Entertainment events in Winter Garden

Check out happening entertainment events all around Winter Garden, FL

Winter Garden Music Festival

 Sat, 21 Feb at 11:00 am 300 W. Plant Street, Winter Garden, FL, United States, Florida 34787

GIW Orlando / Passes June 4–8, 2026

 Thu, 04 Jun at 10:00 am SPRINGHILL SUITES & TOWNEPLACE SUITES USD 29 to 333

Horizon West Fest - 2026

 Sat, 07 Mar at 11:00 am 14111 Shoreside Way, Winter Garden, FL 34787-5611, United States

Homegrown BARK-ET DAY!

Sun, 01 Mar at 09:00 am 16016 New Independence Pkwy, Winter Garden, FL, United States, Florida 34787

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

 Sun, 15 Mar at 08:00 am Home State Brewing Co.

Hear ye, hear ye! Home State turns IV!

 Sat, 07 Feb at 04:00 pm 16016 New Independence Pkwy #100, Winter Garden, FL

Homegrown in Horizon West Market & Children’s Entrepreneur Market

 Sun, 15 Feb at 09:00 am 16016 New Independence Pkwy, Winter Garden, FL

The Chuck Wagon Gang in Winter Garden

 Fri, 06 Feb at 07:00 pm Temple Free Will Baptist Church

Evening at the Pops

 Sat, 28 Mar at 07:00 pm 29 Garden Ave, Winter Garden, FL, United States, Florida 34787

March Of The Muses

 Fri, 06 Mar at 06:30 pm Winter Garden Pavilion

Super Sunday Watch Party

 Sun, 08 Feb at 06:00 pm 15501 Towne Common Boulevard, Winter Garden, FL, United States, Florida 34787

The Chuck Wagon Gang In Concert

 Fri, 06 Feb at 07:00 pm 1208 E Story Rd, Winter Garden, FL, United States, Florida 34787

Bethune Cookman Inspirational Gospel Choir

 Sun, 08 Feb at 09:00 am 125 N Lakeview Ave, Winter Garden, FL, United States, Florida 34787

Parent's Night Out!

 Fri, 27 Mar at 06:30 pm 13175 West Colonial Drive, Winter Garden, FL, United States, Florida 34787

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

Thu, 26 Feb at 06:30 pm 125 E Plant St, Winter Garden, FL 34787-3128, United States

Film Making Day at the Florida Film & STEM Academy

 Fri, 27 Mar at 09:00 am Florida Film & STEM Academy

Valentine's Day Parent's Night Out!

 Fri, 13 Feb at 06:30 pm 13175 West Colonial Drive, Winter Garden, FL, United States, Florida 34787

Pregame For The BIG GAME | The Whole Enchilada Winter Garden

 Sun, 08 Feb at 10:00 am The Whole Enchilada Fresh Mexican Grill & Bar Free

UNO Winter Garden - Big Game All-U-Can-Eat Pizza & Wings Watch Party at UNO

 Sun, 08 Feb at 05:00 pm UNO Pizzeria & Grill USD 36

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

 Sat, 28 Mar at 03:00 pm 14111 Shoreside Way, Winter Garden, FL 34787-5611, United States

Sock Hop

 Sat, 07 Feb at 05:00 pm Resurrection Catholic Church

Love at the Lake - Valentine's Gala Dinner

 Sat, 28 Feb at 06:00 pm Stoneybrook West Golf Club USD 109

Dessert Trio for Any Occasion - Winter Garden

 Sun, 12 Apr at 05:15 pm The Ancient Olive Gourmet of Winter Garden USD 82

KARAOKE NIGHT 🎤🎶 @ VFW POST 4305

 Fri, 06 Feb at 07:00 pm 1170 E Plant St, Winter Garden, FL

TLE Windermere Spirit Night at Blaze Pizza

 Mon, 09 Mar at 05:00 pm Blaze Pizza Free

Game On Video Game Design and Coding

Mon, 16 Feb at 09:00 am 1261 Winter Garden Vineland Rd suite 250, Winter Garden, FL 34787, USA

SUPERBOWL LX @ VFW 4305 🏈

 Sun, 08 Feb at 05:00 pm 1170 E Plant St, Winter Garden, FL

BOOSTER BOS$ & SCF 2026

 Sat, 07 Feb at 08:00 am 17800 Bali Blvd

The Big Game Watch Party | AJ's Pizza Joint

 Sun, 08 Feb at 11:00 am AJ's Pizza Joint Free

City Lights: Music • Arts • Faith

 Fri, 27 Feb at 09:45 pm West Orange Dream Center USD 0 to 5

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

 Fri, 05 Jun at 09:00 am The LensPal Free

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

 Thu, 30 Oct at 08:00 pm Winter Garden Free

5th Annual Central Florida Chili Cookoff

 Sat, 07 Feb at 12:00 pm 14111 Shoreside Way, Winter Garden, FL 34787-5611, United States

Wizard of Oz Experience - Winter Garden

 Fri, 05 Dec at 08:00 am Wizard of Oz Experience - Winter Garden USD 24 to 64