In Loving Memory of 
Shirley R. Middleton
age 100
Lovingly remembered by her friend Betty Friesen, many nieces and cousins as well as their families.

Died
June 1, 2025
Riverview Health Centre
Winnipeg, Manitoba

Public Graveside Service
Monday, August 18, 2025
Killarney Cemetery
Killarney, Manitoba
6:30 p.m.

 

Donations in memory of Shirley may be made to 
Killarney United Church Box 9 Killarney, MB 
R0K 1G0  or the Killarney Foundation Box 1180 
Killarney, MB R0K 1G0.

An inimitable spirit has departed. At the age of 100 Shirley Rosser Middleton passed away peacefully June 1 2025.

Shirley was a proud third generation Killarneyite.

Shirley’s grandparents PJ & Flora Sherlock arrived in 1888.  Keenly active in the community they became instrumental in the development of the emerging town. 

Flora was a devoted member of the Women’s Association making quilts by hand for anyone in need.

PJ was the 1st CPR agent in the newly opened train station.  With the opening up of the prairies the train station was a hive of activity, the Killarney depot as the first stop for many emigrants on their way west.  Any newcomers arriving without a place to stay were welcomed into PJ and Flora’s warm home.  Anyone who could sing, teach or play an instrument were especially welcomed by PJ, a legendary recruiter of new talent for the Killarney Brass Band (PJ, the founder & conductor).  If a train stopped long enough he would scan the platform looking for music cases.  He would then use all his charm to persuade the owners to stop and take up residence…..and literally dozens of Easterners were persuaded.

Shirley’s parents Mabel & Alexander Middleton were also lynchpins of community spirit.

As founding members of the golf course their commitment was clear by their willingness to hand mow the links until an acquisition of sheep was made. Mabel, sharing her father PJ’s love of music, played in the Killarney Ladies Silver Band which performed far & wide, including the ill-fated steamboat ‘Shamrock’ on Lake Killarney.

Born in 1924 Shirley was their youngest child and only daughter.  It is clear from early pictures that Shirley’s characteristic impish outlook on life was already a defining trait.  With the whole third floor attic of the ‘Senator’s House’ as her playroom, swimming in the lake everyday then racing back to see the train come in all the while safe within the warm embrace of an extended family of caring characters, growing up in Killarney was clearly a ‘lark’.

The loss of her beloved father & grandmother in 1933 was life changing for Shirley and her 2 brothers Bob & Clare.  At just 9 years of age and in the middle of the Great Depression Shirley became a dedicated helpmate to her stalwart mother.

In 1941, the middle of WW II, Shirley graduated from high school and immediately wanted to help with the war effort.  Accompanied by her mother, Shirley traveled to Winnipeg to enlist in the Canadian Women’s Army Corps.  When asked by the woman colonel if she could go immediately into training Shirley answered that she needed to first take her mom home and put on the storm windows.

Army life agreed with Shirley.  Basic training in Winnipeg, Vermillion, & Montreal - learning how to take orders. Given the rank of Sergeant, off to administrative training in Ottawa - learning how to give orders. Sergeant Shirley Middleton eventually trained 100s of young women for their role in Canada’s armed forces.  Highlight memories include keeping her contingent smartly ‘in step’ in the memorial parades.  To Shirley marching music felt ‘like home’.

At war’s end Shirley returned home to Killarney and put her administrative training to use working at the municipal offices.  Initially helping her Aunt Maggie, Shirley eventually became secretary treasurer for the town. 

In the 1950s Shirley’s exhaustive curiosity was piqued by news of a new law firm in Winnipeg in search of an office manager.  Shirley was awarded the position and moved to Winnipeg where she lived for the next 38 years taking early retirement to return home to Killarney to take care of her ailing mother.

The 1980s saw Shirley elected to Killarney town council, a position in which she took the opportunity to put the whole town on “solid footing”, quite literally, as the installation and maintenance of sidewalks was the contribution of which she was most proud.

In 1999 at the age of 75 the desire for simplifying responsibilities led Shirley to move back to Winnipeg to share a home with longtime friend Betty Friesen.

2024 saw a major milestone: her 100th Birthday.  Surrounded by family and friends, Shirley celebrated her 100 years with the grace and humour that defined her life.

Shirley is a credit to her Killarney upbringing. A blend of pioneer gumption, depression era humour, small town neighbourliness, christian compassion, the warmth of a loving family and big sky curiosity. 

With her glorious smile and irrepressible sense of joy and curiosity, Shirley is beloved by many. 

Shirley stories & tributes gratefully welcomed at susie-robertson@hotmail.com

All are welcomed to a Celebration of Shirley’s Life - June 20 10:30am, Riverview Chapel, Riverview Health Centre, Winnipeg.  Memorial donations can be made to the Killarney United Church or the Killarney Foundation.