If you’ve ever wandered into Vagabond and thought, “Wait… how is this place not talked about more?”—you’re not alone. Tucked away but impossible to forget, Vagabond has quietly built a reputation as one of Milwaukee’s hidden gems, where street tacos, house-made margaritas, and eclectic design collide.
The space was reimagined in 2015 into what Vagabond is today: a one-of-a-kind spot that feels more like a destination than just another dinner stop. Backed by the Water Street Brewery Group and deeply rooted in Milwaukee’s service industry community, Vagabond has stayed true to its culture while constantly finding new ways to evolve—from creative collaborations to meaningful giveback initiatives.
We sat down with Kelley Cramer, Digital Media and Marketing Manager, to talk about Vagabond’s origin story, what it’s really like running a bar and restaurant in MKE, their Taco of the Month partnerships (including a familiar collab 👀), and why supporting the city is baked into everything they do.
How did Vagabond get its start? What is your background?
It was originally Rudy’s Mexican Restaurant and decided to give the space a fresh new look. I started with the company in 2017 and am now the Digital Media and Marketing Director. The Water Street Brewery Group owns Vagabond, the Harp, Trinity Three Irish Pubs, the Brewery in downtown Milwaukee and three Water Street Brewery locations in Delafield, Oak Creek and Grafton.
How long have you been in business? Have you faced any major challenges with growing your business or any triumph stories?
Vagabond opened in 2015. Running a bar/restaurant always has it’s challenges but that’s what makes us better! We’ve had to pivot over the years on some things, but have remained consistent with our brand, food and culture. We participate in Do Good with Food every year to benefit Children’s hospital. Since its inception in 2019, the event has raised more than
$206,000 for kids and families.
What is Vagabond, and why did you feel it would be a good fit in Milwaukee?
The concept was to serve street tacos and a variety of small plates combined with fresh, house-made margaritas to make for a unique one-of-a-kind dining experience. The bar and aesthetic itself is worth the trip in for a visit!
What’s the mission behind Vagabond?
Aiming to provide the best service and food quality we can! We also are big on supporting the City of Milwaukee, which is why we came up with the Taco of the Month Partnership in 2019. Every month we find a new local business, artist or groups to collaborate and cross promote with!
We started with MODA3 and have paired up with KOSS, the Admirals, Britt Musial (great local artist), the Moderne and the list goes on! Including our collab last year with Milwaukee Uncut Podcast!
What is it like being a small business in MKE?
It’s such a great way to get to know people and watch how the city has grown in the last 10 years.
What do you like about being in Milwaukee?
It’s one big family in Milwaukee. Especially the service industry. We all have eachothers backs through the ups and downs.
What’s your favorite part about what you’re doing?
I love being creative with promotions and teaming up with a new company in the city every month. We chose MADACC for December and January because we wanted to give back and help out a local charity. I rescued a dog 9 years ago and a lot of our staff are animal lovers so it’s a blessing to be able to donate!
What can people expect when going to Vagabond?
You can expect the best hidden gem in the city. The moment you walk through the doors it’s like you’re transported to a new world. Local art, fresh food, house made margaritas and more!
Anything else we should know about your business or anything you’d like to mention? Any favorite stories?
We just want to let the city know we’re always cooking up something new and aim to make the customer happy. One of my favorite stories is having Charlie Berens shoot some footage in our airstream bar, knowing that the night before the staff had a fun game of hide and seek after we closed (totally responsible) and my buddy fell asleep on top of the airstream he was in.