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Pride in Winter Garden, FL
Girls in Wonderland is usually first weekend of June (Gay Days weekend); organizers say June 2027 is coming; the 2027 date isn't announced yet. We've mapped 1 Pride event in Winter Garden and 12 more nearby (7 festivals, 5 Pride nights, 1 drag show / brunch). 3 are free. Tap any event for dates, places and directions.
Updated Nov 13, 2026. Events without a confirmed date show the pattern from past years.
Near Winter Garden (within 25 miles)
Tap + Plan on a few events to map them together and send the plan to your phone (how it works). Missing a Winter Garden event? Add it free.
Pride in Winter Garden: common questions
When is Pride in Winter Garden?
GayDays Orlando is Jun 3 – 7, 2027 at Official GayDays host hotel (2026: Holiday Inn & Suites Orlando SW, Celebration area). One Magical Weekend (Jun 3 – 7, 2027) is also on the calendar.
Are there family-friendly Pride events near Winter Garden?
Yes. All-ages options include PrideFest Kissimmee, Come Out With Pride Orlando Festival & Parade, Red Shirt Pride Day at Magic Kingdom and Pride in Our City (Orlando Pride NWSL match). Daytime parades and festivals are generally fine for kids; drag shows and late-night parties are usually 18+ or 21+.
Where can I find a drag brunch or drag show in Winter Garden?
Peacocks & Divas Drag Brunch (Winter Park Pride Project) (12 PM - 3 PM (2026)). Drag brunches usually need reservations, especially in June.
Are Pride events in Winter Garden free?
3 of the 13 events listed near Winter Garden are free, including PrideFest Kissimmee, Come Out With Pride Orlando Festival & Parade and Love & Liberation: Juneteenth Pride Celebration. Some festivals charge a gate fee or sell VIP passes, and drag brunches and Pride nights at venues are ticketed.
Organizing Pride in Winter Garden?
Add your parade, festival, march, drag brunch, youth Pride or Pride night free. Post your date as soon as it's set and we'll show it here, on the Pride calendar and on the map.
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