The English High School Alumni Association ‘s All-Class Reunion on Saturday, October 10, 2026, at Florian Hall in Dorchester, Mass., continues the celebration of the remarkable 205-year legacy of America’s oldest public high school.
Founded in 1821, EHS has educated generations of students who have gone on to distinguish themselves in public service, business, education, the military, athletics, the arts, throughout Boston and across the nation.
The October 10 celebration will bring together alumni, current students, families, friends, and supporters to celebrate both the school’s proud history and its continuing impact on future generations.
A Tropical Extravaganza
The theme for the evening, a “Tropical Celebration,” will create a festive atmosphere for alumni to reconnect and celebrate their shared legacy. Guests will be encouraged to get into the spirit with tropical attire and activities, including: West Indian, Caribbean, and Hawaiian outfit contests; music and dancing; food, raffles, opportunities to reconnect with classmates and fellow alumni, and meet current students and teachers.
Special Tribute to the Tuskegee Airmen
A highlight of the evening will be a special presentation honoring two extraordinary alumni who share the historic legacy of the Tuskegee Airmen.
Additionally, a model of the legendary Tuskegee Airmen “Red Tail” aircraft will be presented to EHS in honor of Brigadier General Enoch “Woody” Woodhouse, English High School Class of 1944, who will celebrate his 100th birthday on January 14, 2027. The model will be a replica of an aircraft flown by fellow Tuskegee Airman Lieutenant Colonel Leo Gray, EHS Class of 1942.
The aircraft model was created and is being donated by Robert “Bob” Desourdis, a longtime champion of efforts to preserve the history of the legendary unit. Desourdis previously created a similar model for the Tuskegee Airmen Museum in Campomarino, Italy, near the historic Ramitelli Airfield, where members of the Tuskegee Airmen’s 332nd Fighter Group were stationed during World War II. Marco Altobello, who oversees the museum in Italy, may be on attendance.
Celebrating 205 Years of English High
“This is much more than a reunion,” said Greg Hayes, Alumni Board Chair and a member of the Class of 1967. “It’s an opportunity for generations of EHS alumni to come together, celebrate where we came from, honor those who made history, and introduce today’s students to the legacy they are carrying forward. ”The Alumni Association invites all graduating classes to participate and encourages alumni to reach out to former classmates, teammates, teachers, and friends and make the October 10 reunion a true celebratory gathering of the EHS family.
EVENT INFORMATION
• What: English High School Alumni Association All-Class Reunion — ‘Tropical Celebration’
• When: Saturday, October 10, 2026
• Where: Florian Hall, Dorchester, Massachusetts
• Special Presentations: Tuskegee Airmen “Red Tail” aircraft model honoring Brigadier General Enoch “Woody” Woodhouse, EHS Class of 1944, and commemorating Tuskegee Airman Lieutenant Colonel Leo Gray, EHS Class of 1942
• Hosted by: English High School Alumni Association
For additional information about the English High School Alumni Association and upcoming events, visit EnglishHighAlumni.org.
The English High School Alumni Association works to preserve and celebrate the history and traditions of The English High School of Boston while strengthening connections among alumni, supporting current students, and helping future generations understand the significance of being part of America’s oldest public high school.