Herman Wilkinson Jr.

  On August 16, 1953, in Boston, Massachusetts, Herman Wilkinson, Jr. made his grand entrance into the world as the beloved son of Herman Wilkinson Sr. and Margie L. (Hill) Wilkinson.  Herman’s life was filled with travel, family, and the kind of presence that lingered long after he left a room.  Summers in Alabama and Iowa gave him 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 a band of brothers, and a mentor, Dr. Donald Brown, who became a lifelong influence.  The following year while working a summer job at Boyden Gym Pool at UMass, Herman met 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.  They gathered a circle of friends so large it blurred the lines between family and community.  There, they welcomed their son, Don in 1973.  Later, they joined Wesley United Methodist Church in 1980 and married in 1981 at the Stanley Park Rose Garden in Westfield, MA.  It was a wedding overflowing with love, as over 300 guests came together to celebrate.  They honeymooned on Long Island, New York and in 1984, they welcomed their daughter Kira, 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.  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.

  Faith was the foundation of his life.  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 The 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, and he prayed on his knees until he physically could not.  He celebrated his 72nd birthday in grand style just two days before departing peacefully while 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’s just Herman shining through.

Visitations are 5-7 p.m. Thursday, September 11, 2025, and 10-11 a.m. Friday September 12, both at Wesley United Methodist Church, 741 State Street, Springfield, MA.  Funeral services will follow at 11 a.m. Friday, Sept. 12, at the church.

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