This storybook Virginia inn is tucked inside one of the oldest buildings in horse country

Nearly 300 years old, The Red Fox Inn & Tavern is the oldest building in Middleburg.

There are some hotels that stick with you—the ones with unbelievably soft bedding, breakfast buffets to write home about, or infinity pools with views you check out with dozens of pictures of. You think about your experiences, no matter how fleeting, time and time again, and you recommend the property to friends, family, and acquaintances without hesitation. As a travel writer, I’ve had more than a handful of stays that fall into this category, and one of my favorites is only about a two-hour drive from my home in Charlottesville, Virginia. 

A historic landmark, the building that now houses The Red Fox Inn & Tavern has stood proudly in downtown Middleburg since 1728, decades before the town itself was established. Its presence on Washington Street, the main thoroughfare, signals to visitors that they’ve officially arrived in the nation’s “Horse and Hunt Capital”—but its real charm (the thoughtful details, the history, the complete and utter coziness) goes beyond the stone facade.

The Accommodations

Upon checking into the inn, you’ll be directed to your accommodations. The entire property spans three acres, and it’s made up of several buildings that house the 22 rooms, suites, and cottages. Each building offers a slightly different look, feel, and experience—though you can expect varying shades of blue, brown, and safe—so it ultimately comes down to personal preference. 

The rooms in the historic Red Fox, right above the tavern and pub, have a quiet intimacy to them, but you’ll have a bit more privacy in the Stray Fox or the Fox Den, both located just a short walk from the main building. Walkways, courtyards, and gardens blooming with native Virginia plants keep the entire property feeling connected and cohesive.

The Culinary Experience

While it’s difficult to find fault in any of the uniquely decorated rooms, the real highlights of a stay at The Red Fox Inn & Tavern are culinary shaped. Mornings here start with a delightful breakfast delivery—think quiche and muffins paired with hot coffee and tea, which you can enjoy from the comfort of your own room. You’ll have to go off-property for lunch, but sandwiches from the quaint Middleburg Deli are right around the corner. After a day of antique shopping in Middleburg—don’t miss Federal & Black or Hastening Antiques—or exploring other corners of Virginia Hunt Country, return to Red Fox for the final meal of the day.

If you’re celebrating something special, go for the seasonal four-course prix fixe menu, billed as the Game & Seafood Dinner Experience, at the Dining Room in the Tavern. Or, if you’re feeling slightly less peckish, the more casual fare at The Night Fox Pub may better suit your fancy. Although the decidedly Virginia flavors and local ingredients impress all on their own, the atmosphere is really what sets the meal apart. Both The Dining Room and the pub are true gathering places, reminiscent of the building’s days as a Revolutionary War-era public house. The fireplace, stone walls, and ambient lighting, paired with hand-cut steaks, homemade desserts, and Virginia wine pairings, lull diners into a pleasant reverie.

And the best part? Your antique four-poster bed is either right upstairs—or only a short walk away.  Rooms at The Red Fox Inn & Tavern start at $395 per night.