2016 Winter Park Art Festival on March 18th, 19th, and 20th in the Spring is the Best Annual Art Festival in Orlando

© Orlando Local Guide
© Orlando Local Guide

Orlando is very fortunate to have several premium art festivals throughout the year to attend and browse great art with the Festival of the Masters at Downtown Disney and the Fiesta in the Park Festival at Lake Eola in Downtown Orlando in the Fall.

The Mount Dora Arts Festival is a major art festival that is held during the first weekend in February each year during the spring time and attracts several hundred thousand visitors.

However, as great as these art festivals are, when needing to crown the best annual art festival in the city of Orlando to one particular festival, Orlando Local Guide gives the award to the Winter Park Sidewalk Art Festival in Winter Park, Florida that is held on the streets and park of Park Avenue and Central Park each spring.

Winter Park Sidewalk Art Festival 2016

The Winter Park Sidewalk Art Festival, one of two major art festivals that Winter Park holds each year with the other being the Autumn Art Festival in the fall, will be held on Friday, March 18th, 2016 through Sunday, March 20th, 2016 along Park Avenue within Central Park. Now in it’s 57th year, the Winter Park festival is one of biggest local events that really brings the entire city of Orlando together. In fact, some 350,000 visitors from the Central Florida area will be in Winter Park during the weekend to attend the show to check out the 225 vendors that were selected out of the 1,200 applications that were received.

Art on Display

There are many type of categories and types of art on display at the festival all grouped in different sections in Winter Park including Clay, Digital Art, Emerging Artists, Drawing and Graphics, Fiber, Glass, Jewelry, Leather, Metal, Mixed Media, Painting, Photography, Sculpture, Watercolor, and Wood. Click on the links of the different categories above to preview the displays that will be shown during the festival. Some of the most popular works are the larger sculptures that are displayed on the green.

Competition and Prize Money

For the 2016 festival, there were 62 individual awards given out at the Sidewalk Art Festival with the Best of Show receiving a $10,000 award. The total amount of all awards handed out equaled out to be $67,500. The Winter Park Sidewalk Art Festival Committee purchases the Best of Show piece of art and donates it to the City of Winter Park. All previous Best of Show winners are on permanent display at the Winter Park Public Library.

Music and Entertainment

Throughout the festival, different bands and musical acts play in the park on stage that feature brass, jazz, a capella, and children’s music. The 2016 entertainment lineup is TBA, but the 2013 entertainment was:


8:00 am Production Set Up
4:30 pm – 5:15 pm Beautiful Music Jazz Ensemble
5:45 pm – 7:00 pm Matt Shenk Band
7:30 pm – 9:00 pm Steve Cole


10:00 am – 10:45 am Paint it Black Quartet
11:00 am – 11:45 am Rollins Brass Quintet
12:00 pm – 12:45 pm Suzuki Institute
1:15 pm – 2:15 pm Pop Shop
2:30 pm – 3:30 pm Rich Walker Trio
4:15 pm – 5:45 pm Brian Simpson


10:00 am – 10:45 am Three Flutes Only
11:15 am – 12:15 pm Rollins Acoustic Ensemble
12:30 pm – 1:30 pm MakeShift
1:45 pm – 2:15 pm Bailey Callahan
2:30 pm – 3:00 pm Angela and the Gazebros
3:30 pm – 4:30 pm Jeff Kashiwa

Children’s Workshop Village

In addition to the great art and music on display for the adults, the festival also has a lot of free activities for the kids to get involved with as far as creating their own works of art and crafts with easel painting at the Children’s Workshop Village.

Where to Eat

The festival has your typical festival vendors to get a quick bite to eat but there are also a lot of great restaurants along Park Avenue to choose from that spill out into the street during the festival weekend. Some of the restaurants to consider that are all around the intersection of Park Avenue and New England are Luma on Park, 310 Park South, Prato, Boca, and Park Plaza Gardens.

Click Here to view Orlando Local Guide’s Top 10 Romantic Restaurants in Winter Park to choose from that also make great choices for dining.

Where to Stay

Your best bet for lodging during the weekend (if you can get it) is at the Alfond Inn across the street from Rollins College and Park Plaza Hotel on Park Avenue that is right there within all of the action. The Best Western Mt Vernon Inn recently closed in 2014 and is no longer an available option.

Event Information

The Winter Park Sidewalk Art Festival will be held from 9 AM – 6 PM on Friday and Saturday and 9 AM – 5 PM on Sunday. Click Here to view the official website for the event.

Click Here to view Orlando Local Guide’s complete coverage of the City of Winter Park.

Click Here to read about other art festivals taking place in and around Orlando throughout the year.

2013 Winter Park Sidewalk Art Festival Video

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