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Winter Park Sidewalk Art Festival

Artist painting on canvas outdoors

After days of shopping and standing in the queue for theme park rides, you’re probably ready to see another side of Orlando. Not far from the tourist district on International Drive is the charming city of Winter Park, home to brick-paved streets, a free rose garden, and the Winter Park Sidewalk Art Festival. The popular festival, now in its 61st year, takes place on March 20-22 this year. It’s the perfect opportunity to take a break from the busy I-Drive area and admire some art. Here’s a peek at what to expect at the Winter Park Sidewalk Art Festival this year.

Admire Local Orlando Artwork

The Winter Park Sidewalk Art festival is one of the oldest and most prestigious art festivals. It’s a juried art contest, which means participating artists have the chance to earn prizes for their work. Artists will compete for 63 awards totaling $74,500, many of which are sponsored by local foundations. The best of show winner will receive $12,000 and will have their artwork placed on permanent display at the winter Park Public Library.

All artists must apply to be part of the show. If selected, they can display art in the following categories:

  • Clay
  • Digital art
  • Drawings & pastels
  • Fiber-glass
  • Graphics & printmaking
  • Jewelry
  • Leather
  • Metal
  • Mixed media 2D
  • Mixed media 3D
  • Painting
  • Photography
  • Sculpture
  • Watercolor
  • Wood

In addition to the above categories, there is also a special category for Emerging Artists. The festival’s emerging artist program allows new artists to participate in the contest at no cost. Although the selected Emerging Artists are not eligible for prizes, they receive plenty of exposure and experience. Please visit the Winter Park Sidewalk Art Festival website for more information on this year’s Emerging Artists.

Dine and Dance

In addition to admiring the artwork, you can also enjoy performances by local musicians. Concerts will take place each day of the festival, and will feature some of the best Orlando performers. The lineup will be announced closer to the festival, so check their website for more information as the day approaches.

If you get hungry, there’s no need to leave the event early. Concessions are available for purchase at the festival. If you’d rather have a more formal meal, feel free to wander around downtown historic Winter Park and enjoy delicious restaurants such as Umi, which serves up inventive Japanese fusion cuisine, and Boca, which features farm-to-table fare.

Entertainment for kids

The festival is a family-friendly event and offers entertainment for kids. Young artists can create their own masterpieces in the Children’s Workshop Village. The Village will have huge outdoor easels for painting from 10 a.m. – 3 p.m. on Saturday and Sunday. There are also other craft activities too. The Children’s Workshop Village is open every day of the festival, and best of all, it’s completely free.

Rosen Inn International

At Rosen Inn International, you can enjoy the convenience of being located on I-Drive and near the Interstate 4 ramp that will take you to the Winter Park Sidewalk Art Festival. Plus, you’ll also enjoy on-site amenities including heated swimming pools and an outdoor playground for the kids. To book your stay with us, call us at 407-996-1600 or click on the orange button at the top of the page.

Rosen Inn International Google Map
Rosen Inn International

Toll Free: 1-800-825-7600

Local: 407-996-1600

7600 International Drive
Orlando, FL 32819

Free Parking and Wi-Fi. No Resort Fees
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