Upcoming Winter Garden Events

Check out what's happening all around Winter Garden, FL

Flavor Fest: A Taste of Horizon West!

Sat, 08 Nov at 05:00 pm 14111 Shoreside Way Winter Garden, FL, United States, Florida 34787

2nd Annual effNETS Golf Tournament

 Fri, 21 Nov at 08:30 am Stoneybrook West Golf Club

Church Revival

 Fri, 07 Nov at 07:00 pm 1320 S. 9th Street, Winter Garden, FL, United States, Florida 34787

TRAVELING SKETCHBOOKS Lecture - The World through Urban Sketchers' eyes!

 Sat, 01 Nov at 10:00 am SOBO Art Gallery - Winter Garden Art Association Free

America's Fleetwood Mac Experience - Be an usher!

 Fri, 14 Nov at 05:00 pm Horizon High School Performing Arts Center Free

Annual Fall Festival

 Sat, 01 Nov at 03:00 pm 15501 Towne Common Boulevard, Winter Garden, FL

Movie In The Park 2025 - Independence Park

 Fri, 07 Nov at 06:00 pm Independence Park Free

Challenge 22 Ruck Walk 2025

 Sat, 15 Nov at 09:00 am Winter Garden Downtown Historic District

Mastering the Art of Table Gala

 Fri, 12 Dec at 06:00 pm Tanner Hall USD 215 to 589

Putting with Purpose

 Thu, 13 Nov at 06:00 pm PopStroke (Hamlin-Winter Garden)

Vision Boarding Workshop

 Wed, 05 Nov at 06:00 pm Healthy West Orange USD 5

Fish 'N' Brits Present - The Elevenses Experience

 Tue, 11 Nov at 08:00 pm Two Bridges Pub USD 31

Journey into the Uplands Guided Hike

Sat, 15 Nov at 09:00 am Oakland Nature Preserve

Oranges & Ornaments: A Festival of Trees (Saturday)

 Sat, 22 Nov at 11:30 am 21 E Plant St USD 18

Venardos Circus - Winter Garden, FL

 Thu, 20 Nov at 07:00 pm 16313 New Independence Parkway Winter Garden, FL 34787

Florida Bicycle Summit 2025

 Fri, 14 Nov at 09:00 am Tanner Hall

Best Buy Presents: Bowers & Wilkins Abbey Road Experience Tour

 Sun, 02 Nov at 06:00 pm 3367 Daniels Rd Free

Health & Harvest Festival

 Sat, 08 Nov at 08:00 am Winter Garden Farmers Market

HALLOWEEN ADULT PARTY @ VFW Post 4305 🎃👻

 Fri, 31 Oct at 06:00 pm 1170 E Plant St, Winter Garden, FL

MomCo Winter Garden Meetup #5 'Surrender Your Stress" (Downtown)

 Thu, 13 Nov at 06:30 pm 125 E Plant St, Winter Garden, FL 34787-3128, United States

Stevi Ann Designs @ Macy's Winter Garden!

 Sat, 01 Nov at 10:00 am Macy's Free

Arabella's Angels @ Macy's Winter Garden!

 Sat, 08 Nov at 10:00 am Macy's Free

Dream Big 2025

 Sat, 08 Nov at 06:00 pm 13105 W Colonial Dr, Winter Garden, FL 34787

Trick or Treat Trail

 Sat, 01 Nov at 02:00 pm 24 E. Joiner St., Winter Garden, FL

Oranges & Ornaments: A Festival of the Trees with Mrs. Claus

 Sat, 22 Nov at 08:00 am The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center USD 25

Sell your camera gear (free event) at The Lens Pal

 Fri, 14 Nov at 10:00 am The LensPal Free

Movie At The Trails - Chapin Station & Blanchard Park

 Sat, 15 Nov at 02:00 pm Chapin Station Free

ChristmasTrivia with Puzzles Entertainment

 Tue, 02 Dec at 07:00 pm Crooked Can Brewing Company

Holiday Cocktail Party Cooking Class

 Sun, 09 Nov at 05:15 pm The Ancient Olive Gourmet of Winter Garden USD 82

Imersão INVICTAS com Pra. Ruth Catala em Orlando

 Fri, 28 Nov at 06:00 pm 17800 Bali Blvd USD 185

Renderglow at Pilar’s Loft

 Fri, 21 Nov at 08:00 pm Pilars Loft

Arabella's Angels @ Macy's Winter Garden!

 Sat, 22 Nov at 10:00 am Macy's Free

Annual Fall Festival

 Sun, 02 Nov at 12:00 pm 15501 Towne Common Boulevard, Winter Garden, FL

AMERICAN STANDARDS — Celebrate the American Songbook and Support the First Amendment

 Sat, 08 Nov at 07:00 pm OCOM - Orlando College of Osteopathic Medicine

SMALL BUSINESS SATURDAY SIDEWALK SALE & LIVE MUSIC

 Sat, 29 Nov at 10:00 am Winter Garden Downtown Historic District

Homegrown in Horizon West Market

 Sun, 07 Dec at 09:00 am 16016 New Independence Pkwy, Winter Garden, FL, United States, Florida 34787

Invisible bead method hair extension class

 Mon, 03 Nov at 10:00 am Millionaire Hair Salon USD 2,136

Veterans Appreciation Fun Run 5K & 3rd Annual Be the One Ruck

 Sat, 01 Nov at 07:00 am 16016 New Independence Pkwy #100, Winter Garden, FL 34787

Oranges and Ornaments

 Fri, 21 Nov at 05:00 pm The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center USD 23

Give Back Parent's Night Out Bash!

 Fri, 21 Nov at 06:30 pm 13175 West Colonial Drive, Winter Garden, FL, United States, Florida 34787

Veterans Build Ceremony with West Orange Habitat for Humanity

 Fri, 07 Nov at 09:00 am Edgeway Drive Free

All Is Calm: The Christmas Truce of 1914

 Sat, 20 Dec at 07:30 pm The Garden Theatre on Plant

Sip & Glow - An Evening of Beauty, Bubbly, and Self-Care

 Sat, 15 Nov at 01:00 pm Sol Bonita Med Spa Free

Holiday Snacks & Sweets Cooking Class

 Sun, 23 Nov at 05:15 pm The Ancient Olive Gourmet of Winter Garden USD 82

Desde Crédito a Cierre: Seminario Gratuito para Compradores

 Sat, 22 Nov at 09:00 am Maxey Community Center Free

Guacamole Making Class Family Fun Little chef

 Sat, 15 Nov at 10:30 am 153 Sugar Belle Dr USD 8

Christmas Pet and Family Photo Event

 Thu, 20 Nov at 10:00 am Woof Gang Bakery & Grooming Hamlin USD 35 to 115

Eleven Eleven Custom Jewelry @ Macy's Winter Garden!

 Sun, 16 Nov at 11:00 am Macy's Free

Open Gym!

 Fri, 07 Nov at 06:30 pm 13175 West Colonial Drive, Winter Garden, FL, United States, Florida 34787

Orange and Ornaments: A Festival of the Trees

 Fri, 21 Nov at 05:00 pm The Winter Garden Heritage Foundation - Healthy West Orange Heritage and Cultural Center

Noche de Templo y Historia Familiar

 Sat, 01 Nov at 07:00 pm The Church of Jesus Christ of Latter-day Saints

Stranger Things Trivia with Puzzles Entertainment

 Tue, 04 Nov at 07:00 pm Crooked Can Brewing Company

HOLIDAY FLIX AT THE GARDEN

 Sun, 07 Dec at 02:00 pm 160 W Plant St, Winter Garden, FL 34787-3143, United States

Stevi Ann Designs @ Macy's Winter Garden!

 Sat, 13 Dec at 10:00 am Macy's Free

Arabella's Angels @ Macy's Winter Garden!

 Sat, 20 Dec at 10:00 am Macy's Free

Homegrown Market in Horizon West

Sun, 02 Nov at 09:00 am 16016 New Independence Pkwy, Winter Garden, FL, United States, Florida 34787

MomoCo Winter Garden Christmas Party

Sun, 07 Dec at 03:00 pm 125 E Plant St, Winter Garden, FL 34787-3128, United States

All is Calm: The Christmas Truce of 1914

 Sun, 21 Dec at 02:00 pm 160 W Plant St, Winter Garden, FL 34787-3143, United States

Kids Bike Rodeo 2025 - Winter Garden

 Sat, 15 Nov at 09:00 am Plant Street Winter Garden, Fl

America's Fleetwood Mac Experience

 Fri, 14 Nov at 07:00 pm Horizon High School Performing Arts Center USD 35 to 45

Jingle & Mingle Late Night Shopping

 Thu, 06 Nov at 05:00 pm 24 E. Joiner St., Winter Garden, FL

HERO DAY

 Sun, 09 Nov at 09:00 am 100 Windermere Rd, Winter Garden, FL, United States, Florida 34787

BLUE COLLAR APPRECIATION DAY @ POST 4305 🚜🛠️🦺🧰

 Fri, 07 Nov at 12:00 pm 1170 E Plant St, Winter Garden, FL

November Dillard Street Elementary PTA Meeting

Thu, 06 Nov at 05:30 pm 311 N. Dillard, Winter Garden, FL, United States, Florida 34787

ABC Winter Garden Premium Wine Tasting Experience

 Wed, 05 Nov at 05:30 pm ABC Fine Wine & Spirits USD 16

Maxey PTA Meeting and Yoga on the Lawn

 Wed, 05 Nov at 05:00 pm 602 E. Story Rd, Winter Garden, FL, United States, Florida 34787

Fall Festival Vendor Fair

 Sun, 02 Nov at 12:00 pm 15501 Towne Common Boulevard, Winter Garden, FL

Guacamole Making Class Family Fun for Little chef

 Sat, 13 Dec at 10:30 am 153 Sugar Belle Dr USD 8

November Evening Yoga led by CFPY at LiveTrends Boutique

 Tue, 11 Nov at 06:00 pm LiveTrends Boutique USD 25

Open Gym!

 Fri, 05 Dec at 06:30 pm 13175 West Colonial Drive, Winter Garden, FL, United States, Florida 34787

November Mahjong Open Play at LiveTrends Boutique

 Tue, 18 Nov at 06:00 pm LiveTrends Boutique USD 36

Veteran Taproom Takeover

Tue, 11 Nov at 06:00 pm Home State Brewing Co.

Winter Garden Elks Veterans Golf Classic

Fri, 07 Nov at 08:00 am Stonybrook West Country Club

Christmas Breakfast with Anna and Olaf

 Sat, 06 Dec at 09:00 am UNO Pizzeria & Grill USD 48

Winter Garden PAL Donut Dash 5K

 Sat, 08 Nov at 08:00 am 1 Surprise Dr, Winter Garden, FL 34787-2339, United States

Dream Finders Homes Hippity Hop 5K

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

Member Meeting ~ Monthly

 Tue, 18 Nov at 06:00 pm The Blake at Hamlin

Ginger Bread House Family Workshop

 Sat, 13 Dec at 03:00 pm 127 S Boyd St, Winter Garden, FL, United States, Florida 34787

Rucksgiving with West Orange Ruckers

 Sun, 23 Nov at 10:00 am Newton Park

MomCo Winter Garden Christmas Meetup #6 (Downtown)

 Thu, 11 Dec at 06:30 pm 125 E Plant St, Winter Garden, FL 34787-3128, United States

Night 0: Pilar's Pre

 Thu, 15 Jan at 06:00 pm Pilars Martini & Loft Free

Live Well in Horizon West

Sun, 18 Jan at 09:00 am 16016 New Independence Pkwy, Winter Garden, FL 34787-8153, United States

Dream Finders Homes 12Ks and 5Ks of Christmas

 Sat, 20 Dec at 07:30 am Cinepolis Hamlin

Member Meeting ~ Monthly

 Tue, 16 Dec at 06:00 pm The Blake at Hamlin

Veteran's Benefits Day

 Tue, 04 Nov at 10:00 am 271 W Plant St, Winter Garden, FL, United States, Florida 34787

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

 Fri, 30 Jan at 09:00 am The LensPal Free

Eleven Eleven Custom Jewelry @ Macy's Winter Garden!

 Mon, 22 Dec at 10:00 am Macy's Free

Bone Voyage

 Thu, 06 Nov at 06:30 pm 426 W Plant St, Winter Garden, FL 34787-3014, United States

Spirits & Sparkles After Hours Shopping

 Thu, 18 Dec at 05:00 pm 24 E. Joiner St., Winter Garden, FL

OCPN City Gathering | November 2025

 Wed, 12 Nov at 12:00 pm Mosaic Church Free

2026 All-American Exposure Bowl-Orlando

 Sun, 18 Jan at 08:00 am West Orange High School USD 19

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

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

November 2025 IronMen of God Coffee

 Fri, 21 Nov at 07:00 am Pilars Loft

2025 Ministers Meeting

 Thu, 06 Nov at 09:00 am 943 W Story Rd, Winter Garden, FL, United States, Florida 34787

OCPN City Gathering | December 2025

 Wed, 10 Dec at 12:00 pm Mosaic Church Free

Complimentary Fall Prevention Education Class

 Thu, 04 Dec at 01:00 pm 12323 W Colonial Drive, Suite 140 Winter Garden, FL 34787

Fairy Hair - Winter Garden - The Summit

 Mon, 10 Nov at 10:00 am The Summit of Winter Garden

Handtied Hair Extension Hands On Class Orlando

 Mon, 01 Dec at 10:00 am Millionaire Hair Salon USD 4,163

Fairy Hair - Winter Garden - The Summit

 Mon, 08 Dec at 01:00 pm The Summit of Winter Garden

Night Owl Art Club

 Wed, 02 Apr at 09:00 pm Lucky Straws Boba Tea Cafe Free
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