Cultural Events in Delray Beach, FL

If you're considering a move to Delray Beach or simply want to enjoy the area like a local, one thing becomes clear quickly: this town knows how to celebrate. With sunshine nearly every day and a deep appreciation for the arts, food, music, and community, Delray Beach offers a packed calendar of seasonal events that reflect its personality.

From farmers markets and art walks to block-long dinners under the stars, these cultural happenings are what make this city feel like home.

Every Saturday morning during the season, Old School Square transforms into the heart of the community. The Delray Beach GreenMarket has become a weekend tradition, running October through May, and even extending into June and July with a smaller summer series. More than 65 vendors gather weekly to offer fresh produce, local honey, artisan breads, seafood, orchids, and handcrafted goods.

But it’s more than just shopping. You'll hear live music, see yoga on the lawn, and spot neighbors catching up over fresh-pressed juice or a bag of warm empanadas. Whether you’re walking the dog, grabbing ingredients for brunch, or just soaking in the morning sun, the GreenMarket is one of the most beloved Saturday rituals in Delray Beach.

Savor the Avenue is one of Delray’s most iconic annual events, and for good reason. For one unforgettable night in March, Atlantic Avenue closes to traffic and transforms into a five-block-long communal dining table. Over 1,000 guests gather to enjoy multi-course meals from Delray’s top restaurants, like The Grove, El Camino, and Lionfish, each curating a custom menu and tablescape.

This event is equal parts culinary and creative. It's elegant yet relaxed, and completely unique to Delray Beach. If you're looking to experience the city’s food scene at its most inspired, this is the night to mark on your calendar.

For fans of sports, the Delray Beach Open brings ATP tennis right into the city’s backyard. Held at the Delray Beach Stadium & Tennis Center, this 10-day event features top-ranked international players, and it’s not just about the matches.

There are happy hour tents, pop-up lounges, and local vendors on-site, creating a social scene that goes beyond the court. Whether you're a die-hard tennis fan or just want to enjoy a high-energy event in beautiful weather, it’s a major highlight of the season.

When spring rolls in, so does one of the largest arts and crafts festivals in the Southeast: the Delray Affair. Spanning 12 blocks of Atlantic Avenue, this multi-day event attracts artists, artisans, and visitors from around the country. You’ll find everything from handmade jewelry and global textiles to original paintings, photography, and gourmet treats.

It’s more than a shopping experience; live music, food trucks, and a festive, outdoor atmosphere make it a weekend-long celebration of creativity and community. For new residents, it's also a great way to discover local businesses and meet neighbors.

While technically held in West Palm Beach, this event draws plenty of attention from Delray locals, especially those with a love for the water. The Palm Beach International Boat Show is one of the country’s premier yachting showcases, featuring hundreds of vessels from fishing boats to luxury superyachts.

Beyond the boats, the show offers live demos, a VIP lounge, and marine seminars. For many Delray residents, it’s a short drive and a must-attend event that reflects the region’s upscale, outdoor lifestyle.

This recurring event turns Atlantic Avenue into a street party with a creative twist. Hosted on select evenings, Art & Jazz on the Avenue features live jazz, pop-up art galleries, performance artists, food vendors, and open-air shopping. Local businesses stay open late, and the atmosphere is lively but casual, perfect for a stroll, a cocktail, and a taste of Delray’s artistic side.

Whether you’re a long-time resident or just moved in, it’s an easy way to connect with the creative pulse of the community.

Delray Beach’s holiday season is a special time. The city’s 100-foot Christmas tree in Old School Square is a showstopper, lit up in early December and surrounded by activities for kids and families. Inside the tree? A walk-through display complete with themed holiday scenes.

New Year’s Eve brings First Night, a family-friendly celebration filled with street performances, food vendors, and fireworks. These festive traditions are especially meaningful for new homeowners, creating opportunities to gather with neighbors and make lasting memories.

When people explore events in Delray Beach, they’re often surprised by the sheer variety and quality of what’s offered. But for locals, it’s just part of life here. These events bring the community together, support local businesses, and add depth and joy to day-to-day living.

Whether you're hosting out-of-town guests during Savor the Avenue, spending Saturday mornings at the GreenMarket, or watching fireworks with your family on First Night, Delray’s seasonal events help you feel rooted in a place that celebrates connection and creativity.

If you're dreaming of a lifestyle that blends walkability, sunshine, and a true sense of community, Delray Beach delivers. And when you're ready to explore homes in the area, it's important to work with someone who knows the rhythms of the neighborhood; not just where to buy, but when to catch the next great local event.

Lisa Wennick brings deep local knowledge, a passion for Delray living, and a personalized approach to every client. Whether you're moving from across the country or across the street, she’s ready to help you find a home that fits your lifestyle and puts you close to everything that makes Delray Beach unforgettable.