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Olive Isobel Zimmerman (Gregory)

December 31, 1928 - October 11, 2025

Today we lost a Canadian pioneer!
Olive was born in Desford, MB and was raised near the farming community of Boissevain, MB. In 1950, after completing Home Economics training in Brandon, she responded to a newspaper ad for work at the Trans-Canada Motel and Restaurant at Westhawk Lake, MB. There, she met Adolph and they were married in 1951. They built and for 10 years operated, a tourist resort, Lakeside Cabins, on Westhawk Lake in the up and coming recreational area which would become the Whiteshell Provincial Park. They were innovators and by the spring of 1951, Lakeside had five cabins in a row and the lakeshore ones had electric lights (from a 32-volt Delco plant) and cold running water to kitchen sinks. They were deemed the most modern cabins in the Whiteshell! Many of the strangers that came to Lakeside for a week or two each summer became their lifelong friends.
In 1962, they sold Lakeside Cabins and built a new home at the Toniata Junction, between the townsites of Westhawk and Falcon Lakes. Olive went to work at another tourist resort, Tall Pine Lodges. She was also very active in the community through the Tea-Time Ladies Club in the early ‘50’s, West Hawk United Church, Toastmasters and the Birchwood Ladies Club. She did a lot of the organizing for the fall feast dinners and ‘Owl-i-days’ She was a contributor to the Whiteshell Echo paper for many years.
Olive was a gifted seamstress, quilter, knitter and crocheter. Her greatest joy came from helping others, whether it was teaching girls how to knit and sew, baking for the baking sales and fall dinners, mending someone’s clothes or sewing costumes. Our home was always open and there was always a place at the table for any and all of our friends. She also wrote and published a hardcover book, the History and Folklore of the Whiteshell Park – South, a collection of anecdotes from the early residents and cottagers who established the new park as a cottage country. This book is still in demand after a second printing and has become a cherished keepsake in many cottages of the Whiteshell.
In 1999, as the burden of living in the remoteness of the Park became too much for them, Adolph and Olive moved to Victoria to be closer to their children, grandchildren and great-grandchildren and to have a chance to have them more in their lives.
Unfortunately, dementia stole her personality, mobility and communication in the latter years of her life. She was a favourite of the staff members at Sidney All Care Residences, where she lived since 2018.
Olive was pre-deceased by her husband Adolph in 2011, her parents, siblings Ralph, George and Frances. She is survived by her youngest sister, Elizabeth (Oakbank, MB), children Wayne (Jo-Anne) and Audrey (Lewis), five grandchildren and seven great-grandchildren.
As Olive closed out the History and Folklore of the Whiteshell Park – South:
“The time has come to close the book –
Like closing the cottage each fall,
We will go back – for just one last look –
One last glance, one last memory, ….
Finally, this year it’s coming to ‘the End’.”
Be at peace, Mom.
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Condolence Messages

  1. Gail asper says

    October 17, 2025 at 9:03 pm

    It was with great sadness that I read of the passing of Olive. Truly the end of an era. Our family has had a cottage at Falcon Lake since 1962 and always depended on the Zimmermans for help in maintaining the cottage. Although it has been many years since I had the pleasure of seeing Olive I will always remember her as a feisty and kind individual who loved her family and loved the Whiteshell. As do I.
    Please accept my sincerest condolences on the passing of your remarkable mom. I do hope the many wonderful memories you have of her help ease the pain of your loss. If there is any charity I could make a donation to in Olives memory please let me know.
    With warmest regards, Gail Asper

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  2. Gail asper says

    October 17, 2025 at 9:07 pm

    PS- I would love to get a copy of Olive’s book on The Whiteshell if anyone has an extra copy!

    Reply
  3. Eric Winograd says

    October 18, 2025 at 2:16 pm

    We remember your mom and dad as being such nice people who help us city folk make our cottage our little heaven. I remember my mom looking forward to her annual coffee date with your mom. Your dad could fix anything. I am still out there and I could use him desperately. Eric Winograd and my sibs.

    Reply
  4. Sandra Wylie says

    October 21, 2025 at 7:51 am

    I have countless wonderful memories of my time spent with your Mum and Dad, at their Lion’s Cove home. The lunches, sharing the loaf “heal” with your Dad, stories from Manitoba, recipes(many became our family favorites), and sewing projects.
    She was the catalyst to encourage the children and staff from Tiny Tots Daycare to visit Lion’s Cove to share story time and do crafts, never taking maybe for an answer!
    Such a positive influence, mentor, truly a fabulous friend. You are correct, a true pioneer woman of her era! A proud legacy to cherish by all!
    Always in my heart

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