Entering the town of Winchester, Virginia, is like taking a time-travel trip. My recent visit echoed that of Shawnee and other Native tribes that lived for thousands of years in what today is Frederick County and, more recently, by European explorers who came as early as 1606.

As I approached the miniscule city (population about 28,000), there was little hint of the treasure trove of history that lay ahead.

I passed through a phalanx of familiar chain stores and fast-food restaurants. Then, as suddenly as this mass of modernity had appeared, it disappeared. I found myself in another world — a history-rich setting that envelops visitors in the past without fuss or fanfare.

Arriving at Winchester is entering a time capsule. This is no artificially created commercial attraction. Rather, it’s a real place where important chapters of American history were written and remain.

What makes this immersion in earlier times so impressive is how it serves as a backdrop for the memories that were born there. One example: There are so many references to, and touches of, the presence of George Washington that by the time you leave town, you have new insight into the man behind the fame.

Washington’s life is closely intwined with the story of Winchester. He arrived at the tender age of 16 in 1748, four years after the town was founded, to help survey land.

During the next 10 years he went on to become commander of Virginia’s militia regiment, planned and oversaw construction of more than 80 forts to provide protection for settlers from attack, and was chosen to serve as a delegate in the House of Burgesses, representing Winchester and Frederick County.

Remnants of Fort Loudoun, which was Washington’s headquarters from 1756 to 1758, are among numerous traces of his time in the area. So is the tiny log-and-stone George Washington’s Office Museum, whose displays include his written orders to soldiers concerning “tippling” and “Rules of Civility and Decent Behavior,” which he wrote at age 14.

Other notable men and women, historic structures, and mesmerizing museums add to the appeal of Winchester and its surroundings.

A number of significant sites sit in the Winchester Historic District. It encompasses 1,116 buildings dating from the 18th to mid-20th centuries. They range from log buildings and early stone houses to Federal-style townhomes and elegant Victorian residences.

The heart of the district is marked by the stately Greek Revival Frederick County Courthouse. It was completed in 1840, just in time to serve as a hospital and prison for both the Union and Confederate armies. Graffiti on some walls dates back to the military occupation of the building, which today houses a Civil War museum.

Reminders of that conflict are scattered about the area like shotgun shells. That’s not surprising, because the town and county’s location as a transportation hub made it a highly contested prize. Six major battles raged there, and control of Winchester changed hands more than 70 times.

Visitors may relive those skirmishes at three Civil War museums, battlefields, remains of forts, and other sites. The home used by Stonewall Jackson as his headquarters during the winter of 1861-1862 contains a large collection of his personal objects and memorabilia.  

After admiring Jackson’s imposing office desk, and a smaller traveling version, I turned my attention to an unfamiliar Confederate flag. I learned that it’s the battle banner from which the more recognizable Confederate pennant evolved.

Even more intriguing to me was Jackson’s sword, which earned the nickname “Rusted Blade.” It turns out that Stonewall was not the most fastidious of self-groomers, and his lack of care extended to the ceremonial rapier. It rusted so badly that eventually he could not withdraw it from the scabbard.

After delving deeply into the Revolutionary and Civil War history of the Winchester area, I turned my attention to the variety of other attractions the destination offers. Food and beverages rank high on that list.

For many people, Frederick County, Virginia, means apples. The Shenandoah Valley was the largest apple-growing region in the country in the early 1800s. While that claim is no longer valid, the fruit continues to hold an important place in the region’s rich agricultural heritage.

Family-owned farms and farmers markets offer a cornucopia of locally grown fruit, vegetables, and meats. Pick-your-own orchards and micro-farms sell goods ranging from fresh produce and homemade baked wares to local crafts, goat-milk soap, and wine.

Outstanding wine, along with other libations, adds to the taste-bud treats available in the area. My sampling at the family-owned, award-winning Briede (pronounced BREE-day) Family Winery included its locally crafted wine-flavored ice cream.

A very different experience awaited at Misty Mountain Meadworks, which concocts the world’s oldest alcoholic beverage using Virginia honey. Where there are apples there is cider, and the English-style hard liquid is created from locally grown fruit.

Speaking of locally grown, that applies to Patsy Cline, the Winchester native who became a leading country and pop music singer whose professional career (1954-1963) was cut short when she died in a plane crash. Her modest house museum depicts the hardscrabble life she led before she became a local hero.

Heroes of various kinds have been part of the story of Winchester, Virginia (visitwinchesterva.com). Accounts of their lives are among a number of reasons to visit there — and, as I quickly learned, there are many more.


After gallivanting around the world, Victor Block still retains the travel bug. He believes that travel is the best possible education. A member of the Society of American Travel Writers, Victor loves to explore new destinations and cultures, and his stories about them have won a number of writing awards.

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