sessions, it was the best first Chicago and Umbraco US Festival experience I could have asked for. I can't wait to go back next year.

Keep exploring:

• Read our Mold Inspection Sciences case study
• Learn about the Umbraco US Awards
• See the original Umbraco 7 Matrix property editor that inspired my package
• Browse the Umbraco US Festival schedule