Jay Ollerenshaw

Jay Richard Ollerenshaw was born in Portland, Oregon, on June 4th, 1939, to Violet and Jack Ollerenshaw. He passed away peacefully on May 10, 2025. He was raised in Portland and grew up across the street from Rose City Cemetery. After graduating from Grant High School in 1958 he attended one year of college. Jay was married to the love of his life, Cheryl, from 1968 until her passing in 1999.

He undertook many entrepreneurial endeavors, owned a service station and countless properties, commercially fished, and managed Rose City Cemetery. Jay’s first job was mowing lawns at age 12 at the cemetery.

He is the oldest of three and is survived by his sister Sue Doctor and brother Jon Ollerenshaw; his 2 children, Jan Petrella and Justin Ollerenshaw; and four beautiful grandchildren, Blaine and Mia Petrella, and Raley and Eli Ollerenshaw. Jay was preceded in death by his wife, Cheryl and first born son, Blaine Ollerenshaw.

Jay grew up hunting, fishing and camping. Jay had a passion for music and enjoyed traveling to Bluegrass festivals. He was funny, caring and an all around good ol’ boy. He often said he wasn’t smart but he was the guy you went to if you wanted something fixed. In fact, his motto was, “why pay someone to do something you can do yourself”.

As we all know, after his wife Cheryl, his biggest love was boating. He began his boating life first as a power boater; commercial fishing in the late 60’s with his wife Cheryl. Jay would work all week, then drive out to Illwaco at 4:00 in the morning on Saturday to go fish. Jay may have missed the birth of one of his children because of his dedication to fishing!

In the early 80’s Jay and Cheryl bought their first sailboat, a Newport 30’, named “Carnival”. Jay and the family spent a few summers on the “Carnival” in the puget sound, and participated in Portland's Christmas ship fleet. Prior to being members of Portland Yacht Club (PYC), Jay and Cheryl were members of the Sauvie Island Yacht Club (SIYC). One of his favorite memories was sailing "Sovereign" in The Pacific Cup race to Hawaii in 1992.

As Jay reflected on his life, he was very proud of all of the things he accomplished and often said, "I had a good life!"

May the wind be ever at your back, fair weather and godspeed!