Kevin Jay Pinkerton of Leonardtown, Maryland, passed away peacefully at home on March 23, 2026, after a lengthy illness, with his wife and children by his side, holding his hands and accompanying him in his final moments.

Kevin was born to Everett David "Pink" Pinkerton and Mildred "Milli" Cipolloni (née Kruger) and grew up in St. Mary's County. From a young age, he was curious, inventive, and deeply connected to nature.

He graduated from Ryken High School in 1974 and studied Computer Science and Mathematics at St. Mary's College of Maryland. He built a long career in programming with Bendix and Honeywell at Webster Field, Compass Systems, and Navmar Applied Sciences, supporting Naval and Coast Guard operations. He retired in 2016 to farm full-time with his wife.

Kevin met his wife Cheryl Raum at the county fair and knew immediately she was the one. They were married for 41 years and built their home and life together on her family's farm.

He was a devoted father to Hannah and Eli, encouraging them to explore, learn, and follow their own paths. He lived an unconventional life, pursuing his many interests fully, including photography, building, and working with animals.

Kevin had a special connection to nature and formed a deep bond with the donkeys on the farm. He was kind, fair, and true to himself.

Kevin is survived by his wife of 41 years, Cheryl Pinkerton of Leonardtown; his daughter, Hannah Pinkerton of Monterrey, Mexico; his son, Eli Pinkerton (Alexandra Lindman) of Woodinville, Washington; his sister, Tammy Payne (Scott) of California, MD; his stepmother, Elizabeth Ann Pinkerton of California, MD; and his stepfather, Joseph Cipolloni Jr. of Willow Street, PA.

He was predeceased by his sister, Connie Louise Moore of Minneapolis, Minnesota, and his parents.
The family thanks Hospice of St. Mary's for their care and support.

In lieu of flowers, donations may be made to:

Hospice of St. Mary's
P.O. Box 625
Leonardtown, MD 20650
(Please designate checks to Hospice of St. Mary's)

or

Peaceful Valley Donkey Rescue, Inc.
P.O. Box 216
Miles, TX 76861

If you see a donkey, stop and say hello. If it replies, Kevin is probably having a laugh somewhere nearby.