Richard Cunningham Woolfolk, Sr.

Richard Cunningham Woolfolk, Sr. passed away on Wednesday morning, September 17, 2025, surrounded by his three children and his brother. He was 65.

Born on February 7, 1960, in Cambridge, Maryland, he was the middle son of the late Edmund and Caroline Woolfolk.

After graduating from Cambridge-South Dorchester High School in 1978, he continued his studies and his athletic pursuits at Massanutten Miliary Academy, Catawba College in North Carolina, and finishing at Chesapeake College. He then launched his career in heavy construction equipment sales, following in his father’s footsteps at Elliot & Frantz, Inc.

Richie’s family was the most important part of his life. His favorite days were spent watching his children and grandsons play sports or babysitting his granddaughter who was the “Apple of his Eye”.

While family was important, music was a close second. If there was good live music in town, you could easily spot Richie in the crowd dancing and singing along. Richie ended every day listening to his favorite live albums on his Alexa at his kitchen table.

God gifted Richie with a unique set of communication skills that drew all within earshot into conversation. He was passionate about his beliefs, and they radiated through every bone in his body. Richie’s Faith in God was strong, and he did not mind sharing it with all who would listen.

He is survived by his three children Jessica LeCompte (Sam), Sarah Lyons (James), and Richard Woolfolk, Jr.; his 4 grandchildren Sam, Jack, Wes and Meadow; and his brother W. David Woolfolk (Emily).

Besides his parents, he was preceded in death by his older brother, COL. Edmund W. Woolfolk, Jr.

Funeral services will be held for close friends and family at 2pm on October 17, 2025, at Christ Episcopal Church in Cambridge, followed by a celebration of life at the VFW Post 7460 at 3pm.

In lieu of flowers, the family suggests contributing to the Tunnel to Towers Foundation.

To share online condolences with the family, please visit www.newcombcollins.com.