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The Oldest Restaurant In Virginia Is Still Open After Almost 300 Years

Imagine having dinner at Virginia’s oldest restaurant, which has been welcoming hungry guests for nearly 300 years, even before the United States existed.

Over the centuries, it has welcomed travelers, witnessed major moments in American history, survived wars, and served some seriously famous guests.

That long history is still part of the experience today, with stone walls, crackling fireplaces, cozy dining rooms, and centuries of stories all around you.

So, where exactly is this nearly 300-year-old spot, and what makes it worth a visit today?

Where Is It?

The Red Fox Inn & Tavern is located at 2 East Washington Street in Middleburg, a small town in Loudoun County in Northern Virginia.

It’s about 35 minutes by car from Dulles International Airport, 45 minutes from Winchester, and roughly an hour from Washington, D.C.

About

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The Red Fox Inn & Tavern is one of Middleburg’s best-known landmarks, combining a restaurant, tavern, and boutique inn under one roof.

Its historic exterior features stone walls, white-trimmed windows, tall chimneys, dark metal roofs, and a peaceful courtyard surrounded by greenery.

Inside, expect a cozy setting with wooden floors, fireplaces, classic furniture, and plenty of details that remind you just how old the building is.

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The Tavern is the main attraction if you’re coming for a meal, with dining rooms that feel much more intimate than a big modern restaurant.

You can try a four-course dinner that moves from fried squash blossoms and Boston Bibb salad to grilled lamb rack, followed by mango panna cotta for dessert.

For something more casual, head to the Night Fox Pub for bar snacks and drinks like the Crenshaw Spritz, Clark Kent, Old Fashioned, or a local Virginia beer.

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And if you’re not ready to leave after dinner or drinks, you can turn your visit into an overnight stay too.

The Red Fox Inn has guest rooms, suites, and cottages tucked across five historic buildings, giving you several cozy options to choose from.

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You can stay right above the Tavern in a Red Fox suite, choose the quieter Stray Fox, or book the private Middleburg Cottage with its own courtyard access.

Each space has its own layout and classic character, with antique-inspired furnishings that make it feel more personal than a typical hotel room.

History

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So, how did The Red Fox Inn & Tavern become such a long-running Virginia landmark?

The story begins in 1728, when Joseph Chinn built a fieldstone tavern called Chinn’s Ordinary as a stopping point for travelers, horsemen, and farmers.

That means the property has been welcoming people for nearly 300 years.

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It even predates Middleburg itself, which was founded in 1763, and is considered one of the oldest continuously operated inns in the state.

Things changed dramatically for the building when the Civil War reached the area.

Both Union and Confederate forces occupied the property as control of Middleburg changed hands, and it was also used as a field hospital for wounded soldiers.

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By the late 1800s, Middleburg was becoming famous for foxhunting and horse breeding, turning the area into the heart of Virginia hunt country.

The inn became part of that growing culture, serving as a gathering place for the area’s social and sporting scene.

It was then saved from demolition in 1937, remodeled, and renamed The Red Fox Inn & Tavern as a nod to the area’s hunting traditions.

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From there, the property only grew more famous, attracting some seriously well-known guests throughout the 20th century.

John F. Kennedy once held a press conference here, while Jacqueline Kennedy Onassis often visited during the fall.

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Elizabeth Taylor also regularly stopped by for dinner, joining a guest list that included Paul Newman, Tom Cruise, and Robert Duvall.

Today, the historic inn continues welcoming guests for dinner and overnight stays, keeping its centuries-old tradition alive.

Know Before You Go

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Hours

The Dining Room serves dinner from 4:30 to 8 PM Monday through Thursday, with hours extended to 8:30 PM on Friday and Saturday.

The Pub opens a little earlier at 4 PM and stays open until 9 PM on weekdays and 9:30 PM on Friday and Saturday, with both closed on Sunday.

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Best Time to Visit

Spring and fall are fantastic times to plan your trip to The Red Fox Inn & Tavern, especially if you want to explore Virginia’s horse and wine country too.

April and May bring comfortable weather for sightseeing, while October is a great pick to catch the fall colors around Middleburg.

Just keep in mind that these seasons can get busy, so book dining and overnight stays early, especially around weekends, holidays, and major equestrian events.

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Things to Do Nearby

The Red Fox Inn & Tavern puts you close to plenty of things to see and do, making it easy to spend more time exploring the area.

You can spend some time shopping around Middleburg’s historic district, where you’ll find everything from equestrian gear and antiques to clothing boutiques, art, and gifts.

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If you’re curious about horses, fox hunting, polo, and other field sports, stop by the National Sporting Library & Museum, just a 5-minute walk from the inn.

For some fresh air and a short hike, head to Bears Den Overlook near Bluemont, where you’ll find a rocky viewpoint with wide views of the Shenandoah Valley.


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