All Upcoming events

• Sat, 21 Feb, 2026 - 11:00 AM

  Winter Garden Music Festival

  300 W. Plant Street, Winter Garden, FL, United States, Florida 34787

  1608+ Interested
• Thu, 04 Jun, 2026 - 01:00 PM

  GIW aka Girls in Wonderland- Orlando 2026 - Tickets Only

  SPRINGHILL SUITES and TOWNEPLACE SUITES

  USD 24
• Thu, 04 Jun, 2026 - 10:00 AM

  GIW Orlando / Passes June 4–8, 2026

  SPRINGHILL SUITES & TOWNEPLACE SUITES

  USD 29
• Sat, 07 Mar, 2026 - 11:00 AM

  Horizon West Fest - 2026

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

  1419+ Interested
• Fri, 28 Aug, 2026 - 05:30 PM

  V Encontro da Fé Reformada '26

  Mosaic Church | Winter Garden

  USD 15
• Sun, 01 Mar, 2026 - 09:00 AM

  Homegrown BARK-ET DAY!

  16016 New Independence Pkwy, Winter Garden, FL, United States, Florida 34787

  175+ Interested
• Sun, 15 Mar, 2026 - 08:00 AM

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

  Home State Brewing Co.

  300+ Interested
• Sat, 04 Apr, 2026 - 08:00 AM

  Dream Finders Homes Hippity Hop 5K

  Winter Garden/Windermere

  140+ Interested
• Sat, 28 Mar, 2026 - 07:00 PM

  Evening at the Pops

  29 Garden Ave, Winter Garden, FL, United States, Florida 34787

  80+ Interested
• Sun, 10 May, 2026 - 08:00 AM

  Dream Finders Home Mother's Day 5K

  Orlando Health Horizon West Hospital

  88+ Interested
• Fri, 06 Mar, 2026 - 06:30 PM

  March Of The Muses

  Winter Garden Pavilion

  5+ Interested
• Mon, 20 Apr, 2026 - 08:00 AM

  N.O.W. Matters More Celebrity Golf

  Orange County National Golf Center and Lodge

  USD 429
• Sat, 21 Feb, 2026 - 10:00 AM

  Fencing Referee Clinic - Division Sponsored

  Winter Garden Fencing Academy

  5+ Interested
• Sat, 21 Feb, 2026 - 12:00 PM

  VFW POST 4305 Saturday Bingo

  1170 E Plant St, Winter Garden, FL
• Sat, 11 Apr, 2026 - 09:00 AM

  5th Annual Cornhole Tournament

  Cornerstone Community Church

  18+ Interested
• Sat, 28 Feb, 2026 - 11:00 AM

  Valentine’s Cherry Paint Pop Up

  Home State Brewing Co.

  USD 19
• Sat, 07 Mar, 2026 - 05:30 PM

  Pours at the Preserve

  Oakland Nature Preserve

  104+ Interested
• Fri, 27 Mar, 2026 - 06:30 PM

  Parent's Night Out!

  13175 West Colonial Drive, Winter Garden, FL, United States, Florida 34787

  7+ Interested
• Thu, 26 Feb, 2026 - 06:30 PM

  MomCo Winter Garden Meetup #9 Enjoy the Joy! (Downtown)

  125 E Plant St, Winter Garden, FL 34787-3128, United States

  15+ Interested
• Sun, 08 Mar, 2026 - 09:00 AM

  Meditative Hike & Yoga at the Lake

  Oakland Nature Preserve

  8+ Interested
• Fri, 20 Feb, 2026 - 07:00 PM

  KARAOKE NIGHT 🎤🎶 @ VFW POST 4305

  1170 E Plant St, Winter Garden, FL
• Thu, 05 Mar, 2026 - 06:30 PM

  MomCo Winter Garden meetup #10 Audacious Faith (Horizon West)

  15304 Tilden Rd, Winter Garden, FL 34787-5317, United States

  6+ Interested
• Sun, 26 Apr, 2026 - 05:15 PM

  Spanish-Style Tapas - Winter Garden

  The Ancient Olive Gourmet of Winter Garden

  USD 82
• Sat, 21 Feb, 2026 - 09:00 AM

  Journey into the Uplands Guided Hike

  Oakland Nature Preserve

  58+ Interested
• Thu, 26 Feb, 2026 - 09:00 AM

  IIOSHEM 2026 Foundations Year 1 Class 1 Enrollment

  Divine Energy Healing
• Sat, 07 Mar, 2026 - 07:15 AM

  FREE Saturday Camp

  15512 West Colonial Dr, Winter Garden, FL
• Sun, 22 Feb, 2026 - 05:15 PM

  Knife Skills 101 (Winter Garden)

  The Ancient Olive Gourmet of Winter Garden

  USD 66
• Tue, 17 Feb, 2026 - 06:00 PM

  Member Meeting ~ Monthly

  The Blake at Hamlin

  6+ Interested
• Sat, 28 Feb, 2026 - 01:00 PM

  Boozy Book Fair at Homestate Brewing with Authors, Trivia, and Crafts

  Home State Brewing Co.

  Free
• Sun, 12 Apr, 2026 - 05:15 PM

  Dessert Trio for Any Occasion - Winter Garden

  The Ancient Olive Gourmet of Winter Garden

  USD 82
• Sat, 21 Feb, 2026 - 09:00 AM

  5th Annual Benefit Motorcycle Ride

  700 9th St, Winter Garden, FL

  79+ Interested
• Sat, 07 Mar, 2026 - 08:00 AM

  Free Homebuyer Education Seminar (8 hours)

  Maxey Community Center

  Free
• Sat, 28 Feb, 2026 - 06:00 PM

  Love at the Lake - Valentine's Gala Dinner

  Stoneybrook West Golf Club

  USD 109
• Sat, 28 Mar, 2026 - 03:00 PM

  3rd Annual Hamlin Craft Beer Festival - Presented by Legacy Events for Education

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

  506+ Interested
• Fri, 06 Mar, 2026 - 06:30 PM

  Open Gym!

  13175 West Colonial Drive, Winter Garden, FL, United States, Florida 34787

  8+ Interested
• Mon, 09 Mar, 2026 - 05:00 PM

  TLE Windermere Spirit Night at Blaze Pizza

  Blaze Pizza

  Free
• Sun, 29 Mar, 2026 - 05:15 PM

  Everyday Cuban Food - Winter Garden

  The Ancient Olive Gourmet of Winter Garden

  USD 82
• Mon, 02 Mar, 2026 - 09:00 AM

  Central Florida Watercolor Workshop!

  Winter Garden Art Association
• Fri, 27 Mar, 2026 - 09:00 AM

  Film Making Day at the Florida Film & STEM Academy

  Florida Film & STEM Academy

  66+ Interested
• Tue, 17 Feb, 2026 - 02:00 PM

  Panda Express Little Fortune Festival

  13348 Hartzog Rd

  Free
• Sat, 28 Feb, 2026 - 07:00 AM

  Rib Cook-Off

  700 9th St, Winter Garden, FL

  31+ Interested
• Sat, 21 Mar, 2026 - 09:30 AM

  Retiro da Quaresma com Padre Fábio Marinho - Resurrection Catholic Church

  1211 Winter Garden Vineland Rd

  USD 13
• Sat, 07 Mar, 2026 - 11:45 AM

  Native Heart Drum Journey

  Oakland Nature Preserve

  33+ Interested
• Sat, 18 Apr, 2026 - 10:00 AM

  UCP West Orange Spring Community Market & Art Show

  1441 Winter Garden Vineland Road, Winter Garden, FL, United States, Florida 34787

  12+ Interested
• Mon, 30 Mar, 2026 - 12:00 PM

  Giving On the Green

  West Orange Country Club

  43+ Interested