Winter Garden Music Festival 2026
Saturday, February 21
11:00 am – 10:00 pm
Historic Downtown Winter Garden
Free Admission

MUSIC SCHEDULE FLYER 

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.

                                * 30+ Music Acts * 7 Stages (6 outdoor / 1 indoor)

   * Variety of Music Genres       * Onsite Beer & Wine Vendors

      * Pedestrian-Only/Streets Closed

       * Outdoor Dining at Downtown Restaurants (book reservations early) 

* Downtown Eateries & Shops plus Historic Charm

Remember to BRING A CHAIR to enjoy the music in comfort at the various stages. 

NO PERSONAL COOLERS AND NO OUTSIDE ALCOHOLIC BEVERAGES ARE PERMITTED.

Rain or Shine -- the Winter Garden Music Festival will take place on February 21.

Stage Locations:

Butterfly Sculpture Park, 240 W. Plant Street
Centennial Plaza Gazebo, 101 W. Plant Street
City Hall Stage, 300 W. Plant Street
Garden Theatre on Plant, 160 W. Plant Street (indoor)
Lakeview Stage, 104 S. Lakeview Avenue
Loop Stage, 427 W. Plant Street
Main Street Stage, 1 N. Main Street

Music Schedule:

11:00 am – 12:00 pm

Dublin Beat
Irish Folk Band
Loop Stage

Tonic Duo
Soul, ElectroPop
Butterfly Sculpture Park

The Porchdogs
Cajun & Zydeco
Centennial Plaza Gazebo

12:00 pm – 1:00 pm

The Boots
Top 40s, Rock, Funk, & Pop
City Hall Stage

Oklahoma Stackhouse
Southern Tropical Rock
Lakeview Stage

Vocal Flash
Pop Acapella
Main Street Stage

1:00 pm – 2:00 pm

About Tuesday
Pop-Punk/Rock Band
Loop Stage

Gilly and the Girl
Contemporary Acoustic
Butterfly Sculpture Park

Sandy Back Porch
Bluegrass
Centennial Plaza Gazebo

2:00 pm – 3:00 pm

Paul Q-Pek Duo
Pop/Rock, 70s & 80s
City Hall Stage

Billy Buchanan & His Rock ‘n Soul Revue
Soul, Funk, & Blues
Lakeview Stage

SouthBound
Country
Main Street Stage

3:00 pm – 4:00 pm

Flatt Out Blue with Caleigh Barnett
Bluegrass
Loop Stage

Allie and the Absent Trio
Acoustic Folk/Pop
Butterfly Sculpture Park

Rumba Brothers
Latin-Jazz & Flamenco Fusion
Centennial Plaza Gazebo

4:00 pm – 5:00 pm

Live Hart Trio 
Indie, Soul
City Hall Stage

The Hooligans
British
Lakeview Stage

Phoenix 5 and the Rising Horns
Funk, Soul, Reggae
Main Street Stage

5:00 PM - 6:00 PM

Tom Jackson Band
Country
Loop Stage

Red Mint Duo
Soft Rock & Pop
Butterfly Sculpture Park

CYN
R & B
Centennial Plaza Gazebo

Moonflower: The Spirit of Santana
Tribute Band to Santana
Garden Theatre on Plant 

6:00 pm – 7:00 pm

Big Ron Betts Trio
Blues
City Hall Stage

Spazmatics
'80s Pop & Rock
Lakeview Stage

O-Town Motown
Motown
Main Street Stage

7:00 pm – 8:00 pm

Selwyn Birchwood
Blues
Loop Stage

Jeremy’s Jazz Trio
Jazz
Butterfly Sculpture Park

Winter Garden Music School
Various Genres
Centennial Plaza Gazebo

Moonflower: The Spirit of Santana
Tribute Band to Santana
Garden Theatre on Plant

8:00 pm – 9:00 pm

Julie Black & Her Band
Mix of Blues, Jazz, & Soul
City Hall Stage

8:00 - 9:30 PM

Latin Ambition
Energetic Latin
Main Street Stage

8:30 pm – 10:00 pm

The Boy Band Project
Boy Bands Tribute
Lakeview Stage

9:00 pm – 10:00 pm

Shot of Poison Tribute Band
Hard Rock, Glam Metal
Loop Stage

Breakdancing Show Schedule

Location: W. Plant Street and N. Woodland Street 

A high energy show composed of the well-known street dance, breakdancing. The dancers not only bring the traditional street dance with funky rhythms, but also extreme acrobatic moves. Watch as these b-boys and b-girls take you through a warmup, funky dances, crazy solos, an audience compelling dance battle, and an over-the-top ending! From the time this dance was invented in the 70s until now…it has never disappointed!

• 5:00 PM
• 5:30 PM
• 7:00 PM
• 7:30 PM
• 9:30 PM

PARKING & SHUTTLE INFORMATION - Free!

Public Parking Facilities Walkable to Event (no shuttles):

• Downtown Parking Garage (three levels), 160 S. Boyd St
• Boyd Street 117-space parking lot, 37 N. Boyd St.
• Winter Garden City Hall, 300 W. Plant St.
• Sam Williams Little League Complex, 415 S. Park Ave.
• Veterans Memorial Park, 420 S. Park Ave.
• S. Woodland St. & E. Joiner St. (2 parking lots on either side of S. Woodland St.)
• Behind Winter Garden Post Office (off N. Lakeview Ave. between W. Plant St. and W. Newell St.)
• Parking Lot at W. Bay St. and N. Highland Ave.

Please Note: Parking along West Plant Street from Dillard Street to Park Avenue, and a portion of the adjoining side streets, will not be available for parking due to the road closures.

Shuttle Service, 10:00 am - 11:00 pm

Courtesy of the City of Winter Garden, a COMPLIMENTARY Shuttle Service will operate continuously from 10:00 am to 11:00 pm.

SHUTTLE STOPS:

*Dillard Elementary School, 311 N. Dillard Street (offsite parking)

*848 E. Plant St. Parking Lot (southeast corner of 9th St. and East Plant Street / across from Winter Garden Library) (offsite parking)

*Corner of Dillard Street and Plant Street (event shuttle stop)

ARRIVAL:

Shuttle will pick up from Dillard Elementary School parking lot and Parking Lot at 848 E. Plant Street (southeast corner of 9th Avenue / East Plant Street (848 E. Plant St. and drop-off to the Downtown Event Shuttle Stop (corner of Dillard Street & Plant Street). 

RETURN:

Catch the Shuttle from the Downtown Event Shuttle Stop (corner of Dillard Street & Plant Street) to return to the Dillard Elementary School parking lot or Parking Lot at 848 E. Plant St. (southeast corner of 9th Street / East Plant Street).

Event SPONSORS

Thank you to our 2026 Winter Garden Music Festival sponsors for their generosity and participation to make this event possible for the community!

Winter Garden Farmers Market, 8:00 am - 1:00 pm

The Winter Garden Farmers Market will operate as usual the morning of the Music Festival. Just steps away from the Festival, stop by the Market (8:00 am - 1:00 pm)  while attending the Music Festival. You will find several of the Market vendors set up along the Festival instead in their usual spots providing your favorites throughout the length of the Festival.

Downtown Pavilion, 104 S. Lakeview Avenue, 8:00 am - 1:00 pm

Road Closures (Saturday, Feb. 21, at 2:00 AM - Sunday, Feb. 22, at 2:00 AM)

West Plant Street from Dillard Street to Park Avenue, as well as a portion of adjoining side streets, will be CLOSED for this event from Saturday, February 21, at 2:00 am through Sunday, February 22, at 2:00 am. Additional road closures on S. Boyd St., N. Lakeview Ave, and S. Woodland St. are expected starting Friday, at 8:00 am to set up stages. The road closures will allow downtown to turn into one mega outdoor concert venue!

Veterans Memorial Park - DELAYED OPENING at 10:00 AM (Feb. 21)

Please note that the gates of Veterans Memorial Park, 420 S. Park Avenue, will not open until 10:00 am on February 21. There will be no access to pickleball / tennis / basketball courts and all park facilities until the gates open at 10:00 am. Veterans Memorial Park is an offsite parking location with parking attendants for the Winter Garden Music Festival.

Please Note: The use of drones is prohibited at City events .

WARNING of Fraudulent Online Solicitation: If you receive correspondence by either a third-party company or the likeness of the City of Winter Garden via email or social media about vending at a City event, it is fraudulent solicitation and do NOT engage in providing information or any form of payment.