Winter Garden Heritage & Music Festival

Celebrating the City’s 120th Anniversary

Established in 1903, the City of Winter Garden commemorates its heritage with a special 120th anniversary extravaganza. Festivities include six stages of entertainment, strolling performers, and much more! 

This Winter Garden Heritage & Music Festival is a FREE event for all ages and is brought to you by the City of Winter Garden along with the Winter Garden Heritage Foundation and other generous partners.

Live Music & Entertainment, 11:00 am – 10:00 pm

Simultaneous and continuous performances will be held at various outdoor stages throughout historic downtown stretching from Central Avenue to Dillard Street. The entertainment kicks off at 11:00 am and continues nonstop through 10:00 pm. 

Live Music & Entertainment Schedule

There will be 30 live music actof a variety of genres across six stages plus strolling performers! The performances are continuous and simultaneous from 11:00 am – 10:00 pm throughout Historic Downtown Winter Garden.

Click link to download music schedule of entertainers and venuesHeritage Music – Stage Schedule 2023.

A few of the many high caliber performances include Selwyn Birchwood, L & G Live Duo, Flight Scene, Big Ron Betts, and Michael Andrew & Swingerhead.

Please note that schedule is subject to change.

11:00 am – 1:00 pm

Paul Q-pek & Jeremy Birdsall (Rock)

City Hall Stage

Flight Scene (A Cappella Group-County, Top Hits)

Lakeview Stage

Garden Music School (Various Music)

Main Street Stage

1:00 – 2:00 pm

Freightliners (Blue Grass)

Loop Stage

Dominic Gaudious (Worldly Original Music, Australian Didgeridoo, Drums/Guitar/Vocals)

Centennial Plaza Gazebo

2:00 – 3:00 pm

L & G Live Duo (Pop, Soft Rock, 90s Hits)

City Hall Stage

Hayfire (Country)

Lakeview Stage

Brown Bag Bass Band (Brass Band & Funk)

Main Street Stage

3:00 – 4:00 pm

Shamanic Rootz (Reggae)

Loop Stage

The Absent Trio (Pop, Soft Rock, 90s Hits)

Centennial Plaza Gazebo

Amanda Breivogel & Steve Peshek (Acoustic Duo)

Butterfly Sculpture Garden

4:00 – 5:00 pm

Twojay Duo (R & B Jazz & Soul)

City Hall Stage

Annika Chambers & Paul Deslauries (Blues & Soul)

Lakeview Stage

Bryce Mauldin (Country)

Main Street Stage

5:00 – 6:00 pm

Selwyn Birchwood (Blues Band)

Loop Stage

Blewayle Duo (Classics, Top 40)

Centennial Plaza Gazebo

Chris Scalco Duo (Top 40, R & B)

Butterfly Sculpture Garden

5:00 – 7:00 pm

We Flip Entertainment (Variety Show)

Main Street Stage

6:00 – 7:30 pm

 Marlow Rosado & Orchestra (Salsa & Latin)

Lakeview Stage

6:00 pm – 8:00 pm

We Flip Entertainment (Breakdancers)

City Hall Stage

7:00 – 8:00 pm

Spazmatics (80s Hits)

Main Street Stage

8:00 – 9:00 pm

 Big Ron Betts (Blues, R & B, Funk, Soul)

Centennial Plaza Gazebo

John Beck (Rock & Caribbean, Music Steel Drums)

Butterfly Sculpture Garden

8:00 – 9:30 pm

Foreigners Journey (Rock & Roll)

Loop Stage

9:00 – 10:00 pm

Jose of Phenom Duo (Sax Soloist)

City Hall Stage

We Flip Entertainment (LED Jump Ropers)

Lakeview Stage

Michael Andrew & Swingerhead (Jazz)

Main Street Stage


Butterfly Sculpture Garden, 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

Strolling Performers Schedule

2:00 – 5:00 pm

Strolling Jugglers

We Flip Entertainment

4:00 – 8:00 pm

Austin Daniels

Strolling Guitarist

6:00 – 9:00 pm

Strolling Power Skippers

We Flip Entertainment

Kids’ Zone & Back to the Future Entertainment, courtesy of First Baptist Church of Winter Garden

As part of the Festival, the First Baptist Church of Winter Garden (125 E. Plant Street) is celebrating its 135th anniversary and the 100th anniversary of its Old Sanctuary building with a “Back to the Future” nostalgic stage show with Doc, Marty McFly, and a DeLorean. In addition, there will be live music and special guest Blippi, a popular children’s entertainer and educator. 

Kids’ Zone

Visit the large kids’ zone area and hop on board the children’s train. 

Vintage Cars Display

In addition, fifteen 1920 vintage cars will be on display and there will be tours of the Old Sanctuary as well as historical displays.

Food Vendors

Hot dogs, popcorn, cakes, and pretzels will be available at roll back prices.

History Walking Tours

Listed on the National Register of Historic Places, a great way to learn about the history of downtown’s buildings, monuments, and even its trees is by taking a walking tour. 

Guided History Walking Tour

The Winter Garden Heritage Foundation will host History Walking Tours of downtown at 11:00 am, 12:00 pm, and 1:00 pm during the Festival. The tour will go along Plant Street from Woodland Avenue to Lakeview Avenue.

The tour meeting location is at the Winter Garden Heritage Foundation Visitors’ Center, 21 E. Plant Street. No advance registration required.

Self-Guided Heritage Trees Walking Tour

self-guided Winter Garden Heritage Trees Walking Tour through historic downtown is available by following the map available here or a paper copy at City Hall and at the Winter Garden Heritage Visitors’ Center. The two-mile tour highlights 56 trees, many of which have labels with QR codes highlighting historic information. This tour is presented by the Bloom & Grow Garden Society.

Special Historical Exhibitions & Presentations

Downtown’s museums and art gallery have exhibitions, artifacts, and memorabilia depicting Winter Garden and West Orange County’s history. Admission is always FREE.

Below are the special exhibitions and presentations taking place during the Festival:

Outdoor Heritage Exhibit, Downtown Historic District 

The Downtown Historic District’s Architectural Beginnings

Historical architectural images from the archives of the Winter Garden Heritage Foundation will be displayed along Plant Street and Main Street. The displays will showcase former images of select historical buildings.

11:00 am – 6:00 pm

Winter Garden Heritage Museum, 1 N. Main Street

School Bells are Ringing: A History of Lakeview and Drew High Schools

With artifacts and photographs dating back almost a century, the exhibit features the history of Lakeview and Drew High Schools. Established in 1927, Lakeview High School did not admit African American students until 1969 when desegregation changed the educational system in Orange County. Charles R. Drew High School rose on Winter Garden’s east side in the 1950s, ensuring that black students received an education without having to travel to Orlando. 

The exhibit features the history of both schools from their inception to the day when all students in Winter Garden could attend classes together. 

10:00 am – 5:00 pm

Heller Hall at Winter Garden Heritage Research & Visitors’ Center, 21 E. Plant Street

Farming & Citrus Culture

Historic farm equipment through the ages will be on display.

11:00 am – 5:00 pm

Art in Public Places Gallery in City Hall, 300 W. Plant Street

Reflection of Time: Tribute to Local African American Artists.

The exhibition explores the journey of African American artists from the Winter Garden community and surrounding areas. This collective body of work preserves a small portion of the continuous American struggle, which is an African American struggle that needs to be told so that the importance can be felt year-round. 

The exhibition showcases artwork by local artists of different artistic disciplines, unified under one brushstroke that shares one common denominator—Black excellence. Patrick Noze, Crealdé School of Art Senior Curator of Exhibitions, curated the exhibit.

9:00 am – 10:00 pm

Central Florida Railroad Museum, 101 S. Boyd Street

Housed in a former train depot, the museum features an abundance of railroad artifacts and memorabilia, in addition to a working model train set.

Railroads of Winter Garden Presentation

1:00 pm and 2:00 pm

The presentation will provide highlights of the history of railroads that served Winter Garden.

Extended Museum Hours for the Festival, 9:00 am – 5:00 pm

SOBO Art Gallery, 127 S. Boyd Street

The SOBO Art Gallery is housed in a former fire station, a historical landmark, and is home to  the Winter Garden Art Association.

History Preserved: New Images of Winter Garden’s Architectural Legacy

Photographs highlighting many of the local architectural treasures documented in a 2021 survey of Winter Garden’s commercial and residential historic districts. The photographs are from the archives of the Winter Garden Heritage Foundation.

Arts in Motion

This exhibit of 2D and 3D artwork celebrates movement and motion form sports and exercise to concept like energy, fluidity, and mechanics. 

10:00 am – 4:00 pm

Rock of Ages – Live Musical at the Garden Theatre

It is only fitting that the historic Garden Theatre live production pays tribute to music during the Winter Garden Heritage & Music Festival. ROCK OF AGES  is a big, energetic tribute to the classic rock of the ‘80s, featuring all of your favorite rock anthems and power ballads, including: “We’re Not Going to Take It,” “Waiting for a Girl Like You,” “The Final Countdown,” “Every Rose Has Its Thorn,” and “Don’t Stop Believin’.”

The live show takes you back to the time of big bands with big egos playing big guitar solos, and sporting even bigger hair! This five-time Tony Award-nominated Broadway musical features the hits of bands Night Ranger, REO Speedwagon, Pat Benatar, Twisted Sister, and more.

Two performances will be held during the Festival at 2:00 pm and 7:30 pm. Click here to purchase tickets.

The Garden Theatre is a historical site. Originally built in 1935 as a single-screen cinema, the Theatre was the first in Central Florida built for “talkies!”

 Rock of Ages Book by Chris D’Arienzo, Arrangements and Orchestrations by Ethan Popp

Winter Garden Farmers Market – 120th Anniversary Tote Bag Giveaway (limited supply)

In celebration of the Winter Garden Heritage & Music Festival, the Winter Garden Farmers Market will be handing out complimentary 120th Anniversary commemorate reusable tote bags to the first 120 market goers that stop by the Information Tent at the Pavilion entrance. 

In addition, the Market is hosting a Valentine’s Day Celebration on the same day as the Festival with complimentary Valentine craft making at the KidZone tent at the Parking Garage Plaza (9:00 am – 12:00 pm), as well as live music and family friendly games on the lawn adjacent to the Pavilion.

8:00 am – 1:00 pm (tote bags distribution limited to while supplies last)

Downtown Pavilion, 104 S. Lakeview Avenue