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

  1611+ 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
• Sat, 21 Feb, 2026 - 05:00 PM

  Tom Jackson Band at Winter Garden Music Festival

  427 W. Plant Street Main Street Stage, 1 N. Main Street
• 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, 21 Feb, 2026 - 08:00 PM

  Julie Black & Her Band at Winter Garden Music Festival

  Winter Garden City hall
• Thu, 12 Mar, 2026 - 07:00 PM

  Celtic Angels Ireland 🍀🇮🇪

  Garden Theatre
• Sat, 28 Mar, 2026 - 07:00 PM

  Evening at the Pops

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

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

  March Of The Muses

  Winter Garden Pavilion

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

  Dream Finders Home Mother's Day 5K

  Orlando Health Horizon West Hospital

  88+ 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, 28 Feb, 2026 - 08:00 AM

  PopStroke Hamlin X CARVE Pilates PopUp Event

  PopStroke Hamlin

  Free
• Sat, 21 Feb, 2026 - 10:00 AM

  Fencing Referee Clinic - Division Sponsored

  Winter Garden Fencing Academy

  5+ Interested
• Sat, 21 Feb, 2026 - 10:00 AM

  Kundalini Flow Retreat - A Journey Through the Chkaras

  342 E. Plant Street, Winter Garden, FL
• Sat, 11 Apr, 2026 - 09:00 AM

  5th Annual Cornhole Tournament

  Cornerstone Community Church

  18+ Interested
• Sat, 07 Mar, 2026 - 05:30 PM

  Pours at the Preserve

  Oakland Nature Preserve

  104+ Interested
• Sat, 21 Feb, 2026 - 10:00 AM

  Petsmart Adoption Day 10:00AM-noon

  PetSmart (Winter Garden, FL)
• Fri, 27 Mar, 2026 - 06:30 PM

  Parent's Night Out!

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

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

  Valentine’s Cherry Paint Pop Up

  Home State Brewing Co.

  USD 19
• Sat, 21 Mar, 2026 - 08:00 AM

  FREE YOGA FLOW AT POPSTROKE HAMLIN

  PopStroke

  Free
• Sat, 21 Feb, 2026 - 12:00 PM

  Shot of Poison at Winter Garden Music Festival

  320 Windford Ct, Winter Garden, FL 34787-6061, United States
• 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
• Fri, 27 Feb, 2026 - 11:00 AM

  MTG TMNT Prerelease

  13750 W Colonial Dr Ste 290, Winter Garden, FL, United States, Florida 34787
• Tue, 24 Feb, 2026 - 01:30 PM

  Girlfriends Twenty-Thirty | Pottery Painting Social (Winter Garden)

  Color Me Mine (Winter Garden, FL)
• Sun, 08 Mar, 2026 - 12:30 PM

  Self Care Sunday-2 Mile Walk

  West Orange Trail

  USD 7
• Sat, 28 Feb, 2026 - 09:00 AM

  Paddles for the Past: Inaugural Pickleball Tournament @ Roper YMCA

  Roper YMCA
• 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, 22 Feb, 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
• Wed, 25 Feb, 2026 - 05:00 PM

  Seuss Party Meet & Greet

  3167 Daniels Rd, Winter Garden, FL 34787
• 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
• Tue, 24 Feb, 2026 - 05:00 PM

  Crazy Socks Craft Night

  3167 Daniels Rd, Winter Garden, FL 34787
• Fri, 06 Mar, 2026 - 09:00 AM

  Screening for Free Dental Clinic

  1136 East Plant St., Winter Garden, FL, United States, Florida 34787
• Sat, 07 Mar, 2026 - 07:15 AM

  FREE Saturday Camp

  15512 West Colonial Dr, Winter Garden, FL
• Thu, 26 Feb, 2026 - 09:00 AM

  IIOSHEM 2026 Foundations Year 1 Class 1 Enrollment

  Divine Energy Healing
• Sat, 07 Mar, 2026 - 12:00 PM

  Dragon Fest 2026

  311 N. Dillard, Winter Garden, FL, United States, Florida 34787
• Sun, 15 Mar, 2026 - 09:00 AM

  Homegrown in Horizon West Market

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