Many readers of this story may be native to Northern Virginia and know every hamlet from the Potomac River to the Blue Ridge. But for transplants like me, every trip in the man-van has the potential to uncover something interesting and new. On a recent excursion beyond the D.C. suburbs we discovered the wonderful little town of Winchester, VA.

The plan had been simple and free of expectations: drive west and enjoy the fall colors while the boys took their naps. I had already laid the groundwork for a successful naptime by sapping their strength on a walk through the woods. After throwing stones in the creek and swinging and sliding at two neighborhood playgrounds, they were worn out. We fed them a quick lunch, buckled them into their seats, and both of them were sound asleep before we had even reached the Manassas exit on Hwy 66.

With no destination in mind, we decided to drive until the boys finished napping. We exited the freeway and rolled past the gas station in Old Tavern. The foothills, set against a crisp, blue sky, glowed with rich reds and golden yellow hues. Before long, we were heading north on Route 17 toward Winchester, enjoying adult conversation and gorgeous scenery along the way. The charming main street in Marshall deserved a stop, especially the Marshall Diner, but nothing was going to interrupt naptime.

Often on our weekend day trips, we stop at wineries to sample the fruits of the vineyard. My wife and I looked longingly at the rows of grapevines as we passed Miracle Valley and Three Fox vineyards. The winery signs with the little purple grapes and an arrow pointing the way to some secluded Eden were everywhere.

We passed Hollin Farms, where we had purchased our pumpkins just a week earlier, and laughed at the memory of me chasing a runaway pumpkin down the steep slope after it escaped the wagon. My sons had nearly been blown off the mountainside as we picked fresh greens – or salad, as my boys called it.

The boys began to stir as we descended into the Shenandoah Valley. With lunch on our minds, the outskirts of Winchester didn’t look too appetizing. But as we followed signs for Old Town Winchester, the strip malls disappeared and the town’s character began to emerge. What a pleasant surprise! We had found the type of town for which we are always searching. Preserved brick buildings and quiet streets lined with houses with wrap-around porches displayed the town’s winning personality. Civil War plaques and historical markers presented the town’s proud history to visitors like us. And unique restaurants and shops lined the extremely kid-friendly pedestrian mall.

After a brief wine tasting at Murphy Beverage Company – oh yes, we did - we enjoyed a surprisingly good meal at Brewbakers Restaurant. The hyperbolic description for the shrimp bisque wasn’t overstating the truth when it promised, “you’ll be hooked.” Polite, attentive servers, tasteful Halloween decorations, a diverse menu, an outdoor seating area, and great food – this was our kind of eatery.

After wandering through the pedestrian mall, befriending a guitarist, tackling a stuffed giraffe, and purchasing some homemade pumpkin bread, we drove to Jim Barnett Park and unleashed the boys on two mammoth playgrounds, including the Children’s Dream accessible playground. When we finally left town, it was with a feeling of satisfaction and contentment. Two rested boys and a quiet country drive would’ve been considered a successful outing, but discovering an exciting new town to explore, completely by chance, made the day memorable. After reading about the town’s other offerings, I know that Winchester hasn’t seen the last of the Kaiser clan.

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Matthew Kaiser shares humorous stories about the lighter side of life on his blog, www.deliberatelyunintentional.blogspot.com. He lives in Springfield, VA with his beautiful wife and two young sons. This e-mail address is being protected from spambots. You need JavaScript enabled to view it