Festival season never really stops in Milwaukee. From January all the way through December, there’s something to celebrate, but spring is when the City of Festivals really kicks into full swing, packing almost every weekend on the calendar with a little extra excitement. In May alone, there’s a beer run, floral festivities, artistic ink, and tacos and tequila with a side of luchador wrestling. Here’s what you can expect from Milwaukee’s festival scene in May.

A woman in a floral dress and wide-brim hat sits on a bright yellow bench surrounded by a large arch of blue hydrangeas and pink flowers, holding colorful “MKE” letters. A sign nearby reads “Milwaukee Public Market Festival of Flowers,” with tents and market stalls in the background.

Festival of Flowers

Saturday, May 16 | 11 a.m. – 3 p.m.
Riverwalk Commons

The sweet scent of flowers, a gentle spring breeze and just enough shade under the cover of the Riverwalk Commons to keep you from getting too hot. It’s quintessentially spring, and one that you just have to join in. This free, one-day festival turns the urban park into a garden in full bloom, with magnificent floral displays, along with vendors selling fresh-cut flowers, flower art, plants and so much more, all to the tune of a live DJ with seasonal bites and sips on tap. This festival is spring’s unofficial launch party, and it all takes place just steps away from the Milwaukee Public Market.


5th Annual Maifest Gluten-Free Festival

Sunday, May 17 | 10 a.m. – 3 p.m.
Lakefront Brewery

Speaking of spring traditions, what was originally the German celebration of the season’s arrival is back for its fifth straight year, with far less gluten than its ancestral roots. This grain-less gathering along the Milwaukee River is a glut with gluten-free brews and bites all day long. Taking place at Lakefront Brewery, the home to the nation’s first, best-selling and best-tasting gluten-free beer, as well as the CurdWagon, a gluten-free beer truck, the local brewing behemoth has a full day all lined up in Lakefront Lane. There’s live music, pints and pints of gluten-free beer, and heavenly, celiac-friendly bites like grilled burgers and sausages, soft pretzels, BBQ-flavored cheese curds, Cheez-It-crusted chicken tenders, and Thai PB&J-fried brussels sprouts. All for free and gluten-free!

Aerial view of a large outdoor festival with a carnival setup, including rides, food stands, and game booths arranged in a park. A large white event tent is filled with people in the foreground, with lines of parked cars and crowds gathering around it. Pathways, green lawns, and nearby buildings surround the event, with busy streets and additional parking visible along the edges.

Dan Jansen Family Fest

May 22-24 | Konkel Park

Spring skates by faster than you think. Don’t let it pass you by. Pack up the fam and soak up a little springtime fun at the Dan Jansen Family Fest in Greenfield. More than 20 years before Jordan Stolz raced his way to a gold medal, local speedskater Dan Jansen etched Wisconsin’s name in the Olympic storybook, earning gold in the 1994 Games. It was such an achievement that the Greenfield community named a park after him, home to an ice skating rink, and now a four-day festival. Taking place over four days in May, this festival has a little bit of everything. Food, live music, cheer performances, yoga and even a car show? Yeah, this is one you’re going to want to see for yourself.

 

Milwaukee Tattoo Festival

May 29-31 | Baird Center

Milwaukee is a city that celebrates art in its many forms. There’s floral arrangements of Art in Bloom in April, the sheer energy of live music at Summerfest in June and July, and smack-dab in the middle of it all is the Milwaukee Tattoo Festival. Each tattoo tells a story. Some deeply meaningful, others almost intentionally meaningless; it’s one of the most personal forms of art that sometimes literally puts a heart on your sleeve. I’ll let that sink in. The Milwaukee Tattoo Festival brings more than 400 tattoo artists together for a weekend of ink, art and attitude. Creativity takes center stage with live tattooing, jaw-dropping sideshows and contests that prove tattoos really are forever. Think ink and find your next masterpiece.

A performer in a red hoodie stands on an outdoor stage facing a massive crowd at sunset. Thousands of fans pack the venue, many holding up phones to capture the moment, while bright stadium lights and food stand signs glow in the background.

Tacos & Tequila Festival

Saturday, May 30 | 2 p.m. – Midnight
Franklin Field

Yeah, taco Tuesdays are cool, but tacos and tequila are a pairing so iconic that they deserve their own festival, and lucky for you, it’s right in our own backyard. Each year, the Tacos & Tequila Festival grows just a little bit more, becoming a staple that draws big crowds to the turf of Franklin Field. And with big-name headliners, luchador wrestling matches, a Chihuahua beauty pageant…I repeat a Chihuahua beauty pageant and, of course, tastes of tacos and tequila, it’s no surprise. This year, the festival boasts a lineup of Shaggy, Rick Ross and Soulja Boy, busting out the hits and bringing down the house when the sun goes down.


BikerFest Block Party 2026

Saturday, May 30 |  Noon – 9 p.m.
East Side Neighborhood

As the birthplace of Harley-Davidson Motorcycles, Milwaukee’s got motoculture rumbling through its veins, and this festival is the perfect place to rev up to the warmer weather. The BikerFest Block Party is roaring to life on the city’s East Side in May for a one-day fest that roars with activities for the whole family. This community-powered block party is where everyone is welcome, with unity at the heart of it. And motorcycles. So many motorcycles. Don’t miss out on this feel-good day filled with music, food, fun and plenty to do for everyone.


Morning Glory Art Fair

May 30-31 | Marcus Performing Arts Center

A traveling local art exhibit is coming to the Marcus Performing Arts Center to close out the month, and you can take a piece of it home with you at the Morning Glory Art Fair. Taking place over two days, you’ll uncover breathtaking artistic expressions from just about every discipline, from textile and apparel to painting and decorative arts to jewelry, and so much more. You’ll find eco-inspired lamps made from found tree branches, ceramic works so unbelievably detailed that you’ll swear they’re alive and landscape paintings so vivid that you can smell the fresh sea air on a warm summer’s day. Each work is available for purchase, so when a piece speaks to you with the voice of inspiration, you can add it to your own collection.
 

A crowded street festival stretches down a tree-lined residential block, with vendor tents on both sides and large groups of people walking and browsing. Many attendees wear matching “Locust Street Beer Run” shirts and race bibs, mingling among booths selling clothing, food, and drinks.

Locust Street Festival of Music & Art

Sunday, May 31 | 11:30 a.m. – 8 p.m.
Riverwest Neighborhood

If you’ve ever thought about buying a bumper sticker that reads, “Will Run for Beer,” our last fest of the month is for you. Dating back over 47 years, the Locust Street Festival of Music & Art has brought the pre-summer fest vibes to the Riverwest neighborhood with a big block party. It’s got four stages, packed full of live music, tons of local vendors and plenty to sip and savor as you bask in Milwaukee’s peak spring weather. The headliner of this one, though, has to be the Locust Street Beer Run, a high-ABV run/walk that’s so quick, you might miss it if you blink. It’s a casual, 1.6-mile course that’s as much a rite of passage as it is an athletic endeavor. To make it worth your while, the course is ditching the Gatorade, bailing on the bananas and eschewing the gel packs in favor of four delicious Riverwest brews, leaving you feeling no pain at the finish line.

 

There’s always something to celebrate in the City of Festivals! Find your fest, plan your getaway and book your stay today.