30+ Acts Headline 2025 Winter Garden Music Festival

January 15, 2025

A look-forward-to event located in the heart of Downtown Winter Garden that is like no other! The City of Winter Garden presents their annual Winter Garden Music Festival, a FREE multi-stage, mega outdoor concert featuring a variety of talented, toe-tapping live entertainment and music genres. This 11-hour event includes continuous and simultaneous musical performances throughout beautiful, historic downtown Winter Garden. Truly a can’t miss event scheduled on Saturday, February 22, 11 a.m. to 10 p.m.

More than 30 talented, top-notch artists headline this year’s music extravaganza, representing a broad range of musical tastes. Genres include country, rock, contemporary, folk, flamenco, mariachi, blues, salsa, jazz, pop, reggae, and more. Check the music schedule below to catch your favorite band or music preference or discover a new favorite. Stroll through the pedestrian-only streets (downtown roads closed for the event) and bounce around all six stages a walkable distance apart.

Onsite vendors will offer a selection of refreshments including beer and wine for sale. Sip and stroll to the various acts throughout downtown, and take in the exciting atmosphere and music-filled air. Feel free to stand and watch the performances but bringing a lawn chair is greatly suggested. However, don’t sit for long as dancing is highly encouraged!

This event is family friendly with a complimentary kids’ zone for all ages from 11 a.m. to 4 p.m. at Winter Garden’s First Baptist Church, 125 E. Plant St. (Children must be accompanied by an adult as supervision is not provided.)

The small-town historical downtown creates the perfect backdrop for this event, making a perfect post- worthy opportunity to share with friends and family. In addition to the top talent performances, downtown offers a plethora of other fun activities including an interactive fountain for kids, Centennial Plaza with swings and benches, a pocket park, unique retail shops, as well as casual and fine dining, bakeries, coffee shops, and ice cream parlors. Sit at outdoor seating at one of the local eateries to continue enjoying the music and fuel up before heading to the next performance. Plan ahead by making reservations where applicable.

STAGE LOCATIONS:
Butterfly Sculpture Park, 240 W. Plant Street
Centennial Plaza Gazebo, 101 W. Plant Street
City Hall Stage, 300 W. Plant Street
Lakeview Stage, 104 S. Lakeview Avenue
Loop Stage, 427 W. Plant Street
Main Street Stage, 1 N. Main Street

Winter Garden Music Festival Schedule 2025

11:00 am – 12:00 pm

Remedy Tree
Blue Grass
Loop Stage

Pacific Rush Duo
Coastal Rock
Butterfly Sculpture Park

Porchdogs
Cajun & Zydeco
Centennial Plaza Gazebo

12:00 pm – 1:00 pm

Red Mint
Soft Rock & Pop
City Hall Stage

Vocal Flash
Pop Acapella
Lakeview Stage

Petty USA
Tom Petty Tribute Band
Main Street Stage

1:00 pm – 2:00 pm

Southbound Band
Country
Loop Stage

Jukebox Joes
Pop Vocal Harmony
Butterfly Sculpture Park

Rumba Brothers
Latin-Jazz & Flamenco Fusion
Centennial Plaza Gazebo

2:00 pm – 3:00 pm

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

Bobby Blackmon & The B3 Band
Contemporary Soul Blues
Lakeview Stage

About Tuesday
Pop-Punk/Rock Band
Main Street Stage

3:00 pm – 4:00 pm

Kat Riggins
Blues
Loop Stage

Amanda & Steve
Acoustic Covers
Butterfly Sculpture Park

Operazzi
Opera Hits
Centennial Plaza Gazebo

4:00 pm – 5:00 pm

Tones & Tunes Dueling
Variety of Genres
City Hall Stage

The Hooligans
British
Lakeview Stage

Bryce Mauldin
Country
Main Street Stage

5:00 pm – 6:00 pm

Tom Jackson Band
Country
Loop Stage

TwoJay Duo
R&B, Soul
Butterfly Sculpture Park

Charlie Pace
Multi-Genre Acoustic Vocals
Centennial Plaza Gazebo

6:00 pm – 7:00 pm

Walker Mathison & The Ranahan Band
Country & Mega Hits
City Hall Stage

Spazmatics
80’s Pop & Rock
Lakeview Stage

O-Town Motown
Motown
Main Street Stage

7:00 pm – 8:00 pm

Violectric
Instrumental Top Hits
Loop Stage

Brian + Hannah
Pop, Jazz, Soft Rock
Butterfly Sculpture Park

Craig Thompson Project
Reggae, Top 40’s Hits, Soul & More
Centennial Plaza Gazebo

8:00 pm – 9:00 pm

Big Ron Betts Trio
Blues
City Hall Stage

8:00 pm – 10:00 pm

Sam Lowe & Whey Jennings
Country
Lakeview Stage

Stella Beat
Energetic Latin
Main Street Stage

9:00 pm – 10:00 pm

Foreigners Journey
Rock & Roll
Loop Stage

Vocalitas
Modern Jazz & Swing
Butterfly Sculpture Park

Parking is always free in downtown Winter Garden. Complimentary shuttle service will be provided for the event. For details, visit the City of Winter Garden website.