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News > General > A stroll through the 1950s in photos

A stroll through the 1950s in photos

David Pickup OO takes us down memory lane with an array of photos taken during his school years in the 1950s.
14 Sep 2026
Written by Anna Evans
General

 A Pictorial Stroll Through Memories of the 1950s

R Williamson , MA , Headmaster from 1920 - 1958

 

Myself, left and brother Bernard on arrival at Oswestry School on a rainy day in 1952.  Posing as fashion icons under the trees on the playground, hoping to grow into the raincoats, against a backdrop of the School laboratory.

 

 

School House, our home for the next eight years, taken from the playground.

 

School House, taken from the lower paddock.

 

 

List of required necessities for life at the School

 

Panoramic view of the School taken from the upper reaches of a tree near the Quarry.

 

 

       

A chat with the Earl of Powys. As the youngest prizewinners on Speech Day 1953 myself left, aged 12 and brother Bernard 11, receive our prizes. I was reprimanded by my parents for appearing with my socks rolled down.

 

David, left, and Bernard, share a moment of contemplation in the dingle overlooking the open air swimming pool.

 

 

View of the lower paddock showing the School laboratory and the long wooden hut which served as the Prep Department, domain of Headmistress " Ma " Walton.

 

The School Dining Room.

The Headmaster's table was overlooked by a picture of the famous Dr Donne

 

The Senior Dormitory.   

Looking much like an army barracks, the dorm came alive after lights out, and the school bullies crawled out of their holes to torment us all. 

My bed was in the far left corner just below the primitive fire escape system attached to the wall, and many were the times I would have liked to try it out when forced, along with others, to run the gauntlet up and down the sides of the central batch of washbasins whilst being hit by anything from a pillow to a cricket stump by boys stationed at the end of their beds. These were moments when you discovered who your friends were !!!!

Oh, and by the way, as far as I remember, during my eight years as a boarder at School House we never held a fire drill. Roger Morgan, the daredevil that he was, is the only boy to try out this primitive escape system. Perhaps "old man" Williamson ought to have put Roger in charge of fire drills to prepare us all for such an eventuality.

 

 

Looking like a 13-year- old, bottom, left, I make it into the First XI only to experience defeat by our oldest enemy and arch rival, The Boys' High School.

 

This photo shows, far left, my brother Bernard and myself in the First XI cricket team, captained at that time by Peter Manford, bottom, centre,  an all round sportsman, whom I once surprised by overtaking him coming onto the playground to take second place at the end of the Final Triangle race. This was the second time I had come second, having previously come 2nd out of 40 during my year in the Prep Department in 1952. I would never go on to win it.

 

Outside the School gates on Upper Brook St used to be the starting point where the whole School assembled for the annual Final of The Triangle, introduced by Headmaster Williamson circa 1930 as part of his vision for it to become part of the School sporting curriculum. The start was slightly flawed by lining up the field with Juniors at the front, and after I was trampled underfoot and hospitalised for damage to both knees, the start was thereafter moved to The Maes -y- Llan.

 

 

In the final of the 220 yds race on Sports Day,1960, my brother, left, and I breached the tape together, and I was gutted when the result was given to Bernard. It was so close I thought that it should have been declared a dead heat. It still crops up in conversations today, such is the ongoing sibling rivalry. Coming first and second in this race was the final nail in the coffin for Holbache and Bernaby, and Oswald House was the overall winner of the games. 

 

In this picture, taken by a reporter from The Oswestry Advertizer, as captain of Oswald House, I can be seen accepting the House Cup on behalf of team Oswald whilst Headmaster Frankland looks on. School Athletics captain, RA " Tony " Hughes, who won every event in which he took part received the Victor Ludorum for the third year running. Tony was poorly treated by the British selection committee for the 1964 Olympics in Tokyo, as in the years leading up to the games he was regularly beating athletes who went on to be medal winners, yet he was not included in Great Britain squad.

 

Leaders of Team Oswald are pictured in the School Library surrounded by the spoils of victory from the 1960 games.

 

Here I am enjoying a quiet moment in celebration of Oswald's clean sweep in the games of 1960, by drinking from The House Cup.

 

The END.

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