Honor (And Anxiety) at the Highland County Horse Show

Written By: Dorothy Stephenson

In 1997, I received one of the greatest honors of my life. I carried the United States Flag on horseback to open the Highland County Fair Horse Show.

Highland County, Virginia, Highland County Fair, horse, horse show, horseman, horsemen, history, culture

Retired World War II Marine Mack Ratcliffe carrying the United States Flag on “Mountain Mama” at the 1993 Highland County Horse Show. (Photos courtesy the Highland County Fair Association.)

As a child, I would stand next to the fence to watch veteran horsemen Mack Ratcliffe – adorned in formal United States Marine Corp blues – and Jimmy Varner – dressed in suit, tie, and hat – present the Stars and Stripes with all the majesty the occasion demanded on tall, perfectly-postured American Saddlebreds. Of course, I also remember my father, Steve Stephenson, loping through the ring in full cowboy regalia with Old Glory unfurled and waving, vibrant and full of pride. 

For whatever reason, in the summer of ‘97, the horse show committee let me, a 13-year-old girl, who didn’t begin to add up to the aforementioned legends, carry our nation’s flag while “The Star-Spangled Banner” pulsed through the loudspeakers and the crowd rose to its feet.

To this day, I can’t help but get goosebumps when I think of the experience.

I had dreamed about representing our nation, our community, and my fellow horsemen this way since I was tiny. It was a dream I never thought would come true.

I mean, who was I to carry the flag? I was nothing but a skinny teenager with freckles and unruly auburn hair. My experience paled in comparison to the other riders in the ring. Seriously. Look at these men!

To say, I was honored was a huge understatement.


When Dad told me a few weeks before the show that I would be carrying the flag that year, I was initially speechless. Then, the nervousness set in. 

“Me??!!” I thought. “I have to practice!!”

Dad taught me how to balance the end of the flagpole on the top middle of my boot where my toes met my foot. 

Flag pole in hand, I asked my Quarter Horse mare, Carebear Charlee, to move forward at a walk. The first few steps went well until the vibration of Charlee’s steps began to move the flag pole on my foot. It slipped off…Fail.

I stopped Charlee, repositioned the pole on my boot, and tried again. Slip…Ahhhh!

I tried again, this time forcing the pole down painfully-hard on the top of my foot. Success.

Now, to try a jog… Ha! Slip! Geez.

Ok, more pressure on the flag pole, I thought.

Try again. Success!

“Can I try to lope?!” I enthusiastically asked Dad.

“Why don’t you just stick with what ya got?” He answered gruffly.


So, I practiced and practiced, and when the day came, I was nervous. Prepared, but nervous.

Back in the 90s, the iconic voice of Robin Sullenbarger flowed through the speakers to announce the Highland County Horse Show.

“Hello, everyone, and welcome to the 1997 Highland County Horse Show,” he started. “We’d like to open our show with the playing of the National Anthem. This year’s flag bearer will be Dorothy Stephenson.”

Here we gooooo, I thought, and with a deep breath, Charlee and I entered the ring.

When I heard those first few deep, rich notes of “The Star Spangled Banner” play through the speakers, I felt a lump in my throat. My eyes prickled with tears. I couldn’t believe what I was doing in that moment.

I wanted to lope, but I didn’t. I calmly carried the flag at a jog and raised my chin an extra inch as Charlee and I passed in front of the grandstand. With my head still held high, I dropped my gaze down and noticed little girls in cowboy boots standing next to the fence looking up at me with bright eyes. My eyes prickled more.

The anthem played as Charlee and I made our way around the ring. And, like all those who came before us, Charlee and I marched to the center of the ring and set up facing the grandstand to present our nation’s colors.

Highland County, Virginia, Highland County Fair, horse, horse show, horseman, horsemen, history, culture

Carrying the United States Flag on “Carebear Charlee” at the 1997 Highland County Horse Show. (Photo Courtesy the Highland County Fair Association.)

The anthem ended, and Charlee and I turned to exit the ring. As I passed through the gate, I handed the flag to Dad. As he took it, he grinned with pride and said, “You can breathe now.” I smiled back at him. 

When the Summer of 1998 came, Dad told me I’d be carrying the flag again. 

Better start practicing, I thought.

So Charlee and I saddled up, and I grabbed my practice pole. 

“Hang on a second,” Dad said, and he tossed me a little leather do-dad. I caught it, and looked up at him in confusion.

“What’s this?” I asked.

“It’s a boot,” he answered. “You attach it to the side of your stirrup, so you can put the end of the flag pole in it. It makes carrying the flag a whole lot easier.”

My jaw dropped. You’ve got to be kidding me, I thought.

“Why didn’t you give me this last year??” I asked my dad as he was walking away.

He turned and said with a grin, “Well, now, that would’ve been the easy way out.”


About the Author

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Dorothy Stephenson grew up on her family's cattle operation in Meadowdale, located in the southwest corner of Highland County. When she wasn't on horseback helping her father gather and work cattle, you'd likely find her (still on horseback) jumping creeks in her family's nearby "Big Pasture." Today, though she doesn't ride horses much anymore, she has her own cattle, land, and expansion plans for a farm. Additionally, (and with the inherited, Stephenson, entrepreneurial spirit) she owns two small businesses in Highland County - Sundance Media & Design and Sundance Studio & Productions, which houses another of Dorothy's long-time loves - Clogging. Dorothy loves exploring new places, skills, and ideas, and she intends to live life to the fullest as long as it will let her. (Oh! And she LOVES Christmas!)


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