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 2022
When: Every Friday
Time: 7:00pm - 9:00pm
Where: Centennial Park Gazebo, 56 W. Plant St.

Farmers Market 2022
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


Cruz-n-Car Show 2022
When: Postponed
Time: 4:00pm - 8:00pm
Where: Downtown Winter Garden on Plant Street
With music by WJBJ Cruisin' with the Classics

Martin Luther King, Jr. Celebration 2022
When: Monday, Jan. 17
Time: Community Parade-10:00am/Celebration-10:30am-3:00pm                   
Where: Downtown Winter Garden
Come and celebrate the life and legacy of Dr. King. This community celebration will feature speeches from the community, including those by Dr. King. displays and family friendly activities. food vendors and live stage performers. including a concert throughout the day.
To kick off the celebration, there will be a Dr. Martin Luther King, Jr. Celebration Parade along Plant Street all are welcome to participate.  For more info call: 407-656-4155
Celebration Schedule
10:00am: Parade
10:30am: The Gerry Williams Band (Funk, Soul, Rhythm)
11:00am: Welcome by City of Winter Garden Mayor John Rees
11:15am: The Gerry Williams Band cont.
12:15pm: Anthony Hodge presents Martin Luther King Jr. Speech (minister and founder of Lost Sheep Ministry in East Winter Garden)
12:30pm: Corrinne Thompson (Saxophonist Solo)
1:00pm: Nick Melvin (R&B Acoustic Soul)
2:45pm: Selwyn Birchwood (American Blues guitarist, vocalist, and songwriter)
Location: Downtown Pavilion, 104 S. Lakeview Avenue


Little Cupid’s Carnival 2022
Time: 10:00am-12:00pm
Where: Location: Jessie Brock Community Center, 310 North Dillard St.
A special sweetheart filled morning for children ages 3 to 5!  Join the Parks and Recreation Department for arts & crafts, fun games, face painting and more!  Bring a friend or group.  Group headcounts are required in advance.  Please call the Recreation office with your headcount at 407-656-4155.

Annual Windermere Fine Art Show 2022
When: Pending...
Time: Sat.: 1:00pm-6:00pm & Sun.: 9:00am-5:00pm
Where:Downtown Windermere on Main Street
Join us as we promote the Fine Arts in our beautiful town of Windermere amongst the lakes. Attendance is free, so eat and drink while you buy incredible art work from our selected 85+ artists. This boutique art show features talented artists from around the country & has proven to be an annual favorite. Support us as we give back to local charities supporting those in need. For more info contact: 407-808-0665
Artists & Sponsor applications contact Anne 407-448-0244


Evening at the Pops 2022
When: TBD
Time: 6:30pm-8:30pm
Where: Newton Park, 29 West Garden Avenue
The Rotary Club of Winter Garden presents the Annual Evening at the Pops event, featuring the UCF Philharmonic Orchestra.  Sit under the stars and enjoy the symphony! The orchestra will perform at 6:30pm on the shores of Lake Apopka.
Fee: $10 a Ticket / Children under 10 Free Admission.
For more info: www.facebook.com/EveningAtThePops


Winter Garden Lions Club Annual Easter Egg Hunt 2022
When: Pending
Time: 10:30am-12:00pm
Where: Newton Park, 29 W. Garden Ave.
The Winter Garden Lions Club will be hosting their annual Easter Egg Hunt at Newton Park on Lake Apopka.  This event is FREE to the public for children ages 2 to 12.  Spare eggs will be available for children under 2. For children attending with special requirements, please contact the Recreation Office at 407-656-4155 at least one week prior to the event.

19th Annual Spring Fever in the Garden 2022
When: Saturday, April 2 and Sunday, April 3
Times: Saturday: 9:00am-5:00pm and Sunday: 11:00am-4:00pm
Where: Historic Downtown on Plant Street
This annual event in downtown Winter Garden is one of Florida's best plant, flower and garden festivals! There will be live entertainment, food vendors and thousands of plants and flowers for sale.
The festival also features "KidZone" with fun environmental education booths, photos, crafts and more!  There will be an Art Auction located in the Police Department building, the "Chalkin' It Up" sidewalk art contest, and the "Ask the Expert" booth, along with many more activities.
Free shuttle service will be available from Veteran's Memorial Park, 420 S. Park Ave.
For more information visit: www.springfeveringarden.com
Hosted by the Bloom and Grow Garden Society & the City of Winter Garden


Winter Garden Memorial Day Service 2022
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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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


Saturday, November 26, 2022


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 12-17, 2022

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