You've been to art galleries. You've nodded knowingly in front of paintings you only partially understood. You've maybe even bought a print or two. But have you ever watched a painting happen? Watched an artist stare down a blank canvas, brush in hand, clock ticking and then seen something extraordinary appear out of nothing in front of your eyes? 
 

That's ART 64, and it's coming back to the streets of Wauwatosa on June 5 and 6. For the uninitiated, ART 64 is the nation's largest bracket-style painting tournament. Sixty-four artists compete live, on a timer, in front of your eyes, across two days of rounds. And you vote to advance your favorites for their chance to take home the ART 64 title, along with a $20,000 grand prize. 
 

Here's how to do it right. 

Date Night in the Village 

Friday, June 5 | 5-8 p.m. 

Leave the kids at home for this one. Round 1 kicks off Friday evening, and the Village is basically begging you to make a night of it. 
 

Start at The Ruby Tap for drinks on the patio. Order a wine you've never tried before, get a cheeseboard and relax on the patio while the evening settles in around you.  

From there, follow the music. Live performances are programmed as part of It's Alive! Milwaukee on the Wire and Vice Stage presented by Milwaukee Theater District.  

Artists are painting live on the streets around you, 60 minutes on the clock, and the air carries that particular mix of paint and possibility you didn't know you'd been missing. Stand close enough to see the brushstrokes. Grab a local brew and cast your vote for who moves on to Saturday. 

For dinner, you’ll find no shortage of tasty bites in the Village. Now’s the time to branch out and try something new. For dinner with views of all the ART 64 action, look no further than Ristorante Bartolotta dal 1993 for fine Italian fare, Leff's Lucky Town for classic wings and bar bites or Buckatabon Tavern & Supper Club for a North Woods supper club experience.  

Family Day 

Saturday, June 6 | 10 a.m. - 4:30 p.m. 

Round 2 starts at 10 a.m. The Finals fire up at 1:30 p.m., and the winner is announced at 4:30 p.m. That's a full day. Here's how to pace it. 
 

Morning: Free Kid Programming 

The North Shore Bank Family Fun Zone is completely free, face painting, bubbles, crafting stations, all of it. Let the kids loose while you grab a coffee from Vendetta or Anodyne and enjoy a few quiet sips before the chaos resumes. Save your cash; you'll want it later. 
 

Once they've worked through every station (maybe even twice), walk the streets of ART 64. Watch an artist lay down color on a canvas. Kids, it turns out, are often the most opinionated voters, with very specific interests and very strong takes. 

Midday: Cross the River 

Head over to Hart Park for a picnic. Pack something from home or grab bites from the Village or Outpost Natural Foods and enjoy the fact that summer is here, you are outside, and there is nowhere you need to be right now. Bonus: the park recently added community pickleball courts. Get in a quick volley before returning to the action. 
 

Afternoon: Rally and Return 

Head back for the Finals at 1:30 p.m.  Ninety minutes, one theme, the best artists left standing. Don't miss Unfinished Legacy's live silkscreen station, create your own limited-edition wearable art on the spot. Keep shopping and strolling in between, and when the kids start to fade (they will, we promise), you've got two very good options. 

Niemann's Homemade Candies & Ice Cream has been making everything from scratch since 1919, and one bite will prove it. If your crew skews more customizable, Yo Mama serves froyo with a full toppings bar, basically the perfect democratic dessert for a family that can't agree on anything.  

No kids in tow? Pull up a stool at Draft & Vessel for a craft brew or cocktail and extend the afternoon. 

Be back in the Village for the winner announcement at 4:30 p.m. After the big reveal, keep the evening going, grab a slice at Maggio's Wood Fired Pizza or settle in at the beer garden at The Landing at Hoyt Park Beer Garden, then catch a film at the Rosebud Cinema to keep your art-and-culture crawl going. 

Explore More at ART 64

Craft your own ART 64 masterpiece. Find your inspiration, map your visit and discover that your artistic getaway is just a few clicks away!