Last month’s mystery location: Willits, California
When looking outside from his split-level home on a half-acre in the Shenandoah Valley in New Market, Virginia, in a town where he’s lived all of his life, there’s contentment apparent in the voice and demeanor of 64-year-old Charles Day, a.k.a. Cowboy. Married to Mary for 44 years, he met his would-be bride when her sister was dating Charles’ older brother. While their siblings’ relationship didn’t last, both have married others and are themselves enjoying long marriages.
Charles and Mary didn’t have children until a dozen years after marrying. A similar template had occurred in Charles’ background. The couple’s daughters live nearby, the eldest a nurse and her younger sister a financial planner. Charlene Viola, 32, and Jacqueline Painter, 30, have both been married nine years, and as the father of the brides explained, “They were married within 45 days of each other.” When asked if the girls had families just yet, Charles explained, “No grandkids, but we have grand dogs.” He listed two schnauzers, a Boxer and a kitty.
As a longtime truck driver, Charles said that much of the American countryside he’d come to know was seen through a windshield. “I’d see a place and wish I could stop, but because I was driving truck and on a schedule, I couldn’t.”
Charles Day’s parents were born in 1909 and 1911, respectively. They married young but didn’t have Charles until February 1954. Charles’ mother’s mother was full-blooded Cherokee, yet Charles wasn’t raised to embrace the Native American heritage. He explained it was because, “In those days it wasn’t cool to be Native American.”
When Charles was maybe five, there was an old country store in the then-smaller town of New Market. Every little while the same lone biker would come into town and stop at the store. The man wore leather, and moved with a certain amount of confidence; some might say swagger. He’d get off his bike, go inside to do his business and then mount up to leave. Charles recalled watching in awe, “I was impressed. The man would fire up the Harley and take off,” leaving a kid to listen to the trailing sound of the rider running through the gears. “I loved that sound. He was here, then gone.”
Charles’ connection to the landscape and desire to better know it fused with those early biker memories and a desire to see America through a different windshield. In Virginia riders are required to get a learner’s permit and then ride with another motorcyclist, each on their own bike. Charles hadn’t yet taken the community college course when he spotted a 750 Kawasaki sitting alongside the road with a for sale sign. “They were asking more than I was willing to give,” he said. He left his name with the seller who phoned him after several days asking. “You still interested?” Charles said, “I am, but with two stipulations; throw in the two helmets and you’ll have to deliver it to me,” because Charles hadn’t yet taken the driver training. Mentor and friend Raymond was instrumental in getting Charles in the saddle. “Raymond helped me learn to ride.” Charles laughed at the humbling learning curve saying, “Here I’d driven tractor trailer, and all those gears…” but knew he needed to give the different conveyance its proper respect.
Bikes that have followed included a Kawasaki 1500 and then a 2007 (new) Vulcan.
When he retired from trucking in 1990, he was ready to spend even more time riding. But it would be several years until a Harley-Davidson came home to roost.
In 2015, inspired by friend Raymond’s 1992 Dyna, Charles sought out a Harley of his own. In June of that year, Charles Day found a 2009 Harley-Davidson up in Philadelphia, Pennsylvania, and drove the five hours to see it. It had 9,400 miles on the odometer and was like new. He bit. Before tucking it away when the snow hit this season, the gauge read 45,000. That’s well over 1,000 a month on average.
There are times Mary can’t make it, but she enjoys riding. Most road miles Charles has logged were with another passenger. Atop the luggage rack there’s a special carrier for a small riding companion, Skipper, a schnauzer.
Charles hasn’t retired altogether but operates from a home office selling financial products and real estate. He explained, “Every dollar I earn comes from commission and since I’m winding down, I work when I work, and play when I play.”
The plan ahead for he and Mary is to sell their home in the shadow of the Massanutten Mountains of the Appalachians, a home purchased in 1980, buy a toy hauler so they can travel with the Harley, and head west. “We’ve never toured Montana, Idaho, Washington or Oregon.”
Personal note to Charles: When you, Mary and Skipper tour NE Washington State, you’re all welcome to spend a little time on the farm here.
Until then, happy trails.

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