Diane Gray’s maternal grandfather, W.T. Oliver, was a housebuilder in Leaside and East York. He would purchase a lot or two, build houses on them, move into one, buy another few lots… rinse and repeat. He did this so often that his daughter, Irene, said she lived in 25 houses in the neighbourhood when she was growing up. One such pair built in 1940 was on Randolph Road at Kenrae. Interesting anomaly: a lane now extends from Lea Avenue to just behind the fire station at McRae between Sutherland and Randolph. This lane once travelled all the way to Millwood. For some unknown reason, that last part of the lane was removed, and everyone on that block picked up their garages and turned them around to face their respective streets.
When WWII broke out, Diane’s father, Fred Cook, signed up. Off he went to Newfoundland, but further medical testing there sent him back home. Two pieces of good news came of this: He was able to marry his sweetheart, Irene Oliver, in 1942 and they could move into one of her father’s houses – the one at 104 Randolph. It was here that Diane, their daughter, and her siblings grew up. During the war, her mother worked at Canada Wire and Cable and was a member of their rifle club. Her father worked for the Town of Leaside, and at the time of the original amalgamation of Leaside and East York in 1967, he was the town clerk.
Diane tells stories of going over to the train tracks behind where the curling club is now located, and building caves, complete with “furniture” into the banks of the tracks. She and her friends were also adept at climbing up the backs of the big outdoor advertising signs – all without parental knowledge or worry, or so it seemed.
Rolph Road was a new school then, covering kindergarten to Grade 8. But home economics and “shop” were taught at Bessborough only, so when she was in Grades 7 and 8, she would troop over to Bessborough for those classes and then return to Rolph. After Leaside Gardens was built, there was free skating Tuesdays and Thursdays after school in the winter. Everyone brought their skates to school and then went directly to the arena for skate time. And once there was a good frost, the whole of Trace Manes Park turned into skating rinks – one with boards for shinny and a huge pad for pleasure skating.
By the time Diane was in high school, she had a Saturday job at Leaside Gardens. She and Mrs. Doyle ran the snack bar in the arena. The hours were 8 a.m. to 5 p.m., with no breaks, and all for the princely sum of 60 cents an hour for Diane!
Friendship with two others in kindergarten and then seven more in high school led to, what else, the Gab Girls. Their original get-togethers were monthly, but now, apart from the two who have died, the remaining eight continue to meet four or five times a year.
When Diane married Gibson (Gibby) Gray in 1968, her parents were still living in the Randolph house, and her Oliver grandmother was living in another W.T. Oliver house at 1367 Pape – just over the Leaside Bridge. Diane’s parents moved to the Pape house with her grandmother, while Gibby and Diane bought the Randolph house. They have since lived in Dwight, Ont., running the general store there, and in the Pape house, but are now back in Leaside – with a view of “their” Randolph house from their apartment. Leaside is home.
