If you’ve ever been to Winter Park, you know that there’s no shortage of art, culture and entertainment to explore in our vibrant community. And soon, we’ll welcome back a classic: the Winter Park Sidewalk Art Festival, one of the city’s best-loved traditions.

With a 63-year history, it’s no surprise that the festival is a perennial favorite. But it’s also earned national recognition among the best outdoor art fairs in the country – ranked #6th nationwide and #1 in the South. Every year, thousands flock to verdant Central Park to admire award-winning artwork and enjoy a weekend of fun.

At The Mayflower, we’re proud to be a longstanding patron of the Winter Park Sidewalk Art Festival (one of several ways we partner with local organizations to support the arts). And because the event takes place just a few minutes from our campus, many residents make it an annual tradition to attend – meeting new artists, browsing display pieces, and enjoying the liveliness and ambiance of the festival.

This year’s event – which takes place Friday, March 17 – Sunday, March 19, 2023 – offers plenty to look forward to:

  • Talented artists and remarkable creations. With hundreds of featured artists (selected from a worldwide pool of applicants), the Winter Park Sidewalk Art Festival is a showcase of dazzling skill and creativity across a wide variety of media: sculpture, glass, metal, wood, painting, photography and more.
  • Cuisine, entertainment, and music. The heart of the downtown area, Park Avenue comes alive during the festival. Enjoy a walk-through of the area’s elegant (and eclectic) boutiques, indoor and outdoor dining at local restaurants, or festival fare and live music in North Central Park.
  • And so much moreWhile you’re in the area, don’t forget to visit nearby sightseeing and artistic attractions. Rollins College’s idyllic campus, the Morse Museum’s world-class Tiffany collection, and the historic architecture of Casa Feliz are all within walking distance of the festival.

With so many cultural opportunities close to home, it’s no surprise Mayflower residents love to engage with the arts. Whether they’re honing their skillset through classes on oil and watercolor painting, attending a lecture on the history of opera or art, or supporting local organizations as patrons and advocates, creative pursuits are in abundant supply.

Discover the art, cuisine, culture and beauty of downtown Winter Park, and learn how you can “have it all” at The Mayflower – complete with a Life Plan that empowers you to live with more freedom, flexibility and peace of mind. Get in touch or give us a call at 407.672.1620 to plan your visit. We look forward to hearing from you!