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Roland John (Roly) Dobson

Posted By Egan Funeral Home On September 22, 2021 @ 9:05 am In Bolton Area,Obituaries | 77 Comments

Dobson Web

Peacefully, surrounded by his loving family, at Malton Village LTC, Mississauga, on Monday, September 20, 2021, Roly Dobson, in his 86th year, beloved husband for 52 years of Doris McCauley.  Loving father of John and Àsa, Susan and Wayne.  Grandfather of Kayden, Katelynn, Kaylee, Kyle, Daniel and Vanessa.  Dear brother of Lorraine (deceased), Art (deceased) and Janet, Kathleen and Tom (deceased), Elwood (deceased) and Shirley, Doreen (deceased), Marg and Gord.  Fondly remembered by his many nieces and nephews.  Roly grew up in Woodbridge on the farm.  In the mid seventies, he started his own excavation business and was well known for his expertise in the operation of heavy equipment, but mainly a backhoe.  Roly enjoyed his collection of antique cars and petroliana memorabilia.  Over the years, Roly enjoyed having his border collies around the farm.  He was proud of his home where many family Christmases and other functions were enjoyed.  He was full of wit and one liners.  Roly will be missed by many and forgotten by none. 

The family wishes to give a big thank you to all the staff of Malton Village LTC for all of their excellent care and loving support to both Roly and his family. 

Private funeral service and interment at Christ Church Anglican Cemetery, Woodbridge will take place.  A Celebration of Life will be held at a later date.  

If desired, memorial donations may be made to Malton Village LTC Family Council, 7075 Rexwood Road, Mississauga L4T 2W2. 

Condolences for the family may be offered at www.EganFuneralHome.com

Condolences for the family of “Roland John (Roly) Dobson”

Condolence from Susan on September 22nd, 2021 8:08 pm

1947 Claireville Public School

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Condolence from Susan on September 22nd, 2021 8:10 pm

Roly 1953 with Maggie & Dolly

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Condolence from Susan on September 22nd, 2021 8:12 pm

1956 Roly drove for Hugh Strachan Milk Transport.

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Condolence from Susan on September 22nd, 2021 8:13 pm

1966 Roly & Doris

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Condolence from Susan on September 22nd, 2021 8:14 pm

1967 Roly & Doris

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Condolence from Susan on September 22nd, 2021 8:15 pm

June 28th, 1969 Wedding Day

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Condolence from Doris on September 22nd, 2021 8:34 pm

June24, 1987 Toronto Island

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Condolence from Doris on September 22nd, 2021 8:35 pm

August 2005 Air Canada Center


Condolence from Doris on September 22nd, 2021 8:39 pm

Roly & Nipper1992

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Condolence from Doris on September 22nd, 2021 8:40 pm

December 17, 1986
First day with new 580E Case Backhoe


Condolence from Doris on September 22nd, 2021 8:42 pm

March 1, 2000 at Woodbridge


Condolence from Doris on September 22nd, 2021 8:45 pm

October 2009
Roly & border collie Chevy with 1946 Chevrolet 1/2 ton truck

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Condolence from Doris on September 22nd, 2021 8:46 pm

Roly parked at home

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Condolence from Doris on September 22nd, 2021 8:49 pm

January 15, 1992
Roly’s horseless carriage shop. Chevy’s bought, restored & kept.
Ford’s bought & sold

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Condolence from Doris on September 22nd, 2021 8:51 pm

1989 Two Roses & A Thorn


Condolence from Doris on September 22nd, 2021 8:56 pm

Another project completed by Roly.

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Condolence from Doris on September 22nd, 2021 9:00 pm

1999 Roly feeding pet chicken Rocks some grapes.
He had a soft spot for animals.


Condolence from Doris on September 22nd, 2021 9:03 pm

November 23, 2005
A man out standing in his field. Massey Harris dump rake and hay mower.


Condolence from Doris on September 22nd, 2021 9:05 pm

March 2006
Roly & Sally


Condolence from Doris on September 22nd, 2021 9:07 pm

Roly at home

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Condolence from Doris on September 22nd, 2021 9:08 pm

Roly & Wylie by the pool.

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Condolence from Doris on September 22nd, 2021 9:11 pm

July 1998 32 Chev in for an oil change.


Condolence from Doris on September 22nd, 2021 9:14 pm

September 1995 fueling 46 Chev truck


Condolence from Dave and Barb McCallum on September 22nd, 2021 9:16 pm

So sorry to hear about our good friend and sympathy to Doris and all the kids

Condolence from Doris on September 22nd, 2021 9:17 pm

December 18th, 1999.
Out celebrating Roly’s Birthday.

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Condolence from Osa on September 22nd, 2021 9:23 pm

June 2007
Roly & Sally


Condolence from Osa on September 22nd, 2021 9:25 pm



Condolence from Osa on September 22nd, 2021 10:42 pm

25th Wedding Anniversary

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Condolence from Osa on September 22nd, 2021 10:46 pm

2014 at home working around the yard.

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Condolence from Gary Bruce McKinnon on September 23rd, 2021 5:17 am

Roly and Doris were our neighbours for over 40 years and we could not have had better ones. I have lost count of the many hours we spent together either talking about current affairs or memories of the past. And I have also lost count of the many favours both gave us. As you know, Roly was very handy with a backhoe and whenever we required his services, he was only too happy to oblige and he insisted on no charge. Neighbours like him are rare indeed. In my mind I can still see him driving his big truck and backhoe either past our place or down Martin Grove Road to a new job site. My earliest recollection of him is when , back in the 1960’s, he helped my dad build a dam with his dozer. And when we pass by his former dwelling that he built many years ago these memories come to the fore. Rest in peace, a true loyal friend!

Condolence from Glen, Debbie, Meghan & Gene on September 23rd, 2021 8:12 am

Aunt Doris and Family,

We are saddened to hear about the loss of Uncle Roly but know he will now Rest In Peace. We have many fond memories which we will cherish. Thinking about you during this time.

Condolence from Betty Lou Vanderpost on September 23rd, 2021 9:16 am

Dear Doris & Family: Our deepest sympathy to you , John, Debbie and Susan in the loss of a dear husband and father. Roly always had a big smile on his face and was a kind and gentle man. Cherish the great memories. Rest In Peace Roly.

Hank & Betty Lou Vanderpost

Condolence from John and Sharon Rowe on September 23rd, 2021 10:27 am

Our deepest condolences to Doris and family. Our sincere thoughts are with you at this time.

John and Sharon Rowe and Family

Condolence from Ann Price on September 23rd, 2021 11:36 am

Great memories of Roly at SS#13 Public School and later from various functions through our lives. Great guy. Our condolences to Doris and family.
Trevor and Ann Price

Condolence from Paul & Maria Bertolacci on September 23rd, 2021 4:06 pm

Our deepest condolences on the loss of your dear husband, father, grandfather, uncle and friend. May he Rest in Peace.

Condolence from Marcia Bertolacci on September 23rd, 2021 4:10 pm

Condolences to my friend Susan and her family.

Condolence from Nadia G. on September 23rd, 2021 4:44 pm

Dear Doris and Family,

Please accept my most sincere condolences over the passing of Roly. He was such a jovial man with a big and joyful heart. Roly lived a very interesting life and was fortunate to have many wonderful experiences and adventures throughout the years. He definitely made memories that will last forever. He always had a twinkle in his charming blue eyes and made great and unexpected comebacks in conversations. Your home was filled with a wonderful sense of humor and so much laughter. Such a blessed life he lived! I will be keeping you all in my thoughts and prayers as you honor his life and lay him to rest. Know that he is with you always in spirit, no doubt smiling down on you all and becoming your greatest protector from the heavens above. Rest in peace sweet Roly…

Condolence from Tessa George on September 23rd, 2021 5:13 pm

I have fond memories of moments spent in conversations and sing-a-long with Roly. He lived at Malton Village for as many years as I have worked here and always had the ability to make me laugh. He will be missed!

Condolence from Sean, Carrie, Jake and Trent Weir on September 23rd, 2021 6:40 pm

Doris, John, Asa, Susan and family
We are very sorry for your loss

Roland Dobson

Condolence from Kim G on September 23rd, 2021 6:53 pm

My love to the family, and extended family.

Condolence from Dave and Linda Livingston on September 23rd, 2021 7:47 pm

Doris, John, Debbie and Susan,

Our sincere condolences to all of you on your recent loss. You’re in our thoughts but we know you’ll have many happy memories of Roly to reflect on during this difficult time.

Condolence from Charlene Sethi-Wong on September 23rd, 2021 8:56 pm

Our deepest condolences goes out to Doris and your family. Our thoughts and prayers are with you all during this difficult time. Sending our love,
Ignacio, Charlene and Mila Wong

Condolence from Bill, Sandy, Kayla and Brandon Veysey on September 23rd, 2021 9:53 pm

Aunt Doris and Family,

So sorry to hear of the passing of Uncle Roly. We are thinking of you all at this difficult time. Cherish the memories. Hugs to all!

Condolence from Christine Skara on September 23rd, 2021 10:30 pm

Mrs. Dobson, My fear friend Sue and Family
Sending you my deepest condolences and all my love during this difficult time. I will always remember Mr. Dobson’s smile and squinty eyes when he laughed. And he was always laughing and telling jokes. I always thought he was such a wonderful man. Im sure everyone who knew him feels the same way.
Stay strong for each other and hold the wonderful memories of a very special husband and father, in your heart. Xo
Beautiful photos !!!

Condolence from Susan, Jason, Alicia & Adam Dow on September 23rd, 2021 10:31 pm

Aunt Doris, John, Susan & Debbie

So very sorry for your loss. May all the wonderful memories help you through this difficult time.
RIP Uncle Roly

Condolence from Bernie, Ruth, and Family, and Gail & Kenny. on September 23rd, 2021 11:34 pm

Dear Doris and Family:
Roly’s passing has left lives forever changed. We may not be able to share a chat over a coffee at the kitchen table, meet up at an auction sale, or give a big wave as we pass by on Martin Grove Road. What we do have in common are lots of loving memories that we share, so when we gather from time to time, we will tell those tales of our days with Roly.

Roly, was a son, brother, husband, father, grandfather, uncle, brother-in-law. A mentor, historian, friend, collector, and neighbour, like no other. A farmer from a young age.

My memories of Roly range from the hay wagons to the milking of cows, his love of horses, and “Danny” the donkey on the farm. Shearing of the sheep, feeding baby lambs by bottle in the back porch of the little white house, and the ever present Border Collies.

Roly always maintained high standards and work ethics. Roly had an understanding and ability to debate any political party’s past or current policies. He had an appetite for home cooked meals and a sweet tooth, that could only be satisfied with a slice of pie or pastry.

Front and centre, Roly was smitten for Doris. Witnessed over fifty-two years together. Toward the end, when all else was failing Roly, he would still greet Doris with, “Well you’re looking good”.

His enormous zest for life, sense of humour, wit, and one liners, were obvious to all those who encountered Roly.

To Roly, “A big ten four”.

Condolence from Arun and Roma Sethi on September 23rd, 2021 11:48 pm

Our deepest condolences and heartfelt pray to Doris ,John and Asa,Susan and Wayne and the grand children. May the Lord bring peace and comfort to you.

Condolence from Noreen Farrell on September 24th, 2021 7:34 am

Dear Aunt Doris and Family,

We are saddened by your loss. Uncle Roly will be remembered by us for his big smile and hearty laugh!

Two wee Black Walnut trees were planted by Uncle Roly, on this property many years ago and now they

are robust. Our comforting thoughts and prayers are with each of you.

Condolence from Paul & Shelley McCallum on September 24th, 2021 9:45 am

Sorry to hear about Roly.

What a great guy! I member many fun parties at your house. I remember laughing till I was sore.
Love the backhoe pictures. He had an awesome collection of toys.

I can’t help but smile thinking about Roly today!

Condolence from Jim, Lisa, Cameron & Daniel Dobson on September 24th, 2021 10:36 am

To the Family – Our condolences on the passing of Roly. We are thinking of you.

Condolence from Al and Aletha ALBIN on September 24th, 2021 10:53 am

Dear Doris and Family
Our sincere thoughts and heartfelt prayers are with you and the whole family. The passing of a loved one leaves heartache no one can heal. LOVE leaves treasured memories no one can steal. Just wanted you aware, we care.
With condolence Al and Aletha Albin (curling)

Condolence from Cathy & Jim Van Noort on September 24th, 2021 10:00 pm

Aunt Doris & family,
We were so sadden to hear about the passing of Uncle Roly. We have lots of fond memories of Uncle Roly and we know he will be missed by all. Please know we are thinking of you all during this time.
Cathy & Jim & family

Condolence from Lou Cerruti on September 25th, 2021 9:03 am

To the Family,
Roly did a lot of excavation work removing and installing fuel tanks for me back in the mid 80’s at Penny & Casson. He was a true professional at his job. He was a good man. Always very calm and patient. I remember calling him and hoping that he was available to do the job because then I knew it was in good hands. Very sorry for your loss.

Condolence from Kayden,Katelynn,Kaylee on September 25th, 2021 11:00 am

We will miss you grandpa.

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Condolence from Kaylee on September 25th, 2021 11:05 am

We will miss visiting you and bringing you a treat.
You always called Katelynn and I little girl.

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Condolence from Myrlie on September 25th, 2021 1:36 pm

Condolences to Mrs. Dobson, Sue, Wayne, the grandchildren and the rest of the family on the passing of your husband, father and grandfather. May he rest in perfect peace.

Condolence from Alison on September 25th, 2021 2:54 pm

Dear Dobson Family,
Our deepest condolences to you all, in the passing of your dear husband, father and grandfather. I know that Roly was loved and cherished and he will be missed. Thinking of you as you grieve.
Alison & Sam Grima and family

Condolence from Doug and Kelly Bentley on September 25th, 2021 9:32 pm

Roly could work magic with the earth.
We met him in 1997 and had this unusual project we needed help with
Roly was our godsend.
With all his construction and common sense experience he new how to get things done.
He also welcomed us into his family and he became an uncle to our border collies Sparky and Sally.
When they stayed at the Dobson farm, Roly would ride his bicycle while they ran around the perimeter of his property. When we came to pick them up they never wanted to leave.
He could see things people couldn’t see and could find solutions to problems that people said couldn’t be solved. I once asked him on the job site how he spotted a tiny critter from the inside of his cab? His response was “you gotta know what you are looking for to see it”. With everything he knew he did have one shortcoming. That was the realization that the Ford truck was superior to the Chevy. Doug and Roly had fun bantering this back and forth for years.
We loved his spirit and will miss him very much.
We are forever grateful and privileged to have been his friend

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Condolence from Nancy Knecht on September 25th, 2021 10:18 pm

Dear Aunt Doris, John, Susan and the rest of your beautiful family,

The pictures you have posted are amazing! Thank you for sharing them with us. Uncle Roly was a kind, loving and joyful man. It was so much fun going to your place for many visits, celebrations and family reunions. I hope you will feel the peace that passes understanding that God will provide for you as you mourn the loss of your wonderful husband, father and grandfather. Uncle Roly was always there for his sisters. He was very willing to help my Mom (Doreen) when she needed him. She loved him so much! I will treasure my fond memories of him.



Condolence from Margaret Kelly on September 26th, 2021 11:55 am

To Doris, John and Susan-We were so sorry to read about Roly in the Saturday Star. We have many fond memories of him at all the family get-togethers at both your house in Woodbridge and ours. The last time we saw him would have been at Susan and Rich’s wedding in October, 2008. We offer our sincere condolences to all of you. May Roly rest in peace. From Margaret, Bob and family.

Condolence from Carolyn, Allan and Daniel Wadley on September 26th, 2021 5:47 pm

Dear Aunt Doris and Family,
We are sorry for your loss. While we were growing up, we heard many wonderful stories about what a caring brother Uncle Roly was to our mother Doreen. Through the years, we continued to see how he could be counted on when help was needed on the farm, all the while making the situation fun with jokes and his easy-going nature.
Uncle Roly was very special to us and we know he will be missed by many.

Condolence from Doug and Kelly Bentley on September 26th, 2021 8:07 pm

Gidleigh project, Woodbridge 1997

Roly 1

Condolence from Doug and Kelly Bentley on September 26th, 2021 8:09 pm

Gidleigh Project 1997, Woodbridge

Roly 2

Condolence from Gord and Lorraine Holdaway on September 26th, 2021 9:41 pm

We have known Rolly for 35 yrs.. We have had many hours of fun at horse shows and the many palomino meetings held at the Dobson home. Rolly was always a lot of fun on our trips to Branson, MO and Kentucky. We will always remember how happy he was at Malton Village LTC no matter what time we showed up. There were many parties there celebrating birthdays. We will miss him. Many condolences to Doris and famaily.

Condolence from Brenda and Dave Duncan on September 26th, 2021 9:48 pm

We will always remember Rolly with his smiling face and many jokes when we visited him. Our condolences to Doris and family. He will be missed by all.

Condolence from Gord and Lorraine Holdaway &Marie &Cliff Wismer on September 26th, 2021 10:01 pm

We have known Rolly for over 35 years. We have had many hours of fun at horse shows and the many palomino meetings held at the Dobson home. Rolly was always a lot of fun on our trips to Branson MO and Kentucky. WE will always remember how happy he was to see us at Malton Village LTC no matter how late we came, There were many parties there. We will miss him. Many condolences to Doris and family.

Condolence from Canadian Palomino Horse Association on September 26th, 2021 10:24 pm

Rolly was a member or the Canadian Palomino Horse Association. Many meeting were held at the Dobson home after which he shared memories of his vacation trips with Doris, especially the one in The Grand Canyon, and bringing an old truck back from out west. It was his way of telling the stories with great humor that made the stories memorable to all of us. He will always be remembered for his humor and one liners which many of them we never heard before. We always enjoyed the western music he played from his jute box. Rolly will be sadly missed by all. Our condolences to Doris and Family

Condolence from Jackie Potter on September 27th, 2021 8:39 am

Sadly, I just saw the notice in the newspaper about Roly’s passing. My mum, Molly Potter, was a resident at Malton Village for a number of years and Roly was her “neighbour”. When I would visit Mum, Roly was always there with a smile in the lunch room and would join in our conversations and share a Timbit or 2. Doris, I’m so sorry and sad for your loss. Roly was a gem and you were always a ray of sunshine & positivity for everyone at Malton Village. I always enjoyed seeing you and having our talks. I know you will miss him and that your heart must be breaking.
Be strong…please pass my condolences along to your family.

Best wishes, Jackie Potter.

Condolence from Doug McClure on September 27th, 2021 10:34 am

Hey Roly, you always had the most infectious laugh.
When looking at your picture, I can still hear it

Doug McClure

Condolence from Bonnie (Beckett) Leslie on September 27th, 2021 6:31 pm

Many fun times with Roly and his siblings both at their Dad’s farm in Woodbridge and their 100 acres in Bolton where my parents bought 3 of those acres and built a home. We saw the Dobsons many times when they made the trip to Bolton to check their cattle which were kept there in summer. My condolences to all of his family.

Condolence from Giorgina Schmider on September 28th, 2021 11:40 am

Rolly accomplished so much personally and professionally. He was loved and respected by so many. A life lived to its fullest.
Thinking of you during this difficult time. Please accept my heartfelt condolences.

Condolence from Pat Niepage on September 28th, 2021 1:24 pm

Dear Doris
Was sorry to hear of your loss. I am certainly a name from the past but wanted you to know that my sincere condolences go out to you and your family.
I lost my husband 16 years ago and still miss him today. Thank goodness for family and close friends. Gets easier as time goes by.
Take care

Condolence from Katelynn Charlton on September 30th, 2021 12:16 pm

We will miss the fun times we had at your place in Woodbridge. We will miss your funny jokes and how you made us all laugh around the table. Hope your enjoying lots of butterscotch ice cream in heaven.

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Condolence from Pauline Irish on October 3rd, 2021 1:11 pm

Lovely memories of Roly on our trip to Canada summer 1989. Love from the McMinn family of Claggan. Thinking of you all at this sad time. Xx
Anne, Jenny, Pauline, Robert and Sandra.

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Condolence from Pauline Irish on October 3rd, 2021 1:19 pm

All our love.

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Condolence from Pauline on October 3rd, 2021 4:55 pm

Fond memories of a lovely trip to Canada summer 1999. Meeting Roly and family was a real highlight. So sorry for your loss. All our love from the McMinn’s Claggan. Anne, Jenny, Pauline, Robert and Sandra. Xx

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Condolence from Glenn McCauley on October 5th, 2021 4:20 pm

I was just four years old when Roly married my sister. Twelve when my dad passed in nineteen seventy seven. What transpired form that point was Roly’s natural gift to mentor and fill that void of loss for me, while raising his own family.
I had the time of my life the four summers I spent living in the camper at the Woodbridge farm while working a summer job in the area. It was then that Roly took the time and showed me how to maintain a vehicle, paint a house, cut grass. All the fun loving parties spent by the pool side at his house. Our trip to Florida, where he and I bought tape recorders and played with them for hours. The endless time Roly spent, priceless to me.
Roly loved to play Santa Claus and one year he arrived dressed head to toe as such. And in his sac a train set, he even took the time to assemble it with me. Another year was a Sports Rod hockey game, hours of playing.
Memories of Roly and Doris coming home on New Year’s day all adorned with the hats on, horns blowing, noise makers, streamers around their neck and lots of good times and laughter.
Thank you Roly for all you did for me.

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