Dudley Simmons Waltrip

He was born to Dudley and Mary Waltrip in James City County and lived in the county his whole life. His love for construction started at a very young age while working side by side with his parents in their business. At the age of 14, and with the encouragement from a teacher, Timmy traded in his schoolbooks to work full time. One of his first jobs was digging the footings at Jamestown Festival Park. That was the beginning of many years of hard work and successful businesses.

With the love of his life, Becky, by his side, he began D.S. Waltrip & Sons, Inc. that flourished for over 50 years. His first big job was clearing the areas now known as Busch Gardens, and Kingsmill Resort and Golf Course. The work of Timmy lives on throughout Williamsburg and the surrounding areas. Areas like Colonial Williamsburg, including their Archeological Excavation work, clearing for New Town, Sentara Hospital, Riverside Hospital, on every military installation around the peninsula, and numerous other neighborhoods, business' and roads. He also built the Greensprings Mobile Home Park, Greensprings Grocery, and owned the Colony Square Laundromat.

In 1993, he was the founder and sole sponsor of Waltrip Racing. His son's Timmy 2 and Brian raced Go Karts, Champ Karts, and a Super Truck. The Waltrip Racing Team is still racing and carrying on the family tradition today.

Timmy was also a co-founder of the Williamsburg Jamestown Airport along with his parents and brother, Larry. T&L Disposal was another venture with his brother, Larry, and both businesses are still running today.

Many Friday nights, you would find Timmy at Charly's Airport Restaurant singing Blue Suede Shoes. During the day, taking naps in his favorite chair at the "Rat Shack" or weather permitting, his favorite was fishing with friends. Timmy also liked listening to country music, telling jokes, trapping and hunting.

Timmy loved his family and was so proud of his children, grandchildren, and great-grandchildren. He was happiest when the whole family was all together.

Timmy was preceded in death by his father, Dudley Clay Waltrip, mother, Mary Simmons Waltrip, and brother, Robert Simmons.

He is survived by his wife of 62 years, (as of May 13th), Rebecca R. Waltrip; daughter Mary Lisa Waltrip (Robbie); son Dudley S. (Timmy 2) Waltrip Jr.; son Brian Clay Waltrip (Simone); daughter Dena Leann Waltrip (Kip); nine grandchildren (Rebecca, Brandon, Amy, Dalton, Shelby, Hunter, Austin, Nicholas, Hannah); nine great-grandchildren (Marshall, Silas, Helen, Lily, Alex, Logan, Brantleigh, Raeleigh, and Braxton); and brother, Larry T. Waltrip.

Besides being a hard worker, he was generous and kind beyond measure. A man of his word and a hand shake was his bond. He was a "pilgrim passing through" as he said many times. He has passed through this life leaving an imprint throughout the community, but mainly on the hearts of his family and friends. He will be greatly missed.

Fond memories and expressions of sympathy may be shared at www.NelsenWilliamsburg.com for the Waltrip family.