Winter Park Sidewalk Art Festival

I was ecstatic to get juried into Winter Park this year for the first time. I wasn't sure what to expect but was certainly aware of the reputation that precedes this show. 

I made the trek from Tennessee on Wednesday, spent the night in Gainesville, Florida then continued onto Winter Park on Thursday for load in.  I had looked at the map of the show beforehand so knew exactly where my booth placement  in Central Park was thanks to Google Street Maps. I was directly between two massive cedar trees. Shade for the entire weekend! 

Load in was fairly straightforward. Park on Park Avenue in front of Central Park and dolly to your space. I'm really happy that I had one of the booths with a sidewalk in front as opposed to a mulch walkway. I unloaded my truck, dollied everything to my space then moved my vehicle to the grass lot on the other side of the railroad tracks. I had all afternoon to set up so it was probably one of the more casual laid back set ups. Normally set up is about 1 hour for me but I took about 4 hours with lunch at a French bistro just off Park Ave. 

Friday was a great day for me. With a forecast of upper 80s for the duration of the show, the buying crowds came early, partially to avoid the heat of the afternoon. There were plenty of bags and going by  and I had a lot of purchases and  positive comments from patrons that they had not seen my work before. The heat of the afternoon took its toll on the crowds as it definitely thinned out mid-afternoon. I did have a burst of activity in the last hour to complete a $2.5K day. The judging came through and I did have a piece selected for judging. At the close of the show on Friday I carried my piece over to the Catholic Church a block away. I saw dozens of other artists carrying/dollying their pieces as well. I was informed that we had to pick up our pieces Saturday between 11:30am - 12:30pm. No worries though, I secured a booth sitter so I could make the run over to the church. 

Saturday promised another beautiful day and once again, the crowds came early and the free SunRail was dropping off customers by the trainload at the festival doorstep. I did see a bit of a different demographic with more families and the kettle corn crowd coming in. Sales did occur once again early in the day and once again late in the afternoon. Another 2K day for me. The music on the lawn in the North Central Park went on for most of the day. It wasn't too loud for me, although I did have a several booth buffer between me and the stage. At the close of the day I walked two blocks over to the Farmer's Market for the artists dinner/awards. I didn't win an award but the dinner was FANTASTIC. Catered by a local company and plenty of libations for us. Congrats to the winners! 

Sunday was basically a repeat of Saturday. Sales early before the heat set in, lots of people although I did have a four hour gap in the middle of the day without a sale. Then, once again, on cue...a flurry of sales in the last hour. That seemed to be the M.O. of the crowd. It was another 2K day for me.  One of the show volunteers came by late in the day and gave load out procedures. Police would open up the street about 6pm for load out. I had my egress already planned out though. Break down, dolly out across the tracks straight to the parking area. I was loaded up and on the road by 5:45, headed to Hollywood Florida for 5 days at the beach! 

Overall, I could not have asked for a better show. Winter Park lived up to the hype for me! Sales! Sales! Sales! A great volunteer staff and a beautiful city! I'm already looking forward to applying to the 2016 show and fingers crossed, that I get juried in! 


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  • Friday was certainly a determined buying crowd. Those looking to get first dibs and to spend their Patrons Bucks that they had committed to purchasing art. Saturday and Sunday was definitely more of a family affair. Folks out and about in groups looking to spend time with their loved ones on a fantastic spring weekend, especially with the SunRail running for free both days. 

  • Way to go, Matt! So pleased for you. Solid report. Hope you get in again next year.

    Sounds like all three days had similar sales. Did you notice a difference in the crowd from one day to the next?

    To my mind, just like on Saturdays in the fall because of college football, this show does have some slow time because of March Madness, which draws people away from the show, in the heart of the day. 

    We used to hang out at Hollywood Beach between shows too. Laid back and great food.

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