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 2025

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 2025
When: Every Friday
Time: 7:00pm - 9:00pm
Where: Centennial Park Gazebo, 56 W. Plant Street

January 3- Francesca Tarantino (Acoustic, Soft Rock, Pop)
January 10- The Lynne Gibson Project (American Roots, Bluegrass)
January 17- Retro Ramblers (Oldies)
January 24- Amy Robbins Duo (Country, Blues & Pop)
January 31- Orlando Gentleman of Jazz (Jazz)

February 7- Moon & Rayne (Alternative Rock, Pop)
February 14- Allie & the Absent Trio (Top 40's)
February 21- Lynda Nelson (Country)
February 28- Sandy Back Porch Band (Bluegrass)

March 7- Phil Bonanno (Pop, Classic Rock)
March 14- Dublin Beat (Irish)
March 21- Salted Vine (Soft Rock)
March 28- Crenshaw (Folk)

April 4- Concrete & Country (Country)
April 11- Amanda & Steve (Acoustic, Covers)
April 18- Alana Cavanaugh (Acoustic, Covers)
April 25- Old School Orlando (Classic Rock, Oldies)

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

Cruz-n-Car Show
SUSPENDED UNTIL FURTHER NOTICE
But watch video from past shows:

WINTER GARDEN EVENTS

Special Events

January

Dr. Martin Luther King, Jr. Community Celebration
Parade, Live Concert & Children's Activities
When: Monday, Jan. 20, 2025
Time: 11:00am - 4:00pm
Where: Downtown Pavilion, 104 S. Lakeview Avenue
Parade: Downtown Winter Garden on Plant Street (Kicks off at 11:00am).
Entertainment & Festivities: Downtown Pavilion, 104 S. Lakeview Ave. (11:30am - 4:00pm)
FREE
More Information...

February

Winter Garden Music Festival 2025
Saturday, Feb. 22, 2025
11:00am - 10:00pm
Downtown Winter Garden on Plant Street
FREE/Rain or Shine!
Multi-Stage outdoor concert featuring a variety of live entertainment and music genres performing continuously, along with strolling performers throughout downtown.
Brought to you by the City of Winter Garden, this FREE multi-stage outdoor concert features a variety of live entertainment and music genres performing continuously and simultaneously for 11 hours throughout historic downtown. Plus, Strolling Performers throughout downtown.
More Information...

March

Shop, Dine & Stroll 2025
When: PENDING...
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 2025
When: Saturday, March 29
Where: Newton Park, Winter Garden
Time: 6:00pm-9:00pm
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.
The event will be held on Saturday, March 23, weather permitting. There is a Rain Date of Sunday, March 24, planned just in case.
LIVE CONCERT & ACTIVITIES
•Space Coast Symphony Orchestra: Immerse yourself in the enchanting melodies performed by the talented Space Coast Symphony Orchestra.
•John Stevens from American Idol: Witness the magic as John Stevens graces the stage with his mesmerizing vocals, delivering a performance that will leave you in awe.
•Onsite food trucks at the event selling food and drinks.
•Guests are welcome to bring a picnic basket filled with their favorite delicacies and beverages.
The event is hosted by the Rotary Club of Winter Garden and co-sponsor City of Winter Garden. Evening at the Pops is a signature fundraiser for the Rotary Club of Winter Garden to facilitate donations that go back to our local community’s nonprofit organizations.
For more information and to order tickets...

April

Spring Fever in the Garden 2025
When: Saturday, April 5: 9-5 and Sunday, April 6: 10-4
Where: Downtown Winter Garden on Plant St.
Presented by the Bloom & Grow Garden Society, in partnership with City of Winter Garden, please join us for the 22nd annual Spring Fever in the Garden festival.
The annual ode to spring event is a favorite of locals and visitors alike with gardening vendors lining the downtown streets, in addition to entertainment for all ages.
For the most up-to-date event schedule, map, and information, visit www.springfeverinthegarden.org.
The festival is a “Rain or Shine” event. There are no rain dates or do over, and Spring Fever In the Garden will be up and running on the streets of historic downtown on both April 6 & 7.
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!
CHALKIN’ IT UP SIDEWALK ART CONTEST
The annual chalk art contest is one of the most popular events of the festival! Contestants of all ages are each provided a 6’ x 6’ area in front of City Hall to bring to life with nature-related art. The contestants can start at daybreak and judging takes place at 4:00 pm. Stroll by and see their creativity in action. The amazing creations will remain for viewing throughout the weekend, weather permitting.
The contest is free to enter, but preregistration is required, and space is limited. Prizes will be awarded in numerous categories. Contestants must bring their own chalk and supplies. The registration deadline is March 15, 2024, www.springfeverinthegarden.org/chalk. Participants who register before March 10 will receive a free “Chalkin’ It Up” t-shirt. (Update 3/16/24: Registration is closed and all spots have been reserved for 2024. Come out to see all the creations!)
Saturday, April 6 │ Chalkin’ It Up Sidewalk Art Contest & Viewing / Judging at 4:00 pm
Sunday, April 7 │ Viewing, weather permitting
City Hall, 300 W. Plant Street
KID ZONE
Booths and activities geared to children with fun ways to learn about nature and the environment. There will be craft making, face painting, fairy hair, balloon animals, and more!
LIVE MUSIC
Music will fill the festival air with an eclectic group of entertainers performing throughout the day.
ASK THE EXPERTS BOOTH
Seize the opportunity to get your questions answered by some of the best horticulturalists and nursery experts in Florida.
AVIAN RECONDITIONING CENTER
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.
For more information...

May

Winter Garden Memorial Day Community Ceremony 2025
When: Monday, PENDING...
Time: 8:15am-9:30am
Where: Veterans Memorial Park
420 S. Park Ave.
Winter Garden, FL 34787
The community is invited to a Roll Call of Veterans, placement of wreaths, and patriotic songs to honor and remember our local veterans who gave their lives during times of war or while serving in the United States armed forces. Please come by to pay homage to those that made the ultimate sacrifice.

June

July

Red, White & Blue Americana Events 2025
Downtown Winter Garden turns Red, White, and Blue from Memorial Day through Independence Day, The patriotic decorations pay tribute to America’s holidays while adding nostalgia to the charm of historic downtown.
Enjoy the décor while you shop, dine, and stroll. Also, a great backdrop for capturing holiday memories in photos!
Download Flyer

20th Annual All American Kids Parade & Breakfast
When: Friday, July 4, 2025
Where: Winter Garden Masonic Lodge, 230 W. Bay St.
Time: 8:00am-10:30am
Pancake Breakfast: 8:00-10:00am (Free for kids)
Parade: Line up at 9:45am/Kickoff at 10:00am
The All American Kids Parade is a popular tradition that all ages enjoy! Don you red, white, and blue and parade through historic downtown by foot, bike, scooter, wagon, etc. Wave to family and friends as you stroll by! Or, grab a favorite curbside viewing spot and cheer on the parade as it goes by. Either way, come downtown to be a part of this great 19-year-old tradition that brings the community together to celebrate America’s birthday.
Breakfast
Before the Parade, bring the family to a Pancake Breakfast, 8:00 – 9:45 am, at the Masonic Lodge. Kids eat free and breakfast is available for adults to purchase. There is also entertainment and fun activities for the kids!
Decorate
A variety of complimentary patriotic decorations is available just outside the Lodge to decorate bikes, scooters, wagons, and even your walking shoes, courtesy of the Winter Garden Heritage Foundation.
Parade
Line up at the Masonic Lodge at 9:45 am. The Parade kicks off promptly at 10:00 am and loops around downtown’s West Plant Street. The parades lasts about 30 minutes.
Everyone is welcome to join the parade of red, white, and blue -- on bike, scooter, or foot Spectators are welcome to line the street to get a good viewing spot to cheer on the parade participants. Bring your own chair to watch in comfort.
Winter Garden Masonic Lodge No. 165 hosts this event, in collaboration with the City of Winter Garden.

Party in the Park/Fireworks Display
When: Friday, July 4, 2025
Where: Newton Park on Lake Apopka, 29 W. Garden Avenue
Time: 6:00pm-10:00pm
Fireworks Display: 9:15pm
The City of Winter Garden presents Party in the Park, one of the best firework shows in Central Florida!
Party in the Park is a FREE event for the community to celebrate America’s birthday. The SPECTACULAR fireworks display is over Lake Apopka and preshow entertainment includes live music, family activities, and more for all ages.
Festivities begin at 6:00 pm. and the Fireworks Show starts at 9:15 pm.
Bring a chair or blanket and pack a picnic (no alcohol is permitted) for a fun night under the stars and colorful sky.
FESTIVITIES
Live Music by Ranahan/Fireworks Show/Games/Crafts/Food & Merchandise Vendors and More!
LIVE MUSIC
Ranahan will perform live as part of the preshow activities. The popular band performs country and Caribbean style party music.
FIREWORKS DISPLAY
The sky will burst with colors at 9:15 pm as the amazing display of fireworks lights up the night sky with breathtaking reflections on Lake Apopka.
PARKING
Parking is available at several locations on North Dillard Street.
No personal fireworks or alcohol are permitted.

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.

August

September

October

WINTER GARDEN HALLOWEEN EXPERIENCE:
Historic Downtown Winter Garden
Where: Historic Downtown Winter Garden on Plant Street
When: October 2025 PENDING...
Halloween is celebrated for 14 days in Winter Garden! Hosted by the City of Winter Garden, the annual Halloween Experience (October 18 - 31) provides FREE, fun, 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 at the Winter Garden Heritage Museum; a Halloween Celebration at the fall-themed Farmers Market, and more!
Click here for more information...

November

Health & Harvest Festival at the Winter Garden Farmers Market
When: Saturday, 2025 PENDING...
Time: 8:00 am – 1:00 pm
Where: Downtown Pavilion, 104 S. Lakeview Avenue & throughout the Farmers Market

Come out to the Winter Garden Farmers Market for the FREE Health & Harvest Festival on Saturday, November 2, to stay on top of your health while enjoying the market’s fall offerings.
•Event includes children and fitness activities, games, giveaways, cooking and gardening fun, health screenings, and more!
•All Health & Harvest Festival activities are complimentary.
•Festival activities and vendors will be located within the Winter Garden Farmers Market.
•The Health & Harvest Festival is co-hosted annually by Healthy West Orange and the City of Winter Garden.

Craft Affair 2025
When: Saturday, PENDING...
Time: 10:00am–2:00pm
Where:Jessie Brock Community Center
310 N. Dillard Street, Winter Garden

Arts & crafts lovers will enjoy shopping for one-of-a-kind items at the annual Craft Affair hosted by the City of Winter Garden Parks & Recreation Department. It is a great opportunity to shop for holiday and unique gift items!
All arts and crafts vendors are age 50+ creative friends, but every one of all ages is invited to shop the fair
If you are interested in being a craft vendor at this event and you are 50+, please complete a Special Event Vendor Policies & Application and submit to the Recreation Administrative Office, 310 N. Dillard Street, via fax 407-656-6504, or via email to recinfo@wintergarden-fl.gov. Questions, call Parks & Recreation at 407-656-4155.
Free to attend!

Small Business Saturday Sidewalk Sale
Saturday, November, 2025 PENDING...
All Day
Historic Downtown Winter Garden

Kick off the holiday shopping season at the annual Downtown Winter Garden Small Business Saturday Sidewalk Sale on the Saturday after Thanksgiving (November 30). 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. Live entertainment will add to the celebration!
The variety of downtown shops feature apparel, accessories, jewelry, home décor and greenery, cycling/running/sporting equipment, gourmet foods, health and beauty products, pet supplies, furniture, party-hosting supplies, seasonal merchandise, and much more.
When needing a shopping break, the variety of restaurants, coffee houses, bakeries, ice cream parlors, and chocolate shops provide the perfect pick-me-up. Take a seat at the expanded outdoor dining patios throughout downtown amidst the festive charm.
The Downtown Small Business Saturday Sidewalk Sale will be held rain or shine.
Sales, special offers, and operating hours vary per merchant.

Click here for more information...

December

Tis the Season Event Schedule 2024
Tis the Season for Making Merry Memories!
There's something magical in the air in downtown Winter Garden. You can just sense it as the sights and sounds of the season complement the small town charm of historic downtown. An abundance of festive decorations and light displays, including twinkle lit arches along the West Orange Trail in downtown's center, and carefully staged photo stations provide the perfect setting to create precious holiday memories. There are holiday tunes to hum along to as you stroll, courtesy of the centralized sound system. Colorful bursts of water playfully spurt from the Downtown Interactive Fountain. On select dates (see Holiday Happenings Daily Event Schedule below), there are complimentary live music performances, projection light shows, street performers, and more that add to the festive Normal Rockwell-like ambiance of downtown.

Click Here for all Holiday Happenings!

Light Up Winter Garden 2024
When: PENDING...
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 holiday entertainment, children's activities, and lots of holiday fun! Sponsored by Duke Energy and the City of Winter Garden.

More Info...

Winter Garden Christmas Parade
When: PENDING...
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!

More Info...

Holiday Market at Downtown
When: PENDING...
Time: 1:00-4:00pm
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.

More Info...

Winter Garden Christmas Golf Cart Parade
When: PENDING...
Time: 6:00pm
The 11th Annual Christmas Golf Cart Parade is an amazing sight of festive elaborately decorated golf carts making their way through historic downtown to spread holiday cheer. The parade loops around West Plant, entering east bound from Park Avenue and looping westbound on Woodland Street. Spectators should stake their favorite viewing spot along West Plant Street and bring a chair for comfort.
More Info...

De-light-Ful Decorations Contest 2024
Judging: PENDING...
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 2024
"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:
PENDING...

Watch video from Santa Run 2014...

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Dr. Martin Luther King, Jr. Community Celebration
Parade, Live Concert & Children's Activities
When: Monday, Jan. 20, 2025
Time: 11:00am - 4:00pm
Where: Downtown Pavilion, 104 S. Lakeview Avenue

Winter Garden Music Festival
Saturday, Feb. 22, 2025
11:00am - 10:00pm
Downtown Winter Garden on Plant Street
FREE/Rain or Shine!

Memorial Day
Monday, May 27, 2024

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

July 4: 9:15pm Fireworks at Newton Park

2025 Pending...

Click Here for all
Holiday Events

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

Downtown Winter Garden beginning at S. Dillard & Plant Street, Date Pending... 2024 at 10:00am. Parade continues to Historic Downtown Winter Garden on Plant Street.