A Woodstock Journey: Johnnie Singh ’56 on Seven Decades of Memories

28 Mar A Woodstock Journey: Johnnie Singh ’56 on Seven Decades of Memories

In this special interview, conducted by Grace, a student intern in the Alumni Office, Johnnie Singh ’56 reflects on his memories of Woodstock in the 1950s, his journey beyond the hillside, and the lessons that have shaped his life. His stories offer a glimpse into a bygone era of Woodstock while highlighting the timeless values that continue to define the school today.

By Grace, Class of 2026, Alumni Office Student Intern

Few people can say they’ve seen Woodstock evolve over nearly seven decades, and Johnnie Singh—Class of 1956—is one of them. When I recently had the privilege of interviewing him, it felt like stepping into a time machine. His journey is nothing short of extraordinary, and it all began with a simple decision: to attend Woodstock.

Growing up in Kolkata, Johnnie’s path to Woodstock was shaped by his family. His sister, Aisha, was already a student, and when it came time for him to choose between Woodstock and St. Paul’s in Darjeeling, he followed in her footsteps. From 5th grade onwards, Woodstock became his home for the next seven years, shaping him into the person he is today.

“Woodstock was always beautiful,” Johnnie reminisced. The school had a strong American presence—most students were children of missionaries or generals. The curriculum was American, and 90% of the students were from the U.S. or Europe. Unlike today, there were no laptops, no modern heating systems, and only American food in the cafeteria. Despite the differences, the heart of Woodstock remains unchanged. The friendships, the sense of adventure, and the life lessons still define the school experience.

Johnnie had a deep love for both softball and drama, spending much of his time on Hanson Field and in Parker Hall. While his family envisioned him joining the Air Force, he had other plans—ones that would take him far beyond what they expected. After Woodstock, he attended St. Xavier’s College in Kolkata before setting out on an unforgettable adventure: hitchhiking through Europe. From meeting kind strangers to forming lifelong friendships—like his friend Bruno in Italy—this journey shaped his worldview. “Bruno became my best friend for life,” he shared, though with a bittersweet note, as Bruno passed away a few years ago.

Johnnie eventually made his way to England, where fate played its part. He met his future wife Dianne’s mother, who encouraged him to stay. He became an accountant, and Dianne and Johnnie now own an accounting firm, DiJon & Co, in Poole, UK—proving that life often takes unexpected yet fulfilling turns.

When asked what Woodstock taught him, Johnnie’s answer was simple yet profound: self-reliance, honesty, sincerity, and the ability to tell the truth. These values, ingrained in him at Woodstock, guided him through every stage of life. His advice to students is, “Keep up with technology and follow your dreams. Have determination and dedication, and excel in it. Remember that Woodstock will always be your backbone.”