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.

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

January 5- Retro Ramblers (Oldies, Pop)
January 12- Layla Brisbois (Acoustic Hits)
January 19- Tree Frogs (Classic hits, 60’s & 70’s)
January 25- Good Times Jazz Band (Jazz)

February 2- Grimes Alley (Blues, Country, Acoustic Unplugged)
February 9- Da Capo Jazz Trio (Jazz)
February 16- Scotty Long (Folk, Country, 60’s to today)
February 23- Good Times Jazz Band (Jazz)

March 2- Amy Robbins (American Folk, Country)
March 9- Molly Holton (Acoustic Blues)
March 16- Backyard Band (Electric Fusion, Bluegrass)
March 23- Good Times Jazz Band (Jazz)
March 30- Porchdogs (Cajun, Zydeco)

April 6- Bob & Patty Tatum (Pop, Acoustic)
April 13- Crenshaw (Folk)
April 20- Jade Frances (Pop, Acoustic)
April 27- Good Times Jazz Band (Jazz)

Farmers Market
When: Every Saturday
Time: 9:00am - 2:00pm
Where: City Pavilion, 104 S. Lakeview Ave.
Historic Downtown Winter Garden

Cruz-n-Car Show
Now being held quarterly
When: Saturday Jan. 20, April 21, June 16, Sept. 15, 2018
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

Martin Luther King, Jr. Celebration
When: Saturday, Jan. 13, 2018
Time: 1:00pm-4:00pm
Where: Orlando Magic Recreation Center, 309 S. West Crown Point Rd.
Come celebrate and honor this great leader of the civil rights movement. Enjoy entertainment, speakers, vendors, kids’ activities and much more! A community march will travel from East Bay Street to the Orlando Magic Gym. To participate in the march, please meet at 118 E. Bay Street at 12:30pm. For more info call: 407-656-4155

Little Cupid’s Carnival
When: Tuesday, Feb. 14, 2017
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.

7th Annual Winter Garden Blues & BBQ
When: Saturday, February 10th, 2018

Time: 4:00pm-10:00pm
Where: Downtown Pavilion, 104 Lakeview Avenue

FREE Admission • BBQ, Beer and Wine available for purchase.
This festival pairs the hottest Blues and Roots musicians with award winning local BBQ connoisseurs, for an afternoon celebration of true Southern Soul. An exciting annual event that is not to be missed! For more info call: 407-656-4155
4:00pm-Ari & The Alibis
6:00pm-Doug Deming & The Jewel Tones
8:00pm-Albert Castiglia

Evening at the Pops
When: Saturday, March 25, 2017
Time: 6:30pm-8:30pm with Petting Zoo at 4:30pm
Where: Newton Park, 29 West Garden Avenue
The Rotary Club of Winter Garden presents the Annual Evening at the Pops event, featuring the Orlando Philharmonic Orchestra.  Sit under the stars and enjoy the symphony! There will be an instrument petting zoo at 4:30pm and the orchestra will perform at 6:30pm on the shores of Lake Apopka.
Fee: $10 a Ticket / $5 Children 12 years or younger.
For more info: www.facebook.com/EveningAtThePops

Winter Garden Lions Club Annual Easter Egg Hunt
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.

Spring Fever in the Garden
When: Pending...
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: Saturday April 21, 2018
Time: 4:00pm - 8:00pm
Where: Downtown Winter Garden on Plant Street
With music by WJBJ Cruisin' with the Classics

Fun Ballroom Dance Classes
When: Starting Friday, May 26, 2017
$96 per person/per Eight Week Class
Where: OAKLAND at Center for Dance and Performing Arts
301 South Tubbs St. Oakland, FL 34760
Class Schedule and Registration - CLICK HERE<<
Each 8-week class meets for one 55 minute lesson per week and
focuses on one dance for the entire 8 weeks. The cost is Always
only $96 per person for the entire 8 weeks!

Winter Garden Memorial Day Service
When: Monday, May 29, 2017
Time: 8:30am
Where: Veterans Memorial Park
420 S. Park Ave.
Winter Garden, FL 34787
PENDING INFO... U.S. Navy Captain Frank Winget, a SEAL veteran for more than 30 years, is the featured speaker at this year's Memorial Day Service. A Roll Call of Veterans and a placement of wreaths will be presented with patriotic songs performed as we invoke pride, honor and respect for our veterans. Refreshments will be served. For more info contact: Theo Graham at 407-656-2021.

Oakland Arts and Music Festival
When: Saturday, June 10, 2017
Time: 2:00pm - 8:30pm
Where: Town of Oakland Town Center
221 N. Arrington St.
Oakland, FL 34760  More Info...

Cruz-n-Car Show
When: Saturday June 16, 2018
Time: 4:00pm - 8:00pm
Where: Downtown Winter Garden on Plant Street
With music by WJBJ Cruisin' with the Classics

All American Kids Parade & Breakfast
When: Tuesday, July 4, 2017
Time: 8:00am - 11:00am
Where: Winter Garden Masonic Lodge, 230 West Bay Street downtown
Enjoy breakfast, decorations to adorn bicycles, scooters, strollers and wagons and games at the Winter Garden Masonic Lodge. The parade starts at 10:00am and breakfast is served from 8:00am-9:45am.  For more information, please call the Winter Garden History Center at 407-656-3244.

Party in the Park
When: Tuesday, July 4, 2017
Time: 5:00pm - 9:30pm
Where: Newton Park, 29 W. Garden Ave. on Lake Apopka
Bring a chair, blanket to sit on the grass for this annual Winter Garden tradition!  Keep your eyes on the sky for one of the best firework displays in West Orange County.  Live music by Speed Limit 70. Fun for all ages with family activities, food and more. 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.

Oakland Arts & Music Festival
When: Friday, August 25, 2017
Time: 4:00pm-8:30pm
Where: Oakland Town Center–221 N. Arrington Street, Oakland, FL 34760
HAPCO’s Arts & Music Festival celebrates the community of Oakland on Friday, August 25 from 4:00-8:30p at Oakland Town Center. Live music includes Pocket Change, Spayed Koolie, DaCapo Trio, NextGen Jazztet and A Cosmic Gathering Jam. There will also be food trucks, children’s activities and exhibiting artists and local businesses. Join your neighbors for an afternoon of free fun.

Cruz-n-Car Show
When: Saturday Sept. 15, 2018
Where: Downtown Winter Garden on Plant Street
With music by WJBJ Cruisin' with the Classics

20th Annual Oakland Heritage Festival
When: Saturday, October 21
Time: 9:00am to 4:00pm
Where: Speer Park in Oakland:
331 N. Tubb St. Oakland, FL 34760
The Festival is a family-oriented event with entertainment and activities for everyone including a petting zoo, silent auction, live entertainment, pollinator plant sale, Lake Apopka boat tours, merchants & concessions, human powered snow cones, history & cultural displays, historic hay ride tours, wildlife exhibits, drum circles and more! Vendor info contact: oaklandheritagefestival@cfl.rr.com.

When: Tuesday, October 31, 2017
Time: 6:00pm – 8:30pm
Where: Historic Downtown on Plant Street
Trick or Treat along Plant Street with the Downtown Merchants.Features live entertainment, local vendors and family activities. Enjoy a safe night of haunted happenings in Historic Downtown Winter Garden!

12th Annual Winter Garden Music Fest
When: Saturday, November 11, 2017
Time: Noon-11:00pm
Where: Downtown Winter Garden on Plant Street
The Winter Garden Music Fest is a FREE outdoor music celebration featuring diverse musical genres showcasing the best local talent, local food and craft beer.
Featuring performances by:
The Johnny Morgan Band
Thomas Wynn and the Believers
The Sh-Booms
Beebs and Her Money Makers
Also performing on Plant Street:
Layla Brisbois
Mud Rooster

Light Up Winter Garden
When: Friday, Dec. 1, 2017
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
When: Saturday, Dec. 2, 2017
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!

Winter Garden's Annual SANTA RUN

When: Monday, Dec. 12 through Saturday, Dec. 17, 2016
Times: 5:45pm-9:00pm
Where: A neighborhood near you!
The annual "SANTA RUN" brings Santa and his sleigh through Winter Garden neighborhoods! Click here for a schedule and map indicating when Santa visits your neighborhood!

Watch video from Santa Run 2014...

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Martin Luther King, Jr. Celebration
Saturday, January 13, 2018
1:00-4:00pm at the Orlando Magic Recreation Center
309 West Crown Point Rd.

Saturday, Feb. 18, from 4:00pm-10:00pm at the Downtown Pavilion. Great music, food and fun!

April 8 and 9, 2017
One of Florida's best plant, flower and garden festivals! Downtown Winter Garden on Plant Street.

FIREWORKS! At Party in the Park: Tuesday, July 4 from 5:00pm-9:30pm at Newton Park on Lake Apopka

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

Oct. 31: Trick or Treat along Plant Street with the Downtown Merchants. Featuring live entertainment, local vendors and family activities. Enjoy a safe night of haunted happenings along downtown Plant Street! 6:00pm - 8:30pm



Friday, December 1, 2017: 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.

Saturday, December 2, 2017: Downtown Winter Garden beginning at S. Dillard & Plant St. at 1:00pm.

Winter Garden's Annual
Santa Run

December Pending...

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