On September 6th, our family was shattered by the sudden and tragic death of Howard Kingsley, a beloved husband, father, grandfather, and a dedicated Army veteran. Howard was struck from behind by a motorist while riding his bicycle with the Pachyderm Pedalers, a cycling group he loved dearly. Tragically, he was just four miles away from completing a 30-mile charity ride when the driver, who had “looked down for one second,” failed to see him. In an instant, a man who had lived a life of service and love was taken from us, leaving a void that will never be filled.

This devastating loss came just one day after his wife Cheryl’s birthday. After 40 years of marriage, they had built a full life together rich in love, laughter, and partnership. Howard wasn’t just Cheryl’s husband; he was her best friend, her rock, and her constant support in every way.

Howard was well known in the cycling community for his bright yellow Army cycling jersey and matching yellow bike. He was a familiar and uplifting presence on the road—and was extremely strict about road safety, always following every rule and doing everything possible to protect himself and those around him. That makes the manner of his passing all the more painful.

At home, Howard was the primary provider, managing all the household expenses and ensuring Cheryl was free from financial worry.

This GoFundMe is for Cheryl, who now faces the heartbreaking task of moving forward without her life partner. Since Howard’s death, Cheryl has encountered one roadblock after another. Life insurance is not immediate—there are waiting periods, paperwork, and a mile-long checklist of legal and financial tasks she must now face alone. She was only granted three paid bereavement days, and received the devastating news of his death while at work. Understandably, she is not yet ready to return. The grief is still raw, and the future feels uncertain.

Cheryl is strong and independent, and asking for help is not something that comes easily to her. But right now, she needs support—not just emotionally, but financially, as she works through this painful and complex transition.

I’m writing this as Howard’s daughter-in-law. For nearly 13 years, he’s been a second father to me—kind, present, supportive, and always ready with a story or some gentle guidance. His passing leaves a hole in our family that simply cannot be filled.

The outpouring of love and support from Watermark Brewing Company, the Pachyderm Pedalers, and our community has been overwhelming. Everyone who knew Howard loved him. He left behind nothing but good memories and kind words, a testament to the kind of man he was.

If you knew Howard, or if his story has touched you, please consider donating. Every bit of support, no matter how big or small, will give Cheryl the gift of time and stability as she begins to navigate life without the love of her life

With gratitude,

Regan Kingsley

Howard’s Daughter-in-Law