Is The Winter Park Sidewalk Art Festival Worth It?

Art lovers far and wide make the annual fall pilgrimage to Florida’s Winter Park Sidewalk Art Festival. The variety of artwork on display is a treat for the eyes.

If you’re looking for a family-friendly place to visit, Winter Park and the surrounding area have you covered.

Discover why hundreds of thousands of people attend this art festival every year. 

Let’s check it out!

What Is the Winter Park Sidewalk Art Festival?

Debuting in 1960, the Winter Park Sidewalk Art Festival showcases works from top artists worldwide. Beginning as a project for local Winter Park, Florida, craftspeople, it’s now one of the nation’s most prestigious outdoor art shows. 

Held every March, the festival offers art created by hundreds of artists worldwide. Located in the city’s Central Park, vendors set up their booths along tree-lined paths or on the adjacent streets of Park Avenue. This popular three-day event regularly draws over 300,000 people.

What Type of Art Does the Winter Park Sidewalk Art Festival Show?

Each year, around 1,000 artists submit applications for a chance to display their craft. Submissions must fall into one of 16 categories such as clay, wood, digital art, leather, printmaking, photography, and jewelry. 

Submitted works go through a three-person jury to determine who will receive a coveted invitation to the festival. Artists often apply multiple times before being accepted. 

Such was the case in 2016 for mixed-media artist Margaret Luttrell from Tennessee. Luttrell applied three times before being invited. “I had to read it twice when I got the acceptance, I was so excited.”

The lucky artists chosen to be part of the festival compete for 63 cash awards totaling over $74,000. Each year’s Best of Show winner receives $12,000. The winning artwork is given to the Winter Park Public Library for permanent display. 

Where Is the Festival?

Held in the 11-acre Central Park, the art festival is one of Winter Park’s most popular outdoor events. Located in the heart of the downtown shopping area, you’ll have many places to choose from to spend your money. 

While driving to the festival is an option, you may be better off taking alternative transportation, if possible. SunRail operates across multiple counties, offering free parking at most stations. Exiting the train at the Winter Park Station, you’re just a short walk away from the art festival. 

Additionally, the city provides free bike parking in an area across from the train station on Morse Boulevard. Limited parking spaces are available near Central Park for patrons with current ADA placards. 

How Much Does It Cost to Attend the Winter Park Art Festival?

Entrance to the festival is free for all attendees. Since there’s plenty of shopping to be done at the show and in the surrounding area, you’ll want to bring plenty of cash. And probably even credit cards for those high-end art purchases!

What Is the Foundation Behind the Festival?

The Winter Park Sidewalk Art Festival Foundation, Inc. funds local youth art programs and college scholarships. The mission of the Foundation is to enhance art appreciation, art education, and community spirit.

In addition to supporting workshops at the festival geared towards children, the Foundation also funds the Emerging Artists Program. As the name implies, the program encourages new artists to apply for a spot to sell their works at the festival. 

Participants accepted don’t pay a booth fee and aren’t eligible for cash awards. However, the exposure they receive as festival artisans is incredibly rewarding. 

Is the Winter Park Sidewalk Art Festival Good for Kids?

The kids will love coming to the festival and participating in the Children’s Workshop. They’ll be able to get their creative juices flowing by painting a picture on large easels. The young artists can bring their masterpieces home with them, too. 

Each year, over 1,000 kids participate in the workshop. For over 30 years, the Children’s Workshop has provided an outlet for young attendees to try their hand at making art. 

Is There Entertainment at the Festival?

The Winter Park Sidewalk Art Festival includes live music at a stage located on the north end of Central Park. You’ll hear lively tunes from various contemporary bands and musicians throughout the weekend. 

Additionally, a special kick-off concert takes place the weekend before the festival. If you’re in the area early, plan to attend this show to get you in the mood for the upcoming festivities. 

Does the Winter Park Festival Offer Food?

Yes, lots of options are available for filling hungry bellies. Choose from dozens of food vendors, or pick a restaurant nearby to relax and enjoy a meal. Within a short walk from the festival, you’ll find everything from a quick snack to a steak dinner. 

What Else Is There To Do Near the Festival?

Located less than ten miles from Orlando, you may want to plan for a stay extending beyond the weekend. Or try to cram as much as possible into a three-day vacation!

Whether you want to spend time indoors or out in nature, you won’t have any lack of things to do. Winter Park and the surrounding area offer several museums, gardens, and theaters. 

Outdoor enthusiasts will love the Winter Park Chain of Lakes. The six lakes connected by canals are perfect for taking a paddleboard or kayak out for the day. 

Is a Trip to the Winter Park Sidewalk Art Festival Worth It?

If you enjoy spending the weekend outside viewing and potentially buying fine art, the answer to this question is certainly yes. And if you’re a foodie, in addition to being an art lover, you’ll appreciate all the delicious offerings around this Winter Park festival. 

No matter what, if you attend this event and spend time exploring the area, you’re likely to have a great trip. 

Have you attended the Winter Park Sidewalk Art Festival? Let us know about your experience in the comments below.