Upcoming Winter Garden Events

Check out what's happening 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

Dream Finders Homes Hippity Hop 5K

 Sat, 04 Apr at 08:00 am Winter Garden/Windermere

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

Dream Finders Home Mother's Day 5K

 Sun, 10 May at 08:00 am Orlando Health Horizon West Hospital

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

Sip, Snack, Shop and Socialize

Fri, 06 Feb at 06:00 pm 50 East Joiner Street, Winter Garden, FL

The Chuck Wagon Gang In Concert

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

N.O.W. Matters More Celebrity Golf

 Mon, 20 Apr at 08:00 am Orange County National Golf Center and Lodge USD 429 to 1,282

Healthy YOU Day!

 Thu, 12 Feb at 05:00 pm 100 Windermere Rd, Winter Garden, FL 34787

Pours at the Preserve

 Sat, 07 Mar at 05:30 pm Oakland Nature Preserve

Amigas & Margaritas | The Whole Enchilada Winter Garden

 Wed, 11 Feb at 06:00 pm The Whole Enchilada Fresh Mexican Grill & Bar Free

Meditative Hike & Yoga at the Lake

 Sun, 08 Mar at 09:00 am Oakland Nature Preserve

5th Annual Cornhole Tournament

 Sat, 11 Apr at 09:00 am Cornerstone Community Church

Bethune Cookman Inspirational Gospel Choir

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

Valentine’s Partner Yoga

 Sun, 15 Feb at 10:00 am Home State Brewing Co. USD 10

Valentine’s Cherry Paint Pop Up

 Sat, 28 Feb at 11:00 am Home State Brewing Co. USD 19

🍫✨ Ladies Chocolate Crawl Winter Garden

 Sun, 08 Feb at 02:00 pm Way Chocolate & Coffee

Parent's Night Out!

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

Meditative Hike & Yoga at the Lake

 Sun, 08 Feb at 09:00 am Oakland Nature Preserve

Meditative Hike & Yoga at the Lake

 Sun, 22 Mar at 09:00 am Oakland Nature Preserve

Open Gym!

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

FREE Saturday Camp

 Sat, 07 Feb at 07:15 am 15512 West Colonial Dr, Winter Garden, FL

Open Gym!

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

SOLFORGE: Tournament & Training

 Fri, 13 Feb at 02:00 pm Crossroads Swords - West Orlando HEMA

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

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

Journey into the Uplands Guided Hike

Sat, 21 Feb at 09:00 am Oakland Nature Preserve

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

 Thu, 05 Mar at 06:30 pm 15304 Tilden Rd, Winter Garden, FL 34787-5317, United States

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

Spanish-Style Tapas - Winter Garden

 Sun, 26 Apr at 05:15 pm The Ancient Olive Gourmet of Winter Garden USD 82

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

FREE Saturday Camp

 Sat, 07 Mar at 07:15 am 15512 West Colonial Dr, Winter Garden, FL

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

 Fri, 13 Feb at 06:00 pm UNO Pizzeria & Grill USD 115

Sock Hop

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

Journey into the Uplands Guided Hike

Sat, 28 Mar at 09:00 am Oakland Nature Preserve

Love at First Tour: Exclusive VIP Realtor Event with Dream Finders Homes

 Fri, 13 Feb at 11:00 am Avalon Woods by Dream Finders Homes Free

Foundations Year 1 ~ IIOSHEM Practitioner Training

Thu, 26 Feb at 09:00 am Divine Energy Healing

IIOSHEM 2026 Foundations Year 1 Class 1 Enrollment

 Thu, 26 Feb at 09:00 am Divine Energy Healing

Downtown Winter Garden Walking Tour

 Sat, 07 Feb at 08:30 am 101 S Boyd St, Winter Garden, FL, United States, Florida 34787

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

5th Annual Benefit Motorcycle Ride

 Sat, 21 Feb at 09:00 am 700 9th St, Winter Garden, FL

OCPN City Gathering | March 2026

 Wed, 11 Mar at 12:00 pm Mosaic Church Free

Fencing Referee Clinic - Division Sponsored

 Sat, 21 Feb at 10:00 am Winter Garden Fencing Academy

Learn Lightroom and Photoshop

 Sat, 07 Feb at 09:00 am Plant St. Market

TLE Windermere Spirit Night at Blaze Pizza

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

Rib Cook-Off

 Sat, 28 Feb at 07:00 am 700 9th St, Winter Garden, FL

Knife Skills 101 (Winter Garden)

 Sun, 22 Feb at 05:15 pm The Ancient Olive Gourmet of Winter Garden USD 66

Everyday Cuban Food - Winter Garden

 Sun, 29 Mar at 05:15 pm The Ancient Olive Gourmet of Winter Garden USD 82

Central Florida Watercolor Workshop!

Mon, 02 Mar at 09:00 am Winter Garden Art Association

Member Meeting ~ Monthly

 Tue, 17 Feb at 06:00 pm The Blake at Hamlin

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

Giving On the Green

 Mon, 30 Mar at 12:00 pm West Orange Country Club

Native Heart Drum Journey

Sat, 07 Mar at 11:45 am Oakland Nature Preserve

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

Mere Christians

 Fri, 24 Apr at 09:00 am Church of the Messiah Episcopal USD 98

UCP West Orange Spring Community Market & Art Show

 Sat, 18 Apr at 10:00 am 1441 Winter Garden Vineland Road, Winter Garden, FL, United States, Florida 34787

CFWS March General Meeting

Sun, 01 Mar at 01:30 pm Winter Garden Art Association

Grace Pointe Church-Winter Garden ,Florida

Sun, 08 Feb at 11:00 am GracePointe Winter Garden

Shamrock Scavenger Hunt

 Fri, 13 Mar at 03:00 pm 5795 Citrus Village Blvd, Winter Garden, FL

The Learning Experience Windermere Spirit Night at Tijuana Flats Hamlin

 Wed, 18 Feb at 04:00 pm Tijuana Flats Free

Ash Wednesday

 Wed, 18 Feb at 07:00 pm 125 N Lakeview Ave, Winter Garden, FL, United States, Florida 34787

Two Day Business and Billing Mastermind Weekend - Orlando, FL

 Fri, 15 May at 08:30 am Homewood Suites by Hilton Orlando at FLAMINGO CROSSINGS Town Center USD 394 to 507

WG Elks 5th Annual Benefit Ride

 Sat, 21 Feb at 09:00 am Winter Garden Elks Lodge 2165

National Pizza Day | AJ's Pizza Joint

 Mon, 09 Feb at 11:00 am AJ's Pizza Joint Free

Nature Walk + Social at the Oakland Nature Preserve

 Thu, 26 Mar at 06:00 pm Oakland Nature Preserve

Open House- Mardi Gras in Winter Garden

 Fri, 13 Feb at 10:00 am AdventHealth Well 65+ Winter Garden Free

VFW POST 4305 Saturday Bingo

 Sat, 07 Feb at 12:00 pm 1170 E Plant St, Winter Garden, FL

FEBRUARY 2026 IronMen of God Coffee

 Fri, 27 Feb at 07:00 am 146 W Plant St, Winter Garden, FL, United States, Florida 34787

OCPN City Gathering | April 2026

 Wed, 08 Apr at 12:00 pm Mosaic Church Free

February Galentine's Mahjong Open Play at LiveTrends Boutique

 Tue, 10 Feb at 06:00 pm LiveTrends Boutique USD 19

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

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

Avalon Woods By Dream Finders Homes Grand Opening

 Sat, 14 Feb at 12:00 pm Avalon Woods by Dream Finders Homes Free

Wine & Edible Designs

 Wed, 18 Feb at 05:00 pm 5795 Citrus Village Blvd, Winter Garden, FL

Common Read - Session IV: Collage and Connection

 Wed, 11 Mar at 11:30 am Healthy West Orange Free

Pullman: America’s Hotel on Wheels

 Sat, 14 Feb at 01:30 pm 101 S Boyd St, Winter Garden, FL, United States, Florida 34787

Further Together Orlando

 Wed, 18 Feb at 10:00 am 9230 Miley Dr USD 47

MomCo Winter Garden Meetup #11 SURPRISE topic (Downtown)

 Thu, 02 Apr at 06:30 pm 125 E Plant St, Winter Garden, FL 34787-3128, United States

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

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

Homeschool class-cold blooded animals

Mon, 23 Feb at 10:00 am Oakland Nature Preserve

Preserving Autonomy: Advance Care Planning & Related Legal Matters

 Thu, 26 Feb at 01:00 pm AdventHealth Well 65+ Winter Garden Free

Copy of Deep Dish Pizza Cooking Class - Winter Garden, FL

 Sat, 10 Jan at 12:00 pm UNO Pizzeria & Grill USD 69

5th Annual Central Florida Chili Cookoff

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

Game Days At AJ's Pizza Joint

 Thu, 15 Jan at 07:00 pm AJ's Pizza Joint Free

"THE SHIFT IS NOW!!"

 Sat, 28 Mar at 12:00 pm 1114 E Plant St Free

IIOSHEM YR 2 - Class 1 - Enrollment

Thu, 30 Apr at 09:00 am Divine Energy Healing