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 2022
Now being held quarterly
When: Pending...
Time: 4:00pm - 8:00pm
Where: Downtown Winter Garden on Plant Street

Take a Hike! With Oakland Nature Preserve
When: 2nd Saturday of every month
Time: 2:00pm
Where: Oakland Nature Preserve- 747 Machete Trail, Oakland
Oakland Nature Preserve Calendar


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

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


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


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



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

Friday, JULY 2: RED, WHITE & BLUES on the Plaza, a live music performance from 7:00pm-9:00pm in the center of downtown. 

Saturday, JULY 3: FARMERS MARKET INDEPENDENCE DAY CELEBRATION from 8:00 am-1:00 pm featuring a Vendor Booth Patriotic Contest, Live Music, and a Family Game Zone. 

Sunday, 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.

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.



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


Downtown Winter Garden, 300 W. Plant Street
Halloween Light Shows, Pop-Up Street Performers, Moonlight Movie, Hay Maze, Holiday-Themed Photo Stations, Halloween Decorations & Light Displays, and more!
Event schedule at www.downtownwg.com/halloween-experience-is-10-days-of-fun/

OCTOBER 22, 23, 24, 29, 30, 31
7-9 pm
Winter Garden City Hall, 300 W. Plant Street
An outdoor Halloween animated projection light show.

6:30 pm/Pre-show
7:10 pm. Movie
Downtown Pavilion, 104 S. Lakeview Avenue
City presents Monsters University (2013, G) to the community. Bring chairs and blankets for seating.

Downtown Winter Garden, 300 W. Plant Street
Outdoor sidewalk sale presented by the Downtown shops with special offers/promotions amidst Halloween and fall decorations and light displays.


Date: NOVEMBER 6  Time:8 am–10 pm
Where: Downtown Winter Garden & Surrounding Parks
In celebration of Winter Garden’s founding 118 years ago, the City of
Winter Garden and the Winter Garden Heritage Foundation will host a
daylong celebration of the community’s historic roots with old-
fashioned family fun. Exhibits and activities will provide an
opportunity to learn about the City’s history, play family-friendly
games, listen to live music (five stages), enjoy special treats, and
watch some baseball. Take a trip back in time and learn about a
community that came together to be known as Winter Garden.
For more info...

Small Business Saturday Downtown Sidewalk Sale
When:Saturday, November 27, 2021
Time: ALL-DAY, Extended Hours
Where: Downtown Winter Garden on Plant Street
Kick off the holiday shopping season at the annual Downtown Winter
Garden Small Business Saturday Sidewalk Sale. Find one-of-a-kind gifts
while enjoying special savings in a charming winter wonderland. Stroll
and shop the OUTDOOR sale racks in the festive-decorated historic
district. There will be also be in-store and online specials and


32nd Annual Light Up Winter Garden 2021
When: Friday, Dec. 3, 2021
Time: 6:00pm-9:00pm with ceremony at 6:15pm
Where: Historic Downtown on Plant Street
Join us in welcoming the season with this annual event. Live entertainment, vendors, shopping and children’s activities. Street lighting ceremony will be held at 6:15pm.

Winter Garden Christmas Parade 2021
When: To be determined...
Time: 1:00pm
Where: Begins at S. Dillard Street & Plant Street
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 Santa Claus at the end of the parade!

Due to limited space, preregistration is required for all parade entries. Parade entries will not be accepted after Friday, November 15, 2019. All applicants will receive an email notification whether approved or not approved. Parade Registration

Tis the Season Holiday Events 2021 TBD
Downtown Winter Garden transforms into a winter wonderland with all the holiday trimmings every weekend in December. Holiday Carriage Tours, Light Show on City Hall, Golf Cart Parade and more!

Winter Garden’s Annual SANTA RUN 2021
When: To be determined...
Times: 5:45pm-9:00pm
Where: A neighborhood near you!
The annual "SANTA RUN" brings Santa and his sleigh through Winter Garden neighborhoods! The Winter Garden Fire Rescue’s annual Santa Run takes Santa and his sleigh on a parade with his firefighter, police and city helpers to spread holiday music, treats and good cheer along the way.
Dec. - Santa Claus will travel through the city’s northwest.
Dec. - Santa Claus will travel through the northeast.
Dec.  - Santa Claus will travel through the west side of the 545 corridor of south Winter Garden.
Dec. - Santa Claus will travel through the east side of the County Road 545 corridor of south Winter Garden.
Dec. - Santa Claus will travel through County Road 535 and the Daniels Road corridor of south Winter Garden.
Dec. - Santa Claus will travel through Beulah Road and Windermere Road corridor of south Winter Garden.
(The rain makeup date is ....).
For more information call the Winter Garden Fire Rescue Department headquarters at 407-877-5175

Watch video from Santa Run 2014...

Christmas Golf Cart Parade 2021
When: To be determined...
Time: 4:00pm-7:00pm
Where: Along the historic streets of Winter Garden! Lineup starts at Bradford Park, 220 W. Division St., Winter Garden.
Neighbors can enjoy the parade from their front porch. The golf carts will travel along golf-cart approved streets and end at the north end of the Walker Field baseball fields at Smith Street and Park Avenue.
Participants should bring a minimum $45 donation (per cart), cash or check, for the West Orange Junior Service League, which will distribute the funds between the Edgewood  Children’s Ranch and other West Orange charities. For details and to register, go to the group’s Facebook page: Christmas Golf Cart Parade. Trailers, alcohol and candy are not allowed.

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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

Third Saturdays
January, April, June & September
from 4:00pm-8:00pm
downtown on Plant Street


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

TBD: Downtown Winter Garden beginning at S. Dillard & Plant St. at 1:00pm.

Winter Garden's Annual
Santa Run

December TBD

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