- December 18, 2025
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Spring ushers in art festival associated events
The signs of the season are around every corner in Winter Park. The Great Duck Derby has come and gone at Mead Botanical Gardens, the azaleas are in bloom, and preparations are underway for the true mark of spring in Winter Park: the Winter Park Sidewalk Art Festival. The festival returns March 15 – 17.
Kick off art festival festivities on Thursday, March 14, with some early-bird shopping at the Park Avenue area spring sidewalk sale. Save on gifts, fashions and more! The sale continues all weekend, but the best selection is on Thursday before the crowds arrive.
Celebrate the art of fine wine with the Winter Park Chamber of Commerce and Hannibal Square Merchants Association at the Hannibal Square Wine Tasting. This street party celebration features more than 40 wine and beer samples, plus tasty appetizers from local restaurants including Dexter’s, Armando’s, mi Tomatina and Fresh Cafe. Mark your calendar for March 14 and visit winterpark.org to reserve your ticket.
The fun begins on Friday at 9 a.m. with 225 nationally and internationally renowned artists displaying their talent in Central Park at the Winter Park Sidewalk Art Festival. This is also when people start spreading their blankets on the grass near the Central Park stage for the Friday night concert. Check out the entertainment schedule and other festival details at wpsaf.org
Car parking for a cause
Parking will be at a premium for the weekend, and while many local Scout troops, sports teams and school groups will organize parking lots throughout downtown, please consider supporting Leadership Winter Park when searching for a parking space. Leadership Winter Park provides leadership development opportunities for youth, adults and seniors in our community. Monies raised during the festival will support scholarships for these programs. Members of the current class as well as alumni will be manning parking lots all weekend at the Winter Park Welcome Center on Lyman Avenue. On Saturday and Sunday, the group also will be raising funds at Florida Community Bank and Cooper, Simms, Nelson & Mosley Insurance at the corner of New York and Canton avenues.
Small business education series kicks off
If the art festival isn’t your thing, you’ll be happy to know that non-art festival related business is going on in Winter Park. Small business owners will be happy to hear the Winter Park Chamber is partnering with the Small Business Resource Network to launch a monthly seminar series to provide insight and training on topics to help grow and sustain businesses in our community. Chamber members can look forward to a free program each month on a different topic; there is a small fee for non-members to participate.
The first in this new series will be Friday, March 22, at 8 a.m. at the Winter Park Welcome Center. The program will feature Kyle Taylor from Thriving Interactive who will discuss local Internet search marketing. For more information, visit winterpark.org
Erika Spence is the senior director of marketing and communications at the Winter Park Chamber of Commerce.