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Experience a curated fine art show in the beautiful historic setting of Old School Square

Discover Exceptional Art in the Heart of Downtown Delray Beach

November 7 - 8, 2026 | Old School Square Campus
Saturday, November 7 | 10 AM – 5 PM (judging 10 AM - 12 PM)
Sunday, November 8 | 10 AM – 4 PM

Spend an inspiring weekend surrounded by art, creativity and the unmistakable energy of Downtown Delray Beach. Art on the Square returns to the historic grounds of Old School Square, bringing together nearly 70 artists from across the country for a premier juried fine-art show.

Stroll beneath the palms and through the beautifully landscaped Old School Square campus as you explore an exceptional collection of original paintings, sculpture, photography, jewelry, ceramics, mixed media and more. Meet the artists, hear the stories behind their work and discover a one-of-a-kind piece that speaks to you.

With FREE admission to both Art on the Square and the Cornell Art Museum, this vibrant cultural weekend welcomes collectors, families, residents and visitors of all ages.

Come for the Art. Stay for Delray.

Art on the Square takes place in the cultural heart of one of South Florida’s most vibrant downtown destinations. Rather than a convention center or parking lot, this special fine-art show unfolds across the historic, park-like grounds of Old School Square and the Cornell Art Museum—just steps from famed Atlantic Avenue.

Before or after the show, enjoy everything Downtown Delray Beach has to offer. Meet friends for brunch, discover a new restaurant, browse distinctive shops and galleries, or simply stroll the Avenue and take in its lively atmosphere.

Visiting from outside the area? Turn Art on the Square into an art-filled getaway. With inviting hotels, celebrated restaurants, boutique shopping, beautiful beaches and an energetic downtown all within walking distance, it’s the perfect reason to spend the weekend in Delray Beach.

An Art Experience for Everyone

Art on the Square is designed for art lovers of all ages. Seasoned collectors can discover original, museum-quality work and connect directly with artists, while first-time buyers can explore a welcoming show filled with an exciting range of styles, mediums and price points.

Families can enjoy a lively Kids Zone featuring interactive activities and face painting. Local creative organizations—including Art Connect, the Creative Arts School and Urban Sketchers—will offer even more opportunities for engagement, creativity and discovery throughout the weekend.

Supporting the Next Generation of Artists

Art on the Square proudly supports emerging talent through its Emerging Artist Program. Each year, a selected up-and-coming artist receives complimentary booth space and the opportunity to exhibit alongside established professionals.

The program introduces visitors to a fresh creative voice while giving a promising artist meaningful exposure, professional experience and the opportunity to connect with collectors and the community.

Event Highlights:

· Nearly 70 juried fine artists from across the U.S.

· Emerging Artist Program, offering free booth space and first-time show support

· Artist awards in First, Second, and Third Place categories

· Live music throughout the weekend

· Gourmet Café featuring wine, beer, and artisanal bites

· Pop-up art activations across the Old School Square grounds

· Cross-promotion with the CRA Green Market

· Free admission to both the art show and the Cornell Art Museum

· Convenient paid parking in the OSS Garage and Federspiel Garage

· No street closures, ensuring easy access

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This beloved event has a proven legacy, with seven successful shows produced between 2017 and 2020 and earlier in 2026. Now returning for a second time this year under the direction of Cultural Arts Director Marusca Gatto, Art on the Square will once again bring world-class art to the heart of the community.

Come meet the artists. Experience creativity in action. Find something you love—and make a weekend of it in Downtown Delray Beach