Local Events 
in Winter Garden Florida

Welcome to the best Winter Garden Events listings online! We aim to be the best source of Winter Garden events, concerts, live music, festivals, parades and other entertainment events by consolidating everything into one list, with events listed in chronological order. If you have a big event you would like to see listed here, let us know! Winter Garden Events, Winter Garden FL 34787 Events.

Here is a list of our yearlong events in
Winter Garden for 2022

Recurring Events

Winter Garden plays host to a multitude of events each week. Whether it is lively music you are after, or a trip down memory lane in your favorite antique muscle car we have what you are looking for. Take the vegetables from the farmer's hands right to your table, or talk shop with a real car buff. Come enjoy yourself at these free events. Winter Garden, FL 34787 events

Fridays on the Plaza Concert Series 2023
When: Every Friday
Time: 7:00pm - 9:00pm
Where: Centennial Park Gazebo, 56 W. Plant Street

January 6- Porchdogs (Cajun, Zydeco)
January 13- Grimes Alley (Country, Blues)
January 20- Katy Flanders (Acoustic, Blues) 
January 27- Retro Ramblers (Oldies)
February 3- Tree Frogs (Classic Hits, 70's & 80's)
February 10- Brian & Hannah (Pop, Jazz)
February 17- Amy Robbins (American Folk, Acoustic)
February 24- Mountain Brew (Country, Bluegrass)
March 3- Southbound Duo (Bluegrass, Folk)
March 10- Crenshaw (Folk)
March 17- Salted Vine (Pop & Rock, 60's to today)
March 24- Orlando Gentleman of Jazz (Jazz)
March 31- Rowdy Jameson Band (Country)

Farmers Market 2023
When: Every Saturday
Time: 8:00am - 1:00pm
Where: City Pavilion, 104 S. Lakeview Ave.
Historic Downtown Winter Garden

Open for business

Cruz-n-Car Show
Time: 4:00pm - 8:00pm
Where: Downtown Winter Garden on Plant Street


Special Events


Martin Luther King, Jr. Celebration
Parade & Live Concert
When: Monday, January 16, 2023 
Time: 10:00 am – 4:00 pm
Where: Downtown Pavilion, 104 S. Lakeview Avenue 
Commemorate the life and legacy of Dr. Martin Luther King, Jr. with a community celebration! The event includes a parade, a lineup of live music performances, family friendly activities, displays, and food vendors.
This signature City event kicks off at 10:00 am with a Dr. Martin Luther King, Jr. Celebration Parade along Plant Street. 
To participate in the parade, preregistration is required due to limited space. To submit registration online, click here. To print form and return to Winter Garden Parks & Recreation Department, click here. Parade entry applications must be received no later than Tuesday, January 10, 2023, and will not be accepted after that date. All applicants will receive an email notification stating whether they are approved or not approved. All entries are eligible for the Parade Spirit Award.
For those wanting to watch the parade, bring a lawn chair or blanket and head to your favorite viewing spot along Plant Street (from Woodland St. to Central Ave.). 
Immediately following the parade at about 10:30 am, the celebration continues with a lineup of top-notch music performances at the Downtown Pavilion. The Gerry Williams Band, Craig Thompson Project, and Selwyn Birchwood will be taking the stage throughout the day with the event concluding at 4:00 pm.
For more information, please contact Winter Garden Parks and Recreation Department: 
(407) 656-4155, recinfo@cwgdn.com, 310 North Dillard Street.


Winter Garden Heritage & Music Festival
Celebrating the City's 120th Anniversary
Saturday, February 11, 2023
Historic Downtown on Plant Street

Established in 1903, the City of Winter Garden commemorates its heritage with a special 120th anniversary extravaganza. Festivities include six stages of entertainment, strolling performers, and much more! 
This Winter Garden Heritage & Music Festival is a FREE event for all ages and is brought to you by the City of Winter Garden along with the Winter Garden Heritage Foundation and other generous partners.
Live Music & Entertainment, 11:00 am - 10:00 pm
Simultaneous and continuous performances will be held at various outdoor stages throughout historic downtown stretching from Central Avenue to Dillard Street. The entertainment kicks off at 11:00 am and continues nonstop through 10:00 pm. 
For Full List of Activities for this Event Click Here...


Shop, Dine & Stroll 2023
When: Saturday, March 25
All Day
Where: Historic Downtown Winter Garden on Plant Street
Outdoor Shopping & Dining Experience with LIVE MUSIC in picturesque Historic Downtown

Winter Garden in celebration of the annual National Mom and Pop Business Owners Day!

Live Music
Music will fill the air as you Shop, Dine & Stroll when a special live music performance by Breezeway Trio takes center stage from 4:00 pm to 7:00 pm. Grab a nearby swing, bench or outdoor table, or bring your own chair for a front row seat. Don't get too comfortable because the band's jazz tunes will have you on your feet dancing!
-Breezeway Trio Live Music Performance, 4:00 - 7:00 pm
-Centennial Plaza Gazebo, Historic Downtown
Shop, Dine & Stroll will be held rain or shine. Operating hours, sales, and special offers vary per merchant. Participation is at the discretion of the individual retail establishments.
For more information...

Evening at the Pops 2023
When: Saturday, March 25, 2023
Where: Newton Park, Winter Garden
Bring a blanket or chair and enjoy an outdoor concert under the stars performed by the Space Coast Symphony Orchestra. Newton Park at the shore of Lake Apopka provides a stunning backdrop for this outdoor concert. This is a ticketed event.
An Instrument Petting Zoo for children will kick off the event at 4:30 pm.
Space Coast Symphony will perform starting at 6:00 pm
The event will be held at Newton Park, 31 W. Garden Avenue, in Winter Garden.
Ticket Prices:
General Admission: $10 per person (online and at the door)
Children 8 and under are Free
VIP: $75 per person (includes reserved seating, dinner, drinks and live entertainment by HAPCO Music Foundation at adjacent Tanner Hall). Available through online purchase only.
For more information and to order tickets...


21st Annual Spring Fever in the Garden 2023
When: Saturday, April 1 & Sunday, April 2
Where: Historic Downtown Winter Garden on Plant Street
Hosted by the Bloom & Grow Garden Society of West Orange County, in conjunction with the City of Winter Garden, the 21st Annual Spring Fever in the Garden is a coveted event for locals and visitors alike. A variety of gardening vendors line the downtown streets with entertainment and activities for all ages to enjoy.

Festival Highlights:
-Chalkin’ It Up Sidewalk Art Contest
-Live Entertainment
-Kid Zone Area
-Nature-related Arts and Crafts
-Ask the Experts Booth
-Avian Reconditioning Center Birds of Prey
-Vendor Booths selling thousands of a wide array of flowers and foliage
-And more!

For entertainment schedule, event virtual map, parking information, and other event logistics, visit www.springfeverinthegarden.org.

The annual chalk art contest is one of the most popular events of the festival! Contestants of all ages bring the area in front of City Hall to life with nature-related art. Stroll by and see their creativity in action. The contestants can start at daybreak and judging takes place at 4:00 pm. The amazing creations will remain for viewing throughout the weekend, weather permitting.
The contest is free to enter and prizes will be awarded. Contestants must bring their own chalk and supplies. Space is limited and registration deadline is March 17, springfeverinthegarden.org/chalk.
Saturday, April 1 │ Contest, 6:00 am - 4:00 pm (Judging) / Viewing, All Day
Sunday, April 2 │ Viewing, All Day
City Hall, 300 W. Plant Street
Booths and activities geared to children with fun ways to learn about nature and the environment. There will be craft making, face painting, balloon animals, a juggler, and more!
Music will fill the festival air with an eclectic group of entertainers performing throughout the day.
Seize the opportunity to get your questions answered by some of the best horticulturalists and nursery people in Florida.
See owls and raptors up close and learn about Florida’s magnificent birds of prey and their natural habitats. The Center specializes in raptor reconditioning and education.
Spring Fever in the Garden will take place rain or shine. The Bloom & Grow Garden Society is proud to have Orlando Health as its 2023 presenting sponsor.


Winter Garden Memorial Day Service 2023
When: Pending...
Time: 8:30am
Where: Veterans Memorial Park
420 S. Park Ave.
Winter Garden, FL 34787
Former City Commissioner Theo Graham will be the master of ceremonies for teh 26th year, and Mayor John Rees will also be participating. The guest speaker will be Robert E. Cole, Jr., a Winter Garden resident and retired master sergeant of the U.S. Air Force. The program will also include patriotic music by Geoff Bashioum, a color guard made up of members iof the Winter Garden police and fire departments, a roll call of the war dead and a wreath-placing ceremony. For more info contact: Theo Graham at 407-656-2021




Celebrate Fourth of July all weekend long in Downtown Winter Garden!

Friday, JULY 1: Red, White & Blues on the Plaza, a live music performance from 7:00pm-9:00pm in the center of downtown. 

Saturday, JULY 2: Farmers Market Independence Day Celebration from 8:00 am-1:00 pm. Visit the patriotic-decorated market for some good old-fashioned fun including live music, kids' crafts, lawn games, and one-stop shopping for your holiday barbecue. Donwtown Pavilion, 104 S. Lakeview Ave.

Monday, JULY 4: Annual All American Kids Parade & Pancake Breakfast- Decorate your bike, scooter, or wagon and join us for a Red, White and Blue stroll through Downtown Winter Garden. Located at the Winter Garden Masonic Lodge, the complimentary Kids Pancake Breakfast starts at 8:00 am and the Parade Line-Up begins at 9:45 am for the 10:00 am Parade.

Party in the Park, July 4 starting at 6:00pm. Keep your eyes on the sky for one of the best firework displays in West Orange County. Live music, games, crafts, food, vendors, and fun for all ages! Parking available at several locations on North Dillard Street. Bring a chair, blanket, or have a seat on the grass for this annual Winter Garden tradition! No personal fireworks nor alcohol permitted.

On the evening of JULY 4, bring a chair or blanket to celebrate the holiday with a FIREWORKS DISPLAY on Lake Apopka at Newton Park starting at 9:15 pm.

Parking available at Health Central Park and Dillard Street Elementary.  Firework display at 9:15pm. In case of a potential rainout please call the rainout hotline number at 407-877-5432.




October 21 – October 31, 2022
Historic Downtown Winter Garden

Halloween is celebrated for 11 days – not just one -- in Winter Garden! The City’s Halloween Experience provides family-friendly festivities in Downtown Winter Garden, including seven nights of an outdoor animated Halloween Light Show on City Hall; a hay maze; fall- and spooky-themed photo locations, decorations and light displays throughout downtown; a Spooky Caboose; a Halloween Celebration at the fall-themed Farmers Market; a Downtown Harvest Sidewalk Sale & Stroll; and more! Costumes are welcome any day!

•Hay Maze at City Hall
•Fall-Themed Photo Stations
•Seasonal Decorations & Light Displays
•Unique Stores & Restaurants to Shop, Dine & Stroll surrounded by historic charm and holiday ambiance
•Expanded Outdoor Patios to dine amidst the Halloween Experience while enjoying the weather

All events and activities are FREE, unless noted otherwise.

A Halloween animated light show synchronized to music projected onto the front façade of City Hall.

October 21, 22, 23, 28, 29, 30, 31 | 7:00 – 9:00 pm

City Hall, 300 W. Plant Street

Shop the outdoor sidewalk sale surrounded by the spooky and fall-themed Halloween Experience ambiance. Stores will feature special sales, promotions, and seasonal merchandise. It is a great time to purchase for the new season while getting a head start on holiday shopping. The unique shops of downtown feature apparel, jewelry, home décor and greenery, cycling/running/sporting equipment and accessories, gourmet foods, health and beauty products, pet supplies, furniture, and much more. In addition, a number of downtown restaurants will feature seasonal menus and promotions to enjoy while dining at the outdoor patios surrounded by Halloween nirvana.

Saturday, October 22 | Daylong
Historic Downtown

Saturday, October 29 - Hotel Transylvania, 3:00 pm
Saturday, October 29 - Psycho, 7:30 pm
Sunday, October 30, Hocus Pocus, 2:00 pm

Garden Theatre, 160 W. Plant Street
Purchase tickets at www.gardentheatre.org/movies.

Come out to the market for some Halloween fun at the fall festively decorated Farmers Market. There will be a special Halloween craft to make and take home at the KidZone tent (located next to the Parking Garage on Tremaine Street) as well as live music, and family-friendly games on the lawn.

Pumpkin, pumpkins, and more pumpkins -- of all shapes and sizes – can also be found at the Farmers Market. Get your gourds, fresh fall harvest produce, seasonal décor, and lots of treats to make your Halloween and fall holidays special.

Every Saturday | 8:00 am – 1:00 pm
Saturday, October 29 | Halloween at the Market
Downtown Pavilion, 104. S. Lakeview Ave

Enter the Spooky Caboose – if you dare -- stationed outside the Winter Garden History Center. The spooky-decorated caboose has fun frights for all ages. Free to enter. Donations appreciated.

Monday, October 31 | 3:00 – 8:00 pm
Winter Garden History, Education, and Visitors’ Center, 21 E. Plant Street

A variety of outdoor street performers will delight audiences as they stroll, shop, and dine. You just never know what pop-up surprises await!

October 21, 22, 23, 28, 29, 30, 31 | Evenings

You will be amazed as you work together to transfer a prepared cereal box on a base into an awesome “Haunted House.” All materials and step-by-step guidance are provided. This popular family event fills up quickly! Click here to register.. Questions, call 407-347-7996.

Saturday, October 22 | 4:00 - 5:30 pm
$30 per house for 1 adult with 1 child
SOBO Art Gallery, 127 S. Boyd Street


Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening

Harvest Sidewalk Sale & Stroll Downtown, Daylong
Fall themed Winter Garden Farmers Market, 8:00 am – 1:00 pm
Create a Haunted House Family Event, SOBO Art Gallery, 4:00-5:30 pm. $30 fee for 1 adult/1 child.
Register at www.wgart.org/kids.
Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening

Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening

Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening

Halloween at the Market – holiday kids craft and special programming at the fall-themed Winter Garden Farmers Market, 8:00 am-1:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening
Halloween Movie Series at the Garden Theatre, Hotel Transylvania, (2012, PG) 3:00 pm
Purchase tickets at www.gardentheatre.org/movies
Halloween Movie Series at the Garden Theatre, Psycho, (1960, R) 7:30 pm
Purchase tickets at www.gardentheatre.org/movies

Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening
Halloween Movie Series at the Garden Theatre, Hocus Pocus, (1993, PG) 2:00 pm
Purchase tickets at www.gardentheatre.org/movies

Spooky Caboose at the History Center, 3:00-8:00 pm
Halloween Light Show on City Hall, 7:00-9:00 pm
Street Performances & Surprises, Evening
Halloween Experience is hosted by the City of Winter Garden to provide a fun way to celebrate the holiday while providing opportunities to support local businesses.

Convenient parking is always free throughout Downtown Winter Garden, including at the City’s three-level parking garage (160 S. Boyd St.) and the new 117-space parking lot (37 N. Boyd St.).


•HARVEST SIDEWALK SALE & STROLL | Saturday, October 22
•HEALTH & HARVEST FESTIVAL | Saturday, November 12
•HOLIDAY BOUTIQUE STROLL | Thursday, December 8
•TIS THE SEASON | 38 days of Merry in Winter Garden | December 2-January 8


Small Business Saturday Sidewalk Sale
When: Saturday, November 26. 2022
Kick off the holiday shopping season at the annual Downtown Winter Garden Small Business Saturday Sidewalk Sale. The mom-and-pop shops in historic downtown make this a must stop to observe the national holiday. Stroll and shop the outdoor sale racks in the festive-decorated historic district. Be sure to pop inside for additional promotions and special savings.


Tis the Season Schedule 2022
When: December 22-January 8, 2022
Downtown Winter Garden transforms into a winter wonderland for 38 days of Tis the Season! Click HERE to learn more about all the free downtown holiday happenings and the seasonal resident programs to make merry memories!

Light Up Winter Garden
When: Friday, December 2, 2022
Time: 6:00-9:00pm (Lighting at 6:15pm)
Location: City Hall, 300 W. Plant Street (Lighting) and throughout Historic Downtown
Join us to welcome the holiday season with this annual event to kick off our 38 days of Tis the Season. The lighting will take place at 6:15 pm at City Hall followed by various activities for all to enjoy. Sponsored by Duke Energy and the City of Winter Garden.

Winter Garden Christmas Parade
When: Saturday, December 3, 2022
Time: 10:00am
Where: South Dillard Street & Plant Street, Historic Downtown
Bring a lawn chair or blanket and head to your favorite spot for this annual event. A long-standing Winter Garden holiday tradition will delight spectators and bring in holiday cheer! Don't forget to look for the Big Guy himself at the end of the parade!

Holiday Boutique Stroll
When: Thursday, December 8, 2022
Time: 5:00-8:00pm
Where: Historic Downtown Winter Garden
Holiday shopping at its finest with a stroll of the boutiques of Downtown Winter Garden to find unique presents while enjoying light refreshments, raffles, outdoor/indoor specials and promotions at participating boutiques. While perusing the outdoor racks and strolling through festive downtown, you will find colorful sights and sounds with enchanting decorations and light displays and holiday music in the air – reminisce of a Hallmark holiday movie!
The festively decorated stores and downtown area truly make it a perfect evening for gift buying.

De-light-Ful Decorations Contest 2022
Judging: Tuesday, December 13 and Wednesday, December 14 at 5:30pm.
Drag out the lights, hang up the garland, put up the glowing Santa and enter your home to win! Festive presentations of outdoor decorations could win up to $100! Winning displays will be posted on the City’s website. For more information about this event, click HERE.

Winter Garden Fire Rescue Annual SANTA RUN 2022
"Santa Claus is Coming to Town!"
The Winter Garden Fire Rescue annual “SANTA RUN” brings Santa and his sleigh through neighborhoods within city limits! This moving parade takes place on select nights as Santa -- along with elves of firefighters, police, and City staff-- spread holiday music, treats, and good cheer along the way.
Santa will be in the following areas from 5:45 − 9:00 pm on the following dates:
• Monday, December 12 − North West Winter Garden
• Tuesday, December 13 − North East Winter Garden
• Wednesday, December 14 − South Winter Garden: CR 545 Corridor (West Side)
• Thursday, December 15 − South Winter Garden: CR 545 Corridor (East Side)
• Friday, December 16 − South Winter Garden: CR 535 / Daniel’s Road Corridor
• Saturday, December 17 − South Winter Garden: Beulah / Windermere Road Corridor
An alternate date is scheduled for December 19 if weather interrupts one of Santa’s visits.
For for information click HERE.

Watch video from Santa Run 2014...

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Martin Luther King 2023

Martin Luther King, Jr. Celebration
Parade & Live Concert
When: Monday, January 16, 2023 
Time: 10:00 am – 4:00 pm
Where: Downtown Pavilion, 104 S. Lakeview Avenue 

Shop Dine & Stroll 2023

Shop, Dine & Stroll
March 25, 2023

Evening at the Pops 2023

Evening at the Pops
March 25, 2023

Spring Fever in the Garden 2023

Spring Fever in the Garden
April 1 & 2, 2023


July 2: 7-9pm Red, White & Blues on the PLaza

July 3: 8am-1pm Farmers Market Independence Day Celebration

July 4: 8am & 10am All American Pancake Breakfast & Kids Parade

July 4: 9:15pm Fireworks at Newton Park



Welcome the Christmas Season with the Annual Light Up Winter Garden event downtown. Live entertainment, vendors, shopping and children’s activities. Friday, December 6:00-9:00pm with Street lighting ceremony at 6:15pm.


Downtown Winter Garden beginning at S. Dillard & Plant Street, Saturday, December 3, 2022 at 10:00am. Parade continues to Historic Downtown Winter Garden on Plant Street.

Winter Garden's Annual
Santa Run

December Pending...

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