- April 9, 2025
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Country-pop singer Jordan Mohr, of West Orange High, performs on the DME Artist Development Stage.
Artist Kirstie Hosp displays her work at an outdoor arts and crafts show, by the Masonic Lodge.
Hand made holiday decorations by artist Karen McGowan.
Yaretzi Miranda gets her face painted at the outdoor art show.
The Halloween hay maze at City Hall was less spooky and more smiles.
The Porch Dogs play some zydeco at the Plant Street gazebo.
Dogs of all shapes and sizes were out for a day of fun at the festival.
Lisa Habersbrunner’s dog, Ellie, was dressed for the weather.
Shawn Dennis' boxer, Thanos, doesn’t fear the weather.
Morrissey Blvd. plays the City Hall stage.
The Dublin Beat Irish Band take the Loop Stage, across from Plant Street Market.
Sofia Alpizar attempts an Irish step dance as the Dublin Beat Irish Band play their set.
Reese Miller navigates as her dad, Ethan, acts as shoulder chauffeur.
Cat Ridgeway & the Tourists play the Main Street Stage.
Carmen Jones gets her photo taken at the orange mural with We Flip Entertainment performers Johnny Tsunami and Narada.
The Tom Jackson Band bring their brand of county music to the Lakeview Stage.
Daniel Lombardi and Tom Jackson trade riffs on "Wagon Wheel."
Danielle Jackson, Mary King and Caryl Osteen dance a Texas two-step as the Tom Jackson Band plays their rendition of “Wagon Wheel.”
Lane Merkle is proud to wear his firefighter uniform; his dad, Brian, is fire lieutenant/paramedic with the Lake County Fire Department.
Aliyah Chu shares a cuddle with Shelton, a therapy horse from Soul Haven Ranch.
Soul Haven Ranch horses pull the carriages for all of downtown Winter Garden’s seasonal events.
Liza Marie Morales jams with Mike Walker at the DME Artist Development Stage.
Ocoee High students Olivia Brooks and Kaylee Mohabir spent the day volunteering at the festival.
Thomas Wynn and Hannah Harber play their rendition of The Band’s classic song “The Weight” at the Loop Stage.
The Gerry Williams Band play Boz Scaggs’ “Dirty Low Down” at the Lakeview Stage.
Street-side seating was hard to come by as the day went on.
Food trucks get all the attention in between band sets.
Melanie and Owen Herrera enjoy some curbside dining.
Mini donuts draw a big crowd.
The breakdancers of We Flip Entertainment show their skills at the City Hall Stage.
Bassist David Traver and drummer Matt Bloodwell, with 90’s cover band Anti Idol, play the Loop Stage.
Gabriella Mason solos as Orlando-based rock band Hello Sister takes the stage at Sam Williams Little League Complex.
Grace Mason, on bass, and Scarlett Mason, on drums, round out Hello Sister’s power trio.
Hello Sister invites Abby Anderson, and friend Olivia Fitzpatrick, onstage to celebrate Anderson’s 14th birthday.
Acoustic artist Molly Holton sings Amy Winehouse’s “Rehab.”
It’s a fall festival but Plant Street retailers are ready for Christmas.
Gamalier Reyes gets the crowd dancing with Salsa and Latin beats.
Tiana Ocasio and Enrique Nieves get into the groove.
Giselle Zavala and Aldo Roman try to stay warm as evening temperatures drop.
Sue Fattal and Souad Warid brace for a chilly night.
Chad Wolinski of The Spazmatics uses a megaphone to cover the vocals for The Buggles’ “Video Killed the Radio Star.”
Michael Andrew takes the Main Street Stage as the last act of the festival.
Michael Andrew and Swingerhead get a cheer with Frank Sinatra’s “I Get a Kick Out of You.”
Michael Andrew was the headline singer and bandleader at the Rainbow Room in New York City, and band leader and singer at Merv Griffin’s “Coconut Club.”
Downtown Winter Garden was filled with the sounds of celebration as the city marked its founding, 118 years ago, with the community-wide Winter Garden Fall Heritage & Music Festival on Saturday, November 6.
The free event, presented by the City of Winter Garden and the Winter Garden Heritage Foundation, featured a variety of entertainment for all ages including art exhibits, games, and live music by a range of performers; from homegrown bands to national acts.
Chilly weather and morning showers did not stop the party or dampen the spirit. Vendors, artists, and food trucks were out in force, while bands performed on outdoor stages throughout the downtown area..
