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The 1928 Winter Garden Strawberry Festival

  • Nov 9, 2025
  • 2 min read


Everyone loves a fair. It could be a country event staged in a muddy field or a world-class extravaganza running for months in the heart of a big city, but fairs of all kinds always draw throngs of visitors to their attractions. The first fair I remember attending was the 1964-65 New York World's Fair. We attended five times, and I never forget that my grandmother loved the Mormon Temple Pavilion because she could sit in a comfortable chair in an air-conditioned room and watch a very soothing movie about the Latter-day Saints; sometimes she would nap. She also loved seeing Michelangelo's Pieta, on display at the Vatican Pavilion: "That marble came from my area in Italy." The Clairol Color Carousel (ladies only, please!) predated TikTok by allowing participants to visualize how they would look in various shades of hair- and would then provide each woman with the formula!


Here, our fairs most often centered around our agricultural production. In 1928, Winter Garden held its first Strawberry Festival, produced by our Hugh T. Gregory American Legion Post and the Winter Garden Chamber of Commerce. Local growers were planting strawberries during the prosperous 1920s, notably Ocoee's Hartle M. Bowness and Morgan C. Britt in Winter Garden. In his third year of production, Britt had 75 acres of strawberries under cultivation and area leaders decided it was time to celebrate the ruddy fruit.




A ticket to the First Annual Strawberry Festival Old Fashioned Ball, mailed to Mrs. Cohen Bray. Note the address simply reads "City."









An item from a century-old scrapbook in our Archive states that the festival was almost

rained out.




Resident Charlie Connell in the late 1990s remembered that "they would grease some pigs, they'd shave the pigs and grease them real good. And then you'd have to be on skates and catch those pigs and put them in a barrel to win. Well, there was a lot of almost winners. But anyway we had fun..."


A follow-up in the Winter Garden Journal of April 26, 1928 reported that "Mrs. Cohen Bray was given the prize as the most graceful dancer in the Virginia reel." (That's the dance Scarlett O'Hara and Rhett Butler scandalously performed in Gone with the Wind.)


Though strawberries grew well here, mostly in Tildenville and Ocoee, pioneer resident and retail grocer William F. Cappleman, Sr. said in 1970 that "it grew increasingly difficult to market the strawberries in Northern areas in an edible condition, since refrigeration was a some-time thing in that early era." Growers concentrated on profitable citrus and vegetable truck farming and, after one more Winter Garden festival was held, the celebration moved south to Plant City.




 
 

Healthy West Orange Heritage and Cultural Center

21 East Plant Street
Winter Garden, FL 34787

407-656-3244

 

Tuesday: 11am – 3pm

Wednesday: 11am – 3pm

Thursday: 11am – 3pm

Friday: 11am – 3pm

Saturday: 11am – 3pm

Central Florida

Railroad Museum 

101 South Boyd Street
Winter Garden, FL 34787

407-656-0559

 

Tuesday: 11am – 3pm

Wednesday: 11am – 3pm

Thursday: 11am – 3pm

Friday: 11am – 3pm

Saturday: 10am – 3pm

Website: https://www.cfrhs.org/

Heritage Museum

One North Main Street
Winter Garden, FL 34787

407-656-3244

 

Tuesday: 11am – 3pm

Wednesday: 11am – 3pm

Thursday: 11am – 3pm

Friday: 11am – 3pm

Saturday: 11am – 3pm

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FOUNDATION BOARD MEMBERS

Frank Chase, President

Mike Forrester, Vice President

Phil Cross, Secretary

Larry Cappleman, Treasurer

Ward Britt

Howard Brown

A.J. Burnett

Tom Burnett

Amanda Daluga

 

Stina D'uva

Cyndi Gustafson

Iliana Jones

Amy Quesinberry

FOUNDATION STAFF

 

Kristi Karst Gomen, Executive Director

kkgomen@wghf.org

Jeanne Griffith, Grant Writer
jgriffith@wghf.org

Will McCoy, Museum Director

wmccoy@wghf.org

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