KEY WEST’S HOMECOMING TRADITIONS TURN 75

a group of women standing next to each other
The 2025 Key West High School Homecoming court includes, from left, Tamika Kelly, Whitney Nervilus, Emmy Jackson, Gianna Felini, Chloe Blackwell and Janelle Rodriquez.

Seventy-five years have passed. The country has elected a dozen or so presidents. Wars have been fought, won, lost and debated. Music has moved from sock hops to hip hop. The differences are vast between the world of 1950 and that of today’s high school students in 2025. 

TV was in black and white. Segregated schools were only black or white. Baby Boomers were still actual babies. Yes, high school students of 1950 and 2025 are separated by 75 years of culture and technology, and yet united by an island that still treasures its hometown traditions. 

One of those traditions continues this week, when Key West High School’s football team takes the field Friday evening for the school’s 75th annual Homecoming game, halftime of which will see the crowning of the 75th Homecoming queen, voted into the crown by her fellow students.

Deanna Archer wore the school’s very first crown in 1950. It was made of cardboard, Archer recalled in 2000 when I interviewed her for the 50th anniversary of her coronation. 

Archer’s age and health no longer permit her to participate in this year’s traditions, but one of the first queen’s early successors led the Oct. 13 Homecoming parade up Flagler Avenue, from the high school to the football stadium on Kennedy Drive. The stadium was brand new in 1950 — and just recently renewed for 2025. 

Judy Henriquez, the ’57 queen, led the parade as grand marshal. After she graduated with her fellow Conchs, she would go on to marry the man who would lead Monroe County schools for decades, the late superintendent Bookie Henriquez, who died earlier this year on Valentine’s Day.

The parade kicked off a week of tradition and celebrations that will be capped off by the Friday, Oct. 17 football game that will see the queen crowned at halftime, followed by the Homecoming dance at the high school on Saturday, Oct. 18. All former Homecoming queens are invited to be introduced at the football game. Please arrive at 6 p.m. to line up.

a group of people riding on the back of a train
The Key West High School football team rides the Conch Tour Train in the Oct. 13 Homecoming parade. CONTRIBUTED
a woman is sitting in a golf cart
Judy Henriquez, 1957 queen, rides as grand marshal in the recent Homecoming parade. CONTRIBUTED
a red convertible car driving down a street
A member of the 2025 Homecoming court, Chloe Blackwell, escorted by Jake Ferguson, rides in the annual parade. CONTRIBUTED
Mandy Miles
Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.