We went to Middleburg four or five times a year as kids to have lunch. My parents had friends there. I loved the country life enough to think I might live there one day. I didn’t. Middleburg is still one of the prettiest places in Virginia.
Middleburg sits in the heart of Virginia’s hunt country — an hour west of Washington DC on US-50 through the rolling Loudoun County countryside, a village of about 700 people that has been one of the most sought-after addresses in the mid-Atlantic for generations. My parents had friends there and we went four or five times a year as kids for lunch. We ate at the Red Fox Inn, which has been feeding Middleburg visitors since 1728. I loved the country life enough as a child to think seriously about living there one day. I didn’t — small town life turned out not to be what I needed — but Middleburg is still one of the most beautiful places in Virginia, and the Red Fox Inn still serves lunch.
Is Middleburg Right for Your Trip?
The prettiest small town in Virginia — one hour from DC, a world away.
Red Fox Inn & Tavern
Operating since 1728 — one of the oldest continuously operating inns in America. Lunch in the tavern is the quintessential Middleburg experience. The building itself is fieldstone, low-ceilinged, colonial. Nothing about it feels performed.
Search HotelsWashington Street
Middleburg’s main street — antique shops, equestrian outfitters, art galleries, the Pink Box bakery, the National Sporting Library. A few blocks that take longer than they should because everything is worth looking at.
Search HotelsHunt Country Drive
The roads around Middleburg — Foxcroft Road, Sam Fred Road, Landmark School Road — are among the most beautiful in the mid-Atlantic. Rolling hills, stone walls, farm lanes, horse farms behind white fences. Drive them slowly.
Search HotelsLoudoun County Wineries
Loudoun County has over 40 wineries — the highest concentration in Virginia. Many are within 15 minutes of Middleburg. A Middleburg lunch followed by an afternoon at two or three wineries is the right day trip from DC.
Search HotelsThe Red Fox Inn
The Red Fox Inn & Tavern has been operating at the corner of Washington and Madison Streets in Middleburg since 1728 — making it one of the oldest continuously operating inns in the United States. The fieldstone building, the low ceilings, the tavern atmosphere are original.
We had lunch there four or five times a year as children and the experience was specific — the kind of place where the building itself is part of the meal, where the history is in the walls rather than displayed on plaques. Colonial Middleburg was a resting point for travelers on the road between Alexandria and the Shenandoah Valley, and the Red Fox served them then as it serves visitors now. The menu runs to Virginia classics — she-crab soup, Virginia ham, seasonal ingredients from local farms. Book in advance for weekends. redfox.com
Washington Street
Middleburg’s main street is two blocks long and takes considerably longer than that to walk properly. Antique shops with serious inventory, equestrian outfitters supplying the hunt country community, art galleries, the National Sporting Library & Museum (one of the finest collections of sporting art and literature in the world), the Pink Box bakery. Every business on Washington Street has been chosen rather than happened. The result is a main street that feels curated without feeling fake.
Hunt Country
Virginia’s hunt country is the rolling Piedmont landscape between the Blue Ridge and the DC suburbs — stone walls, white fences, horse farms, the specific visual grammar of a place that has been shaped by equestrian culture for two centuries.
The Middleburg Hunt dates to 1906. The Piedmont Fox Hounds go back even further. The hunt culture is not performative here — it is the actual fabric of the community, which is what makes the landscape look the way it does. Driving the roads around Middleburg — Foxcroft Road, the roads toward Upperville and The Plains — is one of the best free things you can do in northern Virginia.
The Upperville Colt & Horse Show in June is the oldest horse show in America — held every year since 1853 in the fields outside Upperville, 5 miles west of Middleburg. Open to the public, genuinely spectacular, and one of those events that most people who would love it have never heard of.
Loudoun County Wine Country
Loudoun County has more wineries than any other county in Virginia — over 40, concentrated in the rolling hills around Middleburg, Purcellville, and Leesburg. The combination of a Middleburg lunch and an afternoon at two or three Loudoun wineries is the right template for a DC day trip. Boxwood Estate, Chrysalis Vineyards, and Breaux Vineyards are among the most acclaimed.
Search Middleburg and Loudoun County Hotels
The Red Fox Inn has rooms above the tavern for the full Middleburg experience. Leesburg and the broader Loudoun County area has stronger hotel inventory for those doing the wine trail.
Quick Reference: Middleburg Virginia
| Category | The Answer |
|---|---|
| From DC | ~45 miles west via US-50 — about 1 hour in normal traffic |
| The lunch | Red Fox Inn & Tavern — since 1728, book in advance for weekends |
| The walk | Washington Street — 2 blocks, allow an hour |
| The drive | Foxcroft Road and roads toward Upperville — most beautiful in northern Virginia |
| Wine country | 40+ wineries in Loudoun County within 15 minutes |
| Annual event | Upperville Colt & Horse Show — June, oldest in America since 1853 |
| Population | ~700 year-round — very small, very specific, worth it |
| Best season | Spring (foaling season, everything green) and October (foliage, hunt season) |
I loved Middleburg enough as a child to think I might live there. The country life, the pretty roads, the Red Fox at lunch. I changed my mind — small town wasn’t for me in the end. But Middleburg didn’t change. An hour from DC and it’s still one of the prettiest places in Virginia, and the Red Fox still serves lunch, and the roads around the village are still some of the best to drive in the mid-Atlantic. That’s a place that knows what it is.