Old School Square in Delray Beach is hosting a weekend that feels designed specifically for people who appreciate beautiful things, fine experiences, and genuinely good company. Saturday brings a roaring 1920s Gatsby Party. Sunday brings the 5th Annual Concours d'Elegance—one of the premier automotive exhibitions in South Florida. Two completely different events, back-to-back, both happening in the same place. If you've been looking for a reason to dedicate a full weekend to something memorable, this is it.
Saturday: The Gatsby Party
The roaring '20s Gatsby Party runs from 5–8pm on Saturday, April 18th. Tickets are $75 per person or $140 for couples. The dress code is 1920s fashion, which means you actually get to dress up in a way that most events don't require anymore. There's something genuinely fun about a Gatsby-themed evening—it gives you permission to be more glamorous, more intentional with your appearance, more theatrical than a standard dinner party.
The evening includes a live 1920s fashion competition, which is perfect if you've been wanting to debut your vintage attire with an actual audience. There's a screening of The Great Gatsby film, which creates this nostalgic context for the entire evening. And here's the exclusive part: attendees get a preview of Sunday's car collection before the public show. That means you'll be walking through the Concours cars while they're being set up, seeing the 1960 Ferraris and 1920s Rolls-Royces without the Sunday crowds.
Dancing happens. There's food, there's cocktails, and the whole thing is designed to create that specific Jazz Age atmosphere that the 1920s represent. It's not stuffy. It's theatrical and fun in a way that makes you actually enjoy getting dressed up.
Sunday: The Concours d'Elegance
Sunday is the Concours d'Elegance, and admission is completely free. The show runs from 10am–4pm on April 19th, and this is one of those events where you genuinely lose track of time because there's so much to see and absorb.
The car lineup is nothing short of extraordinary. You'll see 1960 Ferraris in pristine condition—these are the cars that defined a generation of automotive passion. The 1920s Rolls-Royces are pure elegance, the kind of vehicles that exist in a different era entirely. There are Formula 1 racecars, which means high-speed machinery sitting inches from where you're standing. Vintage motorcycles. Exotic contemporary hypercars. The breadth of what's on display is genuinely staggering.
The judging panel includes Bill Warner, a legendary automotive executive and Concours judge; Barry Meguiar, the founder of Meguiar's and automotive culture icon; and Luigi Chinetti Jr., part of one of the most important automotive families in history. These aren't casual judges. They're evaluating these cars with the expertise of people who've spent entire lifetimes in automotive passion.
The Charitable Component
Both events benefit Delray first responder and youth charities. This means your money—or your time—is actually contributing to something meaningful in the community. You're not just attending an event for the experience. You're supporting the infrastructure that keeps the city running and invested in the next generation.
That charitable foundation actually elevates the whole weekend. It reframes the experience from "I'm doing something fun" to "I'm doing something fun and it's making a difference." Old School Square has become the center of these kinds of events, and that's largely because they understand how to create occasions that are genuinely meaningful.
INSIDER MOVE: If you're going to do both events, go to the Gatsby Party for the exclusive car preview and the experience of walking through the Concours without the crowds. Then return Sunday morning to see the cars with the full context of what you saw the night before. Arrive early Sunday—the best light for photographs and the deepest dive into specific cars happens in the morning before foot traffic gets heavy. Bring shade. It's April in Florida, and you'll be standing outside for hours. The premium viewing areas aren't necessary—the best cars are accessible from anywhere in the venue.
Old School Square is located in downtown Delray Beach. This weekend is the kind of thing that's happening now, that you're reading about just in time, and that will be sold out if you wait too long to commit. Whether you're a car enthusiast, a vintage fashion person, or just someone who appreciates experiences designed with actual intention, this is worth your time.
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