Middleburg

Lush, lavish and rustically elegant, Middleburg became known as the “Horse and Hunt Capital of the Nation” in the early 1900s and gained a reputation as a luxury retreat for the Washington elite in the ‘60s. But its auspicious beginnings actually date back to a stone tavern built in 1728. That tavern, the Red Fox Inn and Tavern, remains the oldest continuously operating inn in the United States and now serves as an iconic—and symbolic—landmark for the Town of Middleburg.

Somphane Jones, a Realtor with Pearson Smith Realty and Loudoun County resident, describes Middleburg as, “a gorgeous, upscale place packed with understated luxury, but it’s more about the atmosphere. Take the Red Fox Inn. The food is phenomenal, but it’s so cozy and warm, that it transports you to another place. No matter when I’m there, it just feels like fall.”

The feeling that you can step into another time or place defines Middleburg so well. The homes themselves are like a choose-your-own-adventure book. For example, picture yourself downtown in a stately 1830 Federal-style brick manor house with five bedrooms, a broad circular driveway and an original stone smokehouse—the price tag is $1.7 million, but the experience is priceless. Or, for $500,000, write your story in a renovated two-bedroom cottage built in the late 1700s. If 1920s bungalows are your preferred genre, find one on a tree-lined block with three bedrooms and 2,000 square feet for $1.5 million. Want to spin a simple rural yarn? Head to the hills for a two-bedroom, 800-square-foot Cape Cod on a half-are for $425,000, or enjoy modern upgrades in a late 1800s farmhouse with three bedrooms and 1,500 square feet for $575,000. If your imagination is inspired by a historic horse farm anchored by a sprawling 1900 estate home with four bedrooms and more than 4,000 square feet, it’s yours for $3.4 million or more. You can tell equally tantalizing tales with a range of contemporary custom homes and planned communities offering a median list price of over $1 million.

Whatever your chosen adventure, historic downtown will play a leading role. Many buildings date from the late 1700s through the mid-1800s and announce themselves with bright awnings and decorative shingle signs. Jones calls downtown “the destination for eats and boutiques,” and it’s easy to see why. The commercial center buzzes with eclectic boutiques, high-end clothiers, equestrian shops and fine arts galleries. Dining options are everywhere. You can satisfy your seafood cravings at King Street Oyster Bar or dig into hearty pub fare at the Red Horse Tavern. Of course, you’ll need food for home, so Safeway provides your daily staples.

Schools are also plentiful. Students can attend Loudoun County Public Schools like Banneker Elementary, which offers robust arts, music and gifted learning programs. Blue Ridge Middle School features more than 65 student clubs, and Loudoun Valley High School provides a Capstone program focused on post-secondary success. Each school receives an A-minus rating from Niche.

When school’s out, Middleburg provides the penultimate natural playgrounds. Visit Mickie Gordon Memorial Park, featuring 100 acres of sporting grounds, fishing ponds and picnic pavilions, or hike historic trails across open meadows and a 200-year-old bridge at the Battle of Uppersville Historic Park. Franklin Park offers 203 acres with athletic fields, a playground, fishing, equestrian facilities, picnic pavilions, a performing arts center and an outdoor pool. The historically elegant Middleburg Community Center also provides a pool, social events, classes and seasonal celebrations in town.

For equestrian enthusiasts, Middleburg is nationally recognized for its annual events, including Christmas in Middleburg, where hounds lead horses and riders in full hunt regalia through town. You can also attend the Middleburg Spring Races or the Virginia Fall Races; catch America’s oldest horse show, the Upperville Horse and Colt Show; or explore the region's rich equine heritage at the National Sporting Library and Museum.

And for those that like pampered play, wineries, breweries and luxury inns like the Salamander Resort and Spa or Good Stone Inn and Restaurant dot the countryside and provide breathtaking views and upscale experiences.

No matter the story you want to tell, Middleburg will help you weave a narrative filled with natural beauty, padded with some pampering and steeped in historical adventure. Visit for a day—and you may stay a lifetime.

Written By

Anna Strock

Photography Contributed By

David MacNeill

Video By

Alex Finneran