You can smell the woodsmoke before you even see the fieldstone facade. That’s the thing about the Red Fox Inn & Tavern Middleburg—it doesn’t just sit on a street corner; it permeates the entire atmosphere of Washington Street. Established in 1728, it’s basically the oldest continuously operating inn in America, depending on who you ask and how they define "continuously."
It's old. Really old.
If these thick stone walls could talk, they’d probably tell you to put your phone away and drink some local Virginia cider. This isn't some corporate hotel chain trying to look "rustic" with distressed wood from a factory. This is the real deal. You feel it in the uneven floorboards that slant just enough to remind you that the ground has shifted over three centuries.
The History Isn't Just for Show
Joseph Chinn founded the place as Chinn's Ordinary. Back then, it was a literal waypoint for travelers heading between the Alexandria port and the Shenandoah Valley. George Washington actually slept here—not in a "George Washington slept everywhere" kind of way, but documented in his own journals as he surveyed the land for Lord Fairfax.
Think about that for a second.
The same stairs you’re walking up to get to your room were walked by a guy who hadn't even thought about becoming the first president yet. During the Civil War, the tavern took a darker turn, serving as a hospital for Confederate soldiers. Legend has it that Colonel John Mosby and his Rangers used the building as a frequent meeting spot, and it's even claimed that the tavern's taproom table was used as an operating table for wounded troops.
It’s heavy stuff, but that’s what gives the place its soul.
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Staying at the Red Fox Inn & Tavern Middleburg Today
If you’re expecting a generic lobby with a "breakfast included" sign and a flickering TV, you’re in the wrong town. Middleburg is the heart of Virginia's horse country, and the Red Fox reflects that elite, somewhat equestrian-obsessed culture. The guest rooms aren't all in one building. They’re scattered across the original Inn, the Middleburg House, and several other historic structures like the Stray Fox and the Night Owl.
Each room is different. Honestly, that’s the best part.
One room might have a massive four-poster bed that requires a literal step-stool to climb into, while another features a fireplace that actually works. They use Frette linens and Molton Brown toiletries because, despite the 18th-century vibes, people still want 21st-century luxury. It’s a weird, beautiful paradox. You’ve got hand-hewn beams above your head and high-speed Wi-Fi (though the thick stone walls sometimes give the signal a run for its money).
The Tavern Experience
The food is where things get serious. This isn't "pub grub." The Red Fox Inn & Tavern Middleburg serves a multi-course hunt country dinner that feels like a ritual.
The menu leans heavily into the local terroir. You’ll find things like:
- Creamy peanut soup (a Virginia staple that sounds weird until you try it)
- Pan-seared scallops with seasonal purees
- Local venison or prime cuts of beef
- The famous crab cakes that locals swear by
The Night Owl bar is the place to be if you want to feel like a local. It’s dark, cozy, and smells like expensive bourbon. It’s where people go after a long day of fox hunting or winery hopping to decompress. You’ll see people in muddy riding boots sitting next to tech execs from D.C. who are just trying to escape the Beltway for forty-eight hours.
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What Most People Get Wrong About Middleburg
A lot of visitors think Middleburg is just a playground for the ultra-wealthy. While it’s true that some of the most expensive real estate in the country is hidden behind those stone walls and rolling hills, the Red Fox is surprisingly accessible if you just want a drink or a good meal.
You don't need a pedigree to sit at the bar.
People also assume the Inn is haunted. While the staff is usually too professional to confirm or deny specific ghost sightings, travelers have reported the typical "old building" phenomena—strange drafts, footsteps when no one is there, and the general feeling that someone is watching you from the corner of the room. Is it ghosts? Or is it just the house settling? Honestly, in a place this old, it could be both.
The Logistics: Getting There and Staying Sane
Middleburg is about an hour west of D.C., but it feels like a different planet. There are no stoplights. Literally none. If you’re driving in, be prepared for two-lane roads and a lot of horses.
Parking at the Inn can be a bit of a puzzle. Because the buildings date back to a time when people arrived on horses, there wasn't exactly a master plan for a parking garage. They have spots, but if you’re coming on a busy Saturday in October (peak season), give yourself some extra time to navigate the narrow side streets.
Pro tip: If you want the full experience, book a room in the original building. The rooms in the outlying cottages are gorgeous and often more spacious, but there’s something irreplaceable about staying in the same structure that has survived since 1728.
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Why the Hunt Country Aesthetic Matters
The Red Fox isn't just a business; it’s the anchor of the Middleburg Historic District. The town has fought hard to keep out the fast-food chains and the big-box retailers. When you walk out the front door of the tavern, you see local boutiques, art galleries specializing in sporting art (think lots of paintings of dogs and horses), and high-end antique shops.
It’s a curated experience of the American past.
For some, that might feel a bit stifling or overly "preppy." But for others, it’s a necessary respite from the frantic pace of modern life. There’s a certain rhythm to life here. Morning coffee at a local cafe, a hike through the nearby Sky Meadows State Park, a vineyard visit in the afternoon, and dinner at the Red Fox to close it out.
It works. It has worked for nearly 300 years.
Practical Steps for Your Visit
- Book Dinner Weeks in Advance: The Tavern is small and incredibly popular. If you show up on a Friday night without a reservation, you’re likely going to be eating a granola bar in your car.
- Check the Event Calendar: Middleburg goes hard for Christmas. The "Christmas in Middleburg" parade is world-famous and involves dozens of hounds and horses trotting right past the Red Fox. If you want to be there for that, you basically need to book a year out.
- Explore the Vineyards: You are in the heart of Loudoun County wine country. Boxwood Estate and Greenhill are both close by and offer top-tier Virginia wines that actually hold their own against West Coast labels.
- Pack for the Weather: Virginia is humid in the summer and can be surprisingly biting in the winter. The Inn is cozy, but you’ll be doing a lot of walking on brick sidewalks. Wear sensible shoes.
- Talk to the Staff: Many of the people working there have been around for years. They know the stories. They know which floorboard squeaks and which corner of the bar gets the best light at sunset.
The Red Fox Inn & Tavern Middleburg remains a landmark because it refuses to be anything other than what it is: a sturdy, stone-built testament to Virginia history that serves a mean cocktail and a comfortable bed. It doesn't need to chase trends. It just needs to keep the fire lit and the wine poured.
Check the official website for current seasonal menus, as the chef rotates offerings based on what's growing in the Piedmont region. If you're planning a mid-week trip, you'll find the town much quieter and the service at the tavern even more personal. Always confirm check-in times directly, as the multi-building layout means your "front desk" might be in a different spot than your actual room.
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