Entertainment events in Winter Garden

• Thu, 04 Jun, 2026 - 10:00 AM

  GIW Orlando / Passes June 4–8, 2026

  SPRINGHILL SUITES & TOWNEPLACE SUITES

  USD 29
• Sun, 15 Mar, 2026 - 08:00 AM

  Lucky Charm 5K & 10K at Home State Brewing Company

  Home State Brewing Co.

  233+ Interested
• Fri, 16 Jan, 2026 - 07:00 PM

  KARAOKE NIGHT 🎤🎶 @ VFW POST 4305

  1170 E Plant St, Winter Garden, FL
• Mon, 19 Jan, 2026 - 07:00 PM

  👑❤️POST 4305 QUEEN OF HEARTS❤️👑

  1170 E Plant St, Winter Garden, FL
• Fri, 06 Feb, 2026 - 07:00 PM

  The Chuck Wagon Gang in Winter Garden

  Temple Free Will Baptist Church
• Fri, 23 Jan, 2026 - 06:00 PM

  Branded Roots & Co. Anniversary Party!

  636 South Dillard Street, Winter Garden, FL, United States, Florida 34787

  67+ Interested
• Fri, 27 Mar, 2026 - 09:00 AM

  Film Making Day at the Florida Film & STEM Academy

  Florida Film & STEM Academy

  59+ Interested
• Mon, 19 Jan, 2026 - 06:30 PM

  Is Your Daughter Struggling with Confidence or Friendships? This 10-Week Group Changes Everything.

  Hi-Lite Youth Programs

  7+ Interested
• Fri, 30 Jan, 2026 - 09:00 AM

  Sell your camera gear (free event-no ticket needed) at The Lens Pal

  The LensPal

  Free
• Sat, 07 Feb, 2026 - 12:00 PM

  5th Annual Central Florida Chili Cookoff

  14111 Shoreside Way, Winter Garden, FL 34787-5611, United States

  152+ Interested