A charming historic town, an unexpected sense of belonging, and the priceless gift of family time
“Make assumptions if you must, but make not the mistake of assuming that your assumption is always right.”
—Abhijit Naskar
It’s interesting how our minds make assumptions about a place before our feet ever arrive. That certainly happened to me when my husband, John, suggested we visit Shepherdstown this past July. Having spent considerable time traveling through West Virginia, I thought I already knew what to expect. I expected we would find a quiet town nestled among the scenic mountains of West Virginia, with perhaps a couple of quaint shops, a restaurant or two, and a bit of history tossed in for good measure. While all of that proved to be true, Shepherdstown exceeded every expectation I had constructed.
🗺️ Beyond First Impressions
The surprise began before we even reached town. Much of the drive carried us through Pennsylvania and Maryland before finally returning to West Virginia. Entering Shepherdstown, we were pleasantly surprised to see how the town embraces its historic roots while celebrating a vibrant community that warmly welcomes visitors. From flower-lined streets with signage supporting the local theater production and Shepherd University to the restored and well-maintained historic homes and old brick sidewalks, Shepherdstown radiated local pride.
Once unpacked and settled into the Airbnb, we headed out to explore West Virginia’s oldest town (a distinction it shares with Romney). Naturally we made our way to German Street, lined with dozens of 18th- and 19th- century colonial homes and buildings. It did not take long for German Street to reveal itself as the historical and commercial heartbeat of the town. While all this history was enough to hold our interest and challenge my assumptions, it was the hospitable warmth of the people that really won my heart.
🏘️ A Community That Welcomes You In
Everywhere we looked, people from different walks of life seemed genuinely comfortable there. It felt like a town where everyone had been invited to the table. The pace was a bit slower, but the businesses seemed intentionally woven into the fabric of community life rather than existing to attract tourists. By the end of our first evening, after dinner at Blue Moon Cafe, I realized my assumptions had quietly disappeared.
🛍️ The Best Souvenirs Aren’t Things
Another unexpected gift of the trip was having our adult daughter join us while her boyfriend was tied up with taking the bar exam in Massachusetts. Watching her climb into the backseat with her pillow, blanket, and what I used to call a “busy-bag” instantly carried me back to family vacations years ago. We laughed until we cried more than once during the trip. “Hill Road Trip 2026” became our defining rallying cry as we made our way around the town each day and traveled to the nearby historic sites of Antietam and Harper’s Ferry.
For a few days, we slipped back into the rhythm of family vacations from years ago. We compared ice cream at the two local ice cream shops—yes, both shops had gluten free cones for me! We discovered a hidden gem of a sandwich shop within walking distance of the apartment that looked more like a neighborhood market—another unexpected gluten-free find! We also discovered our daughter still loved to collect rocks as she once did as a little girl—only this time, she did not ask her Dad to carry her “treasures” in his pockets for hours on end as she used to. More than anything, the trip reminded me that the greatest gift of travel isn’t simply discovering new places. It’s discovering new ways to enjoy the people you love.
🏞️ Finding Quiet Along the River
One personal appreciation I had for the town was its close proximity to the C & O Canal Trail, a historic 184.5-mile-long trail that stretches from Washington, D.C. to Cumberland, Maryland. Each morning of our stay, I was able to head out to run along the quiet, hilly sidewalks of the town before the start of the business day and then cruise along the flat, crushed limestone trail, enjoying the natural beauty of the Potomac River. There is something magical about beginning the day surrounded by birdsong, rushing water, and deer and squirrels scurrying into the woods upon my approach.
☕️ Where Everyone Has a Place at the Table
On our final morning in town, my daughter and I visited the Shepherdstown Sweet Shop and Bakery for sandwiches, hot beverages, and a few treats for the road. As we waited, I found myself smiling. My daughter struck up a conversation with another customer about the art of cross stitching. The owner of a nearby shop stopped in to pick up coffee for herself and coworkers. A small group of women animatedly discussed a book they were reading. One man quietly worked on his laptop. Four employees—each different from the rest—greeted customers with the same friendliness. It struck me that this wasn’t simply a bakery. It was a gathering place. Each unique person seemed stitched into the same community quilt, different patches held together by threads of kindness and belonging.
Driving home afterwards, I couldn’t help but reflect that quite often the best souvenirs aren’t purchased in gift shops. They are the things we carry home instead: shared laughter, a deeper appreciation for places that still know how to build community, and the quiet dismantling of one more stereotype. Shepherdstown gently reminded me that the world is almost always more welcoming, kinder, richer, and far more complicated than a simple stereotype.
I hope to return to Shepherdstown someday. Some places quietly stitch themselves into the fabric of our own lives, and Shepherdstown has certainly become one of them. If I am fortunate, there will be more “Hill Roadtrips” in the years ahead. No matter how old our children become, the gift of their time remains one of life’s greatest treasures.
