As Woodlawn Arts Academy marks two decades of impact, this year’s fundraiser carries extra significance. Events like these are not just social gatherings; they are essential to sustaining the organization’s mission. With roughly a third of its budget supported by fundraisers, donations, and grants, community participation plays a vital role in ensuring that classes, performances, and creative programming continue to thrive.
The Winner’s Circle Fundraiser builds on the success of last year’s Kentucky Derby–inspired event, bringing back the high-energy theme with even more to offer. Guests are encouraged to embrace the spirit of the Derby, dressing in festive attire while enjoying an evening designed to keep everyone engaged. Admission includes a spread of heavy hors d’oeuvres, creating a full and satisfying experience while attendees mingle and explore the event.
Throughout the night, there will be a wide variety of activities that go far beyond a traditional sit-down fundraiser. A silent auction featuring curated baskets, a 50/50 raffle, and a lively dessert dash all add to the excitement. This year also introduces a brand-new feature—the Art Dash—where participants can secure the chance to claim original artwork donated by local artists. With only a limited number of spots available, it brings a competitive and memorable twist to supporting the arts.
The event will also feature interactive games inspired by horse racing, including opportunities for participants to win prizes based on race outcomes. Music, themed photo opportunities, and a vibrant atmosphere ensure that guests remain active and entertained from start to finish.
In addition to the festivities, the evening will mark the launch of Woodlawn’s summer art exhibit. This special showcase highlights 20 years of programming, offering a visual journey through the academy’s history. For those who have been part of the Woodlawn community—whether as students, artists, or supporters—it’s a meaningful way to reflect on the organization’s lasting impact.
There are also hints of a few surprises in store, with playful elements that add even more personality to the event. The goal is to create an experience that feels fun, immersive, and uniquely tied to the arts.
The Winner’s Circle Fundraiser takes place on Friday, May 1, from 6 p.m. to 10 p.m., aligning with Kentucky Derby weekend festivities. Tickets are $50 and can be purchased at Woodlawn Arts Academy during regular business hours. A limited number of Art Dash opportunities are also available for those looking to take part in that special experience.
Beyond attendance, local businesses are encouraged to get involved through sponsorships, helping to support the academy while gaining visibility within the community. These partnerships are a key part of what allows Woodlawn to continue expanding its reach and offerings.
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