Highland County Generational Farmers – Dorothy Stephenson

Written By: Carly Thomas

*I recently sat down with Dorothy Stephenson to discuss being a young generational agriculturalist. This is the fourth installment of a four-part series on the subject: Generational Farming in Highland County.* 

Dorothy Stephenson is among the sixth generation to operate Glenwood, her family’s farm, and the ninth generation of her family to live in Highland County. She currently lives in Vanderpool with her feline fur baby, Loki. In addition to Glenwood, Dorothy is also a business woman in other respects. She owns and operates Sundance Media and Design, Sundance Studio & Productions, and this blog! 

Dorothy as a child helping work cattle at Glenwood.


Stephenson Family History

Dorothy’s family’s farm, which her fourth-great-grandfather Adam named “Glenwood,” is located in Meadowdale. However, her roots stretch back much farther, even across an ocean. While Adam was the first owner of Glenwood, her family has been in Highland County (or what eventually became Highland County) since the early 1740s, mostly settling in the Bolar, Meadowdale, and Hightown areas. 

“My sixth-great-grandfather and grandmother, William & Sarah, came to America shortly after getting married in County Donegal, Ireland,” Dorothy explains. “While we don’t know exactly why they decided to leave, come to America, and eventually settle in Virginia, we speculate that this area reminded them most of our home in Ireland — green, lush, with rolling hills and lots of prime land to live off of.” Dorothy continued, “Though we don’t know much about their lives in Ireland, we know William was born around 1705 and Sarah around 1710. They were married in Ulster, Ireland, in 1732 and took an estimated three-month journey to migrate to the New World shortly after. Following an approximate 10-year stent in Pennsylvania, they decided to move south, eventually landing in what would become Highland County.”  

Dorothy’s fourth-great-grandfather, Adam Stephenson, who was the original owner of Glenwood and is buried on the property, was one of the men who was instrumental in distinguishing and formally establishing Highland County. “Adam was the first clerk of Highland County and his family was among the first to settle in ‘Bell’s Place,’ the original name given to Monterey,” Dorothy explains. “After this time, he purchased Glenwood and moved to the property, establishing the first generation of our family farm.”  


Glenwood Now 

Dorothy currently runs cattle — cows, calves, steers, and heifers — on or nearby her ancestral land. “While my family has run cattle over the years, my grandfather also kept sheep,” Dorothy recalls. “At one point in Glenwood’s history, my great-great-aunt Susan “Sudie” Stephenson raised racing horses at Glenwood after her father and mother, Adam and Charlotte, passed the land to her.”  

However, Dorothy running cattle is not at all surprising as she is following in her father’s footsteps. Her father, Steve Stephenson, managed to build the farm into an extremely successful cattle operation. At its peak, Steve managed the sale of thousands of head at a time under the name “Glenwood Cattle Company,” which Dorothy retains today.

“I started running cattle as an adult in my early 20s — summer stocker steers” Dorothy says. “I eventually started a cow herd and endured all the blessings and pains that comes along with it — welcoming my own new baby calves, pulling some of them, losing a couple, and even getting smashed into the fence by a ticked off mama cow who almost broke my legs,” she recounted. 

Dorothy sitting her on her father, Steve’s, lap atop their faithful John Deere.

However, Dorothy’s biggest challenge came recently when her father, Steve, passed away in the fall of 2021. “I was very lucky to be able to pick up the phone and call him when I had a major question,” she says. “The answer, or at least a very educated opinion, was always easily ready. (Curse words included…)” she laughed. “That lifeline isn’t there anymore. He taught me a lot before he left and instilled in me (for better or worse) a boat-load of tenacity; however, I still have days that I want to pick up the phone and use him for a sounding board to further develop my cattle business.”

“The last two years before he passed were good ones,” she recalls with a smile. “He and I made an almost weekly ritual of salting the 85 head of steers he ran — a drop in the bucket of the many hundreds he ran when I was a child. This year, 2022, marks the first year I’m running those steers by myself. I have confidence in myself, but I miss him every time I head out to check cattle. And being the youngest Stephenson in the family, it’s not lost on me that when I go, I’ll be taking a huge chunk of our family legacy with me.” 


Agricultural Industry Advice

Despite the heartbreak of losing her father, Dorothy has these insights to those who are interested in the agriculture industry. “While it’s easy to be intimidated, don’t be,” she says. “There’s always something you’re not going to know. Learn as much as possible. Ask questions. And if you’re made to feel stupid because you don’t know an answer, brush it off. Try to keep the emotion out of it. Take the information you need and use it to better your operation and yourself. One day, you will know something someone else doesn’t. And when you’re asked a question, answer it with care and humility.” 

She continued: “Additionally, be honest and fair. Do unto others as you would have them do unto you. Because bad deeds WILL come back to bite you. Flipside, good deeds will also come back to you as well. If you conduct business in an honorable manner, one that you’re proud of, then you have nothing to worry about. Ultimately, look out for number one — you — but secondarily, and nearly equally important, look out for your good neighbors and fellow agriculturalists. And align yourself with people who do business in the same way.” 

Dorothy embraced by her Uncle Frank while Dorothy’s father, Steve, stands with Frank’s son and Steve’s nephew, David.


About the Author

Carly Thomas

Carly Thomas, a 2022 graduate of Highland High School, resides in the southern portion of Highland County. Growing up as the seventh generation to live on her family’s cattle ranch, Carly learned the importance of family, faith, and devotion to the land. She is passionate about FFA, agriculture, and supporting Highland County farmers. Carly enjoys being challenged and works in a variety of jobs from writing sports articles for her local newspaper to cooking at a local sandwich shop. She can often be found working on the ranch, riding horses with her father, or working on the next FFA activity.  



Related Articles

Fall 2022 Leaf Report – Round 2

Fall 2022 Leaf Report – Round 2

We've already seen a few snowflakes dancing around in the air. Is this a sign we're going to have a Highland County winter of old? Maybe... But for right now, our mountains are still popping, even on snow-cloud-overcast days! If you haven't made it to Highland to take...

Fall 2022 Leaf Report – Round 1

Fall 2022 Leaf Report – Round 1

Our Highland County mountains are putting on another show for us this year! Here are a few pictures from local photographers showing our county's current colors! I believe the mountains still have a lot of changing to do throughout the county, so stay tuned for next...

Highland County Generational Farmers – Christian Brock

Highland County Generational Farmers – Christian Brock

*I recently sat down with Christian Brock to discuss being a young generational agriculturalist. This is the third installment of a four-part series on the subject: Generational Farming in Highland County.*  Christian Brock is the fifth generation on the Brock Farm,...