Cover photo for Dorothy Jean Shepherd's Obituary
Dorothy Jean Shepherd Profile Photo
1927 Dorothy 2022

Dorothy Jean Shepherd

March 25, 1927 — August 3, 2022



Dorothy “Dot” Jean (Colaw) Shepherd, 95, of Monterey, passed away Wednesday, August 3, 2022 at The Legacy at North Augusta in Staunton.

She was born in Blue Grass, on March 25, 1927, a daughter of the late George Edward and Virgie Belle (Swecker) Colaw.

An avid basketball player, Dot attended Blue Grass Schools and would recount memories of playing Monterey (Blue Grass’ rivals) in a no-holds-barred, dirt court match-up in skirted uniforms with spectators watching from the beds of nearby pick-up trucks. When she wasn’t in school, she helped on the family farm located in Blue Grass and, on occasion, got into a bit of mischief with her siblings. And though she was often found working in the fields, Dot also possessed a softer side and was a beautiful lady, which was highlighted when she was crowned princess of Highland County’s Bicentennial Celebration. Following graduation, Dot attended Dunsmore Business School in Staunton and continued playing basketball there.

First and foremost, Dot’s truest love was always her family. She embraced motherhood when she welcomed her babies to the world, and her whole life revolved around being a loving mother and providing for her children.


After raising her family, Dot became the director of the Highland Senior Center, who for over 30 years coordinated activities for the “Golden Oldies.” She was also a member of the Highland County Ladies Auxiliary, Blue Grass Ruritan Club and assisted the Highland Masonic Lodge #110 with their blood drives.


She was also a dedicated fan of The Statler Brothers. In fact, the Statler Brothers were a fan of hers, too, and they sent her a signed Christmas card every year to show their admiration. 


Her grandchildren knew her well and loved her dearly, as did her great-grandchildren. She taught them the importance of love of family — a value they all carry with them and profusely practice in her honor. Other appreciations her grandchildren gleaned from her? The art of having pancakes for dinner and a love of lumpy mashed potatoes. In later years, when you visited Dot’s home, you were immediately met with a hug that lovingly transcended into a death-grip on the hand or forearm. You were then either told to sit down, at which point she would continue to love on you, or you were served food and expected to eat it, whether you were hungry or not. 


Dot was known to have held a special place in her heart for all children, especially babies. She never passed up the opportunity to hold one, loving each as her own. In fact, as her eyesight began to fail her in her late 80s, that didn’t stop her from seeing a baby arrive through the doors at any of Monterey’s Restaurants.


Holding a deep love for her community, Dot greeted everyone with her beautiful smile and sparkling eyes. She was the epitome of love and goodness and was held dear to many as a beloved mother, grandmother, sister, aunt, cousin, and friend.


Surviving family members include her daughters, Somers Stephenson and husband, Steve Fullerton and Charlotte Stephenson and husband, Richard Shamrock, all of Monterey; son, Tom Stephenson of Monterey; step-daughter, Elizabeth S. Conn of Fredericksburg; step-son, David W. Shepherd III of Lynchburg; brother, John David Colaw and wife, Christine “Crissy” of Bolar; seven grandchildren, Crysta, Erica, David and Dorothy Stephenson as well as Aaron and Adam Whitelaw and Danny Fullerton;  six great-grandchildren, Rebecca and Suzanna Landrum, Andrew and Alyssa Whitelaw and Haley and Sadie Warner; as well as a great-great-grandchild due in November. Dot also greatly treasured her other numerous cousins and extended family members.


In addition to her parents and husband, Austin L. Shepherd, she was predeceased by sons, Frank Colaw Stephenson and Boyd Wilson “Steve” Stephenson, Jr.; great-granddaughter, Elizabeth Whitelaw; sisters, Rebecca “Becky” Ann Hull, Virginia “Ginny” Curry and Mary “Mug” Margaret Ruddick; and brothers, Paul, Wayne Edward, Cyrus D. and George “Goog” Colaw.


A funeral service will be held at 2 p.m. on Sunday, August 7, 2022 at Obaugh Funeral Home with pastor Chip Hill officiating. Burial will follow in Blue Grass Cemetery.


Family will receive friends prior to the service, starting at 12:30 p.m. at the funeral home.


Active pallbearers will be David Stephenson, Aaron and Adam Whitelaw, Jerry Moats, Dan Cohn, Nick Hooke, Richard Waybright, and Jody Colaw.


Memorial contributions may be sent to the Highland County Volunteer Rescue Squad, PO Box 268, Monterey, Va. 24465 or to the Blue Grass Ruritan Club, PO Box 52, Blue Grass, Va. 24413.

To order memorial trees or send flowers to the family in memory of Dorothy Jean Shepherd, please visit our flower store.

Service Schedule

Past Services


Sunday, August 7, 2022

12:30 - 2:00 pm (Eastern time)

Obaugh Funeral Home - Highland County

8739 Highland Turnpike, McDowell, VA 24458

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.

Funeral Service

Sunday, August 7, 2022

Starts at 2:00 pm (Eastern time)

Obaugh Funeral Home - Highland County

8739 Highland Turnpike, McDowell, VA 24458

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.


Sunday, August 7, 2022

Starts at 3:15 pm (Eastern time)

Blue Grass Cemetery Road

Blue Grass, VA 24413

Enter your phone number above to have directions sent via text. Standard text messaging rates apply.


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