Upcoming Food & Drinks Events

Sip, Snack, Shop and Socialize

50 East Joiner Street, Winter Garden, FL 6 Feb 2026
FOOD-DRINKS

Seasonal Soups (Winter Garden)

 The Ancient Olive Gourmet of Winter Garden 1 Feb 2026
WORKSHOPS USD 82

Pours at the Preserve

 Oakland Nature Preserve 7 Mar 2026

View More Food & Drinks Events

Upcoming Valentine's Day Events

SOLFORGE: Tournament & Training

 Crossroads Swords - West Orlando HEMA 13 Feb 2026
WORKSHOPS

UNO Winter Garden- Valentine's Day Deep Dish Pizza Cooking Classes & Dinner

 UNO Pizzeria & Grill 13 Feb 2026
COOKING USD 115

Valentine's Day Parent's Night Out!

 13175 West Colonial Drive, Winter Garden, FL, United States, Florida 34787 13 Feb 2026
SPORTS

View More Valentine's Day Events

Upcoming Festivals Events

Horizon West Fest - 2026

 14111 Shoreside Way, Winter Garden, FL 34787-5611, United States 7 Mar 2026
FESTIVALS

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

 14111 Shoreside Way, Winter Garden, FL 34787-5611, United States 28 Mar 2026
BEER-FESTIVALS

5th Annual Central Florida Chili Cookoff

 14111 Shoreside Way, Winter Garden, FL 34787-5611, United States 7 Feb 2026
KIDS

View More Festivals Events

Upcoming Comedy Events

GIW Orlando / Passes June 4–8, 2026

 SPRINGHILL SUITES & TOWNEPLACE SUITES 4 Jun 2026
PARTIES USD 29 TO 333

90's Sitcoms Trivia

16016 New Independence Pkwy #100, Winter Garden, FL, United States, Florida 34787 28 Jan 2026

Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!

 Winter Garden 30 Oct 2025
ART FREE

View More Comedy Events

Trending Events in Winter Garden

Open House- Mardi Gras in Winter Garden

 AdventHealth Well 65+ Winter Garden 13 Feb 2026
MARDI-GRAS FREE

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

 Home State Brewing Co. 15 Mar 2026
SPORTS

Shamrock Scavenger Hunt

 5795 Citrus Village Blvd, Winter Garden, FL 13 Mar 2026
TRIPS-ADVENTURES

Hear ye, hear ye! Home State turns IV!

 16016 New Independence Pkwy #100, Winter Garden, FL 7 Feb 2026
MUSIC

The Chuck Wagon Gang in Winter Garden

 Temple Free Will Baptist Church 6 Feb 2026
CONCERTS

SUPERBOWL LX @ VFW 4305 🏈

 1170 E Plant St, Winter Garden, FL 8 Feb 2026
SPORTS

Dream Finders Homes Hippity Hop 5K

 Winter Garden/Windermere 4 Apr 2026
SPORTS

Dream Finders Home Mother's Day 5K

 Orlando Health Horizon West Hospital 10 May 2026
SPORTS

Parent's Night Out!

 13175 West Colonial Drive, Winter Garden, FL, United States, Florida 34787 23 Jan 2026
SPORTS

The Chuck Wagon Gang In Concert

 1208 E Story Rd, Winter Garden, FL, United States, Florida 34787 6 Feb 2026
CONCERTS

N.O.W. Matters More Celebrity Golf

 Orange County National Golf Center and Lodge 20 Apr 2026
SPORTS USD 429 TO 1,282

Meditative Hike & Yoga at the Lake

 Oakland Nature Preserve 25 Jan 2026
HEALTH-WELLNESS

Healthy YOU Day!

 100 Windermere Rd, Winter Garden, FL 34787 12 Feb 2026
HEALTH-WELLNESS

Mahjong For Two at LiveTrends Boutique

 LiveTrends Boutique 28 Jan 2026
WORKSHOPS USD 230

Babes, Booze, & Business West Orange County Inaugural 2026 Meet Up 2

 Trophies Unlimited 27 Jan 2026
MEETUPS

More things to do in Winter Garden

Food & Drinks
Valentine's Day
Festivals
Super Bowl
Live Music
Comedy
St. Patrick's Day
Mardi Gras
Easter
Martin Luther King Day
Presidents Day
Music Festivals
Pop-Ups