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Celebrating 240 Years of Excellence

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Titchfield High School Celebrates 240th Anniversary with “Mother of All Reunions” in Port Antonio, Jamaica .

Titchfield High School, the fifth oldest high school in Jamaica, proudly announces its 240th anniversary celebrations with a landmark reunion week dubbed the “Mother of All High School Reunions.”

The event runs from March 29 to April 6, 2026, and will showcase the enduring spirit of Titchfield’s alumni, families, and the Port Antonio and by extension...the Portland community.

The week-long festivities will unfold across multiple iconic locations in Port Antonio, a resort town renowned for its natural beauty. Alumni from Canada, the United States, Europe, and other regions are expected to converge for a celebration that honours history, friendship, and a shared commitment to education.

Activities will commence with a 5K Road Run organized by the Shelton Project Charity Group on Sunday, March 29 at dawn, followed by a high-energy Meet and Greet at 6:00 p.m. at the Errol Flynn Marina in the heart of Port Antonio. We honour the school’s great history with a March through the town on Monday morning March 30. Throughout the week, attendees will enjoy a series of workshops at the school on March 30 and 31, followed by a high energy sports day on the school grounds on Wednesday April 1.

The Wagglas Health Fair, a signature event produced by the Wagglas Group, will take place at the school on April 2, offering health screenings and wellness resources to the community.

On April 3, we venture out of town to the beautiful Swift River at Canewood Rd District, Hope Bay for a riverside cookout hosted by our very own Iyabinghi of Akwaaba Kitchen.

Our Gala Dinner and dance on Saturday April 4 will feature the Chief Justice of Jamaica and prominent past student, Brian Sykes, as keynote speaker and will also see the Governor-General, Sir Patrick Allen (Portlander) in attendance. The dinner will be followed by a Thanksgiving Church Service at Christ Church on Easter Sunday, April 5. A marquee highlight will be the Reunion Family Fun Day at the school on Easter Monday, April 6 to end a fabulous week of celebration.

Residents and visitors of Port Antonio will benefit from the influx of guests, with increased activity for local businesses, hospitality venues, transport services, crafts traders, and tour operators. Organizers emphasize this as a shared opportunity for economic and cultural exchange, while retaining a strong focus on academic legacy and community service.

“We are building something unforgettable,” said Anthony Nelson, a Titchfield alumnus and reunion committee member.

Michael Haughton, CEO of Wagglas Group, added, “This will be one for the ages. I’m looking forward to reconnecting with friends and colleagues.”