1927 – 2016

YARMOUTH — On Saturday, Dec. 10, Raymond William Penfold Jr., 89, crossed the finish line to his final victory. Ray succumbed to a recent decline in health and passed away at home with family. Although it may take him a while to earn those angel wings, there’s no doubt that Heaven will know he’s arrived!

Ray was born Nov. 16, 1927, in Portland, the only child of Ray Sr. and Helene DeWever Penfold. They resided in South Paris for a short time before moving to South Portland where Ray grew up and attended local schools, excelling in music, dance, theater and all sports. He went on to graduate from MCI, Pittsfield. He immediately enlisted in the U.S. Navy and while attending the Naval Academy Prep School, Ray won the Light Heavyweight Boxing Championship and played football for the Bainbridge Commodores.

Ray was a young man with many talents. He became a photographer for Columbia Studios where his duties included escorting their visiting starlets to Old Orchard Beach for dancing on the pier in the heyday of the big band era. He always remembered those fun times.

With a desire to work for himself, Ray began his successful career as an entrepreneur with Penfold Trucking Co. and Ra-Ma Equipment based in Pittston for many years before moving the business to Portland in 1977.  He operated the Exit 7 truck stop and made Yarmouth his home. In 1985, he founded his current family business, VIP Tour & Charter Bus Co.

His need for speed and passion for racing led him to a lifetime of stock car racing spanning 60 years, winning a track championship at Wiscasset in 1971 and 1985, forming Penfold Motorsports with son Bill, and competing in the NASCAR North Series, ending with a local mud truck racing championship at age 83!


Ray was charming and persuasive with a deep, rich voice, hearty laugh and a larger-than-life presence that would fill the room. He had a persevering spirit, determination and tenacity that lives on in his children of whom he was extremely proud and close to.

Ray was predeceased by his former wives, Lorraine Cummings, Roberta Penfold and Martha Penfold; and his sons, Gary Cummings and Ray Penfold III.

He is survived by his wife, Pat Penfold, of 31 years; his children, Bill Penfold of Oxford, Mark Cummings of Bath, Jay Cummings (Cindy) of Dresden, Lana Sawyer (Norman) of Yarmouth, Eileen Pacy (Bruce) of Kensington, N.H., Maureen Davis (Owen) of Yarmouth; eight grandchildren; several great-grandchildren, extended family, friends and beloved pets.

You may offer your condolences and share your stories with the family at www.lindquistfuneralhome.com.

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