A Toast to History: Inside the Oldest Bar in Virginia

While many colonial ordinaries have been lost to time or fire, one legendary establishment in Middleburg has kept its doors open and its hearth burning for nearly 300 years.

The title of the oldest continuously operating tavern in the Commonwealth of Virginia belongs to The Red Fox Inn & Tavern.

The Red Fox Inn & Tavern (Est. 1728)

Location: 2 East Washington Street, Middleburg, VA

Long before the United States was a country, the Red Fox Inn was serving weary travelers. Established in 1728 by Joseph Chinn (originally called "Chinn's Ordinary"), the tavern sat strategically at the halfway point between the port of Alexandria and the frontier town of Winchester.

For perspective: When this bar opened, George Washington wasn't even born yet.

A Guest List for the History Books

If the fieldstone walls of the Red Fox could talk, they would tell stories that sound like a high school history textbook come to life. The tavern has hosted a stunning array of American icons:

• George Washington: As a young surveyor in 1748, a 16-year-old Washington is said to have stopped at the tavern.
• Civil War Soldiers: During the Civil War, the tavern served as a hospital and a meeting place for Confederate Colonel John Mosby and his Rangers. In a grim twist of irony, the bar top was reportedly used as an operating table for wounded soldiers.
• The Kennedys: In the 20th century, the tavern became a favorite of the political elite. President John F. Kennedy held a press conference in the Jeb Stuart Room, and Jackie Kennedy frequently stayed at the inn during the fall foxhunting season.

The Atmosphere Today

Visiting The Red Fox today feels like stepping onto a movie set of colonial America. Located in the heart of Middleburg—the nation's "Horse and Hunt Capital"—the building retains its 18th-century charm.

• The Vibe: Expect thick stone walls, low ceilings with heavy timber beams, and roaring fireplaces that have warmed patrons for three centuries.
• The Drink: While you can certainly get a modern cocktail, the Night Fox Pub (the tavern's casual side) is the perfect place to sip a Virginia wine or a bourbon and imagine the conversations that took place in the corner booths 200 years ago.
• The Food: The menu leans into its "Hunt Country" roots, featuring Southern staples like peanut soup (a Virginia classic), crab cakes, and fried chicken.

Honorable Mentions

Determining the "oldest" can be tricky, depending on whether you count gaps in operation or building age. While The Red Fox holds the crown for 1728, two other Virginia bars deserve a nod:

• The Tavern (Abingdon, VA): Built in 1779, this is the oldest historic building in Abingdon. It famously hosted Andrew Jackson and Louis Philippe (the King of France). It is known today for its ghost stories and fine dining.
• Gadsby's Tavern (Alexandria, VA): While the current buildings date to 1785 and 1792, a tavern has operated on the lot since 1770. It was the setting for George Washington's Birthnight Balls and is now a hybrid operating restaurant and museum.

The Verdict

If you want to have a drink in the same spot where young George Washington rested his boots, and JFK held court, The Red Fox Inn & Tavern is the undisputed champion. It is a rare place where the past isn't just behind glass—it's something you can experience, one sip at a time.