Mr. Herman Wilkinson, Jr.

On August 16, 1953, in the city of Boston, Massachusetts, Herman Wilkinson Jr. made his grand

entrance into the world, the beloved son of Herman Wilkinson Sr. and Margie L. Wilkinson

(Hill). Herman’s life was filled with travel, family, and a whole lot of personality—summers in

Alabama and Iowa gave him both southern warmth and midwestern grounding, while Boston

provided the backdrop for a life destined to touch many.

In 1968, Herman traded Boston for Amherst when he joined the A Better Chance program and

attended Amherst Regional High School. There he gained not only an education but also a band

of brothers and a mentor, Dr. Donald Brown, who became a lifelong influence. But the true plot

twist came in 1969 when a summer job at the Boyden Gym Pool at UMASS introduced him to a

young woman in a red bikini named Pearl. Herman never forgot that moment, and he never let

Pearl forget it either.

After graduating in 1971, Herman attended UMass Amherst, where he and Pearl continued their

love story and gathered a circle of friends so large it blurred the lines between family and

community. They welcomed their son Don in 1973, while students at UMass. They would join

Wesley United Methodist Church in 1980, and were married in 1981 at the Stanley Park Rose

Garden in Westfield, Mass. It was a wedding for the ages with over 300 guests. They

honeymooned on Long Island, New York, and in 1984 their daughter Kira arrived, completing

the family team.

Herman built a career marked by dedication to people and education: from Digital Corporation

(1980–1996), to Dean of Students at New Leadership High School, to Assistant Director of

Admissions at American International College where he retired after 10 years. He influenced,

mentored, and inspired countless students along the way, not just with guidance but with the

genuine care and thoughtful conversations that made people feel seen and valued.

His faith was the foundation of his life, and Wesley United Methodist Church became a second

home. Herman served faithfully as an adult Sunday school teacher, co-led the youth group with

passion and humor, and stood as a lay leader for many years. He also served on many church

boards, always offering wisdom and leadership. Among his greatest commitments was serving as

the chairperson of the Martin Luther King Jr. Memorial Scholarship Breakfast.

Beyond titles and jobs, Herman’s legacy was family. He was proud of building a life that showed

what was possible: marriage, children, education, home, faith, and the strength to overcome

obstacles with grace. He voted, he prayed, he provided, and he taught his children the value of

kindness, relationships and walking through life with integrity. His keys to life were simple yet

profound: treat others as you want to be treated, believe in God, pray, love, make someone smile,

and help others.

Herman had an ear for music, a heart for travel, and a laugh for comedy. But more than anything,

he loved family, near and far, older, and younger. He made sure everyone knew the stories and

history that bound them together. Family reunions were not just gatherings to him; they were a

way to keep the family’s love and legacy alive. His smile was as bright as his spirit—welcoming,

warm, and often paired with a story or joke that left you better than when you came. And who

could forget that signature walk—equal parts George Jefferson strut with Obama cool—that

announced his presence before he ever said a word.

In his final season, Herman remained the light he had always been. He opened his home to

family and friends for visits and conversations, prayed on his knees until he physically could not,

and celebrated his 72nd birthday in grand style just two days before departing peacefully at home

on August 18th. He left this world happy, grateful, and full of thanks to God.

Herman leaves to continue his legacy: his loving wife W. Pearl; son Don (Steph); daughter Kira

(Eric); grandchildren Aja, Alexandra, Kalyn, Kyrsten, Kia, Kyle, and Ellington; great-

grandchildren Adrian and Olivia; two sisters, Debi and Val; sisters-in-law Rose, Regina, and

Mary; brother-in-law Charles;(Francine) and a host of nieces, nephews, cousins, and friends.

When you think of Herman, remember his smile, his laughter, his light, his faith, his love for

God and family, and his commitment to legacy.

And if you catch yourself walking with a little extra swag, don’t worry. That is just Herman

shining through.

Services Entrusted to:

Harris~Wheless Memorial Funeral Home & Cremation Service 

Final Arrangements will be announced by 

Harrell Funeral Home Inc,

Springfield, MA 

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