Your In-Depth Guide to Winter Park Sidewalk Art Festival

Journey into the heart of creativity at the 2024 Winter Park Sidewalk Art Festival. It’s pure artistic indulgence awaiting you!

Step into the world of art where each turn of the sidewalk unveils another masterpiece. Marking its 65th milestone, this year’s Winter Park Sidewalk Art Festival invites you to a sensory feast.

If a passion for fine art tugs at your heartstrings, mark your calendar for the Winter Park Sidewalk Art Festival 2024. Known as one of the oldest, largest, and most prestigious outdoor art festivals in the nation, this esteemed event attracts up to 250,000 art lovers worldwide annually.

It’s hardly surprising that the festival draws a large crowd, given the eclectic mix of more than just fine art on display. This festive tradition is packed with a multitude of events to captivate every visitor, regardless of their age. From engaging workshops to captivating exhibits, the Winter Park Sidewalk Art Festival is guaranteed to offer a comprehensive and enchanting experience, be you a seasoned art aficionado or a relaxed spectator.

So come and discover the mesmerizing range of art from clay and digital art to sculpture and watercolor. Rub shoulders with fellow art enthusiasts and marvel at the creative pieces vying for this year’s top spot.

Plus, lose yourself in the captivating rhythm of live music, all while treating yourself to scrumptious bites and refreshing drinks. Allow your senses to be enveloped by art while at the Winter Park Sidewalk Art Festival 2024.

Follow along as we take a journey through the delightful details of the Winter Park Sidewalk Art Festival.

Artistry Awaits: Winter Park Sidewalk Art Festival Date

The Winter Park Sidewalk Art Festival is set to spark the city with artistic flair from March 15, 2024, to March 17, 2024.

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Setting The Scene: Winter Park Sidewalk Art Festival’s Scenic Venue

The Winter Park Sidewalk Art Festival is conveniently set in the heart of Winter Park, at 328 N Park Ave, Winter Park, FL 32789, USA.

Brush Up on Fun: Enjoy Winter Park Sidewalk Art Festival Activities

Leon Theodore Schools Exhibit

Step into the world of innovative artistry at the Leon Theodore Schools Exhibit. This dynamic display features a multitude of student artworks from the heart of Orange County. You’ll be taken aback by the sheer brilliance of their ingenuity and finesse. Make this enchanting exhibit an unmissable part of your Winter Park Sidewalk Art Festival experience.


The Winter Park Sidewalk Art Festival is a platform where creatives exhibit their artwork, vying for 64 outstanding awards that offer a staggering total of $76,500. Since 2019, the “Best of Show” boasts of a grand $12,000 purchase award. Every year, the City of Winter Park proudly becomes the permanent home for the winning masterpiece, with the artworks elegantly displayed at the Winter Park Public Library.

Furthermore, the Edyth Bush Charitable Foundation sponsors a $5,000 “Art of Philanthropy” Purchase Award, and the Charles Hosmer Morse Museum of American Art presents a $2,500 “Distinguished Work of Art” Award.

Also, adding excitement to 2023 is the $2,000 annual “Monte Livermore Celebration of Nature Award”. The festival also features 10 Awards of Excellence, each worth $2,000, 20 Awards of Distinction, each valued at $1,000, and 30 Awards of Merit each offering $500.

Live Concert

Come 2024, the much-loved Friday Night Concert makes a grand return. A stone’s throw away in the northernmost reaches of Central Park, the Winter Park Sidewalk Art Festival commemorates the undying artistic impact of none other than Jimmy Buffet.

The festivities spark into life at 5:45, spearheaded by fan favorites Landsharks. As darkness falls, expect the night to reverberate to the rhythmic beats of Michael Andrews and Swingerhead, grandly stepping into the spotlight from 7:30 onwards.

Concert Lineup

Friday, March 15

  • 3:00 pm-4:00 pm Lake Highland Hour of Darkness Jazz Lab
  • 5:30 pm-6:30 pm The Landsharks
  • 7:30 pm-9:00 pm Michael Andrew & Swingerhead

March 16, Saturday

  • 10:30 am-11:30 am Ella and The Bossa Beat
  • 12:00 pm-12:30 pm Orlando Children’s Choir
  • 1:00 pm-1:30 pm Ella and The Bossa Beat
  • 1:45pm-2:30pm Biana Pinchuk
  • 3:00 pm-4:00 pm Timicua Presents
  • 4:45 pm-6:00 pm Oak Hill Drifters

March 17, Sunday

  • 10:00 am-11:00 am Paint It Black
  • 11:30 am-12:00 pm Arts 4 All Presents James Williams
  • 12:30 pm-1:15 pm Flint Blade
  • 1:45 pm-2:45 pm Don Soledad Group
  • 3:30 pm-4:45 pm Greg Steel Band

Children’s Workshop

Allow your children to tap into their creativity at the Children’s Workshop. The venue attracts many eager young artists, especially with the much-loved easel painting sessions. Other engaging, hands-on art and kid-friendly activities are available as well, courtesy of local art centers and museums. The best part? It’s absolutely free, and your young ones can keep their masterpieces!

Make sure to plan your visit as the Children’s Workshop opens its doors from 10 a.m. to 4 p.m. on Fridays, Saturdays, and Sundays. Additionally, our easel painting sessions are hosted between 10 a.m. and 3 p.m. on Saturdays and Sundays.

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Complimentary Bike Corral

Prepare for a vibrant excursion to the Winter Park Sidewalk Art Festival. You can conveniently park your bicycle at the free Bike Corral located off Morse Boulevard, directly across from the Train Station parking lot. This thoughtful gesture is made possible by the Winter Park Pedestrian and Bicycle Advisory Board.

Food And Concessions

If your palate is adventurous and diverse, you’re in for a treat. Winter Park Sidewalk Art Festival is not just a feast for the eyes, it’s a culinary experience as well. The whole Central Park vicinity in Winter Park showcases an extensive assortment of restaurants and cafes sure to satisfy your cravings.

Winterpark Sidewalk Art Festival Tickets

Attending the event won’t cost you a penny. Yes, it is absolutely free!

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Parking Options

The Winter Park Sidewalk Art Festival has ceased its shuttle services from remote parking locations. However, that doesn’t mean parking will be an issue. Plenty of parking options can still be found around the downtown area, where you’ll be immersed in the enchantment of sidewalk art.

When it comes to parking, choices are ample on the nearby streets, most of which operate on a modest day-rate. Spearheaded primarily by commendable charitable groups like the Boy Scouts and church youth bands, these services are primarily located on avenues like Interlachen and New York.

Additionally, Rollins College, located at 1000 Holt Avenue, Winter Park, FL 32789, owns a parking garage located at the southern edge of Park Avenue. This garage is accessible to attendees of the Winter Park Sidewalk Art Festival.

Make sure to plan your visit to secure these limited availability parking spots.

Orlando Attractions

Orlando is a city that buzzes with life, pulsating with creativity and an innate spirit for the arts. Its remarkable building structures and deep-seated cultural roots fill every moment with awe-inspiring sights. Be part of an unforgettable mix of masterful art, captivating culture, and riveting entertainment as you explore these attractions:

Nearby Hotels and Lodging

Have you considered making the most of your trip to the Winter Park Sidewalk Art Festival 2024 by extending your stay in the dynamic city of Orlando? Reserving accommodation not only provides you with a haven to rejuvenate after each exhilarating day at the festival, but also gives you the chance to delve into the multitude of attractions Orlando is renowned for.

With its top-tier theme parks and alluring beaches, there is a trove of experiences waiting for you beyond the Winter Park Sidewalk Art Festival.

Dive into the Excitement of the Winter Park Sidewalk Art Festival

The Winter Park Sidewalk Art Festival is laced with an abundance of activities that would pique an art enthusiast’s interest. From clicking and appreciating the Winter Park Sidewalk Art Festival photos, to spending hours immersing yourself in the stunning display of fine art, the possibilities are endless.

It’s a smorgasbord of creativity, showcasing a delightful array of artworks spanning various genres – from traditional paintings to groundbreaking installation pieces, all set beautifully along the park’s sidewalks.

This year, the Winter Park Sidewalk Art Festival 2024 promises to surpass all expectations. Get there early, so you have the full Winter Park Sidewalk Art Festival hours to indulge in a vibrant, art-filled experience and witness art being created right before your eyes.


Start Date:

March 15, 2024 @ 9:00 am CDT

End Date:

March 17, 2024 @ 5:00 pm CDT



Orlando Events

Orlando, FL United States


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Written by Anne Joyce Raymundo

Anne is a Filipino writer who formerly managed and created marketing strategies and materials for numerous websites and eCommerce platforms. Now, her voice...

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