Middleburg: The Crown Jewel Just Minutes from Look Up Farm

Why Virginia's Horse and Hunt Capital Makes The Perfect Neighbor for Your Estate

When you choose to make Look Up Farm your home, you're not just investing in 53 acres of pristine Virginia countryside—you're gaining access to one of America's most charming and sophisticated small towns. Just nine miles north of The Plains lies Middleburg, a destination that perfectly complements the luxury estate lifestyle with its unique blend of equestrian heritage, culinary excellence, and refined shopping.

A Town That Defines Hunt Country Elegance

Established in 1787 and known as the "Nation's Horse and Hunt Capital," Middleburg has long been the social and cultural heart of Virginia's Hunt Country. This teeny tiny town—its historic district spans less than a mile—manages to pack more charm, sophistication, and amenities per square foot than virtually any other small town in America.

The brick-lined streets, once frequented by Jackie Kennedy Onassis, maintain their historic character while hosting an impressive collection of modern luxuries. It's this balance of preservation and progress that makes Middleburg the perfect complement to Look Up Farm's own blend of Colonial tradition and contemporary comfort.

Culinary Excellence at Your Doorstep

For Look Up Farm residents who appreciate fine dining, Middleburg has evolved into a legitimate culinary destination. The town's restaurants, all locally owned, offer everything from farm-to-table gourmet dining to hearty tavern fare—ensuring that whether you're hosting business associates or enjoying a casual family dinner, the perfect venue is just minutes away.

The Red Fox Inn & Tavern, America's oldest continuously operated inn (established in 1728), anchors the dining scene with its modern Southern dishes featuring fresh Piedmont ingredients. The historic atmosphere provides the perfect setting for special occasions or when entertaining out-of-town guests.

For those seeking contemporary cuisine, Harrimans at the Salamander Resort delivers five-star dining with ingredients sourced from their onsite garden and local farms. Meanwhile, King Street Oyster Bar, voted one of the best oyster bars west of D.C., offers 12 varieties of oysters served within 24-48 hours of harvest—a casual spot beloved by locals for its daily happy hour.

The recent additions to Middleburg's dining scene reflect its evolving sophistication. Bluewater Cocina brings a beachy, subtropical atmosphere to downtown with its Mexican cuisine and craft cocktails, while Black Market offers Italian specialties in a handsome gourmet shop and dining room setting.

Shopping That Matches Your Lifestyle

While Look Up Farm provides the space and privacy for country living at its finest, Middleburg's boutiques ensure you're never far from world-class shopping. The town's Washington Street and surrounding blocks host a carefully curated selection of shops that reflect the area's equestrian heritage while catering to contemporary tastes.

Federal & Black, named one of the world's ten best new shops by The Shopkeepers, offers a country-inspired selection of antiques and accessories perfect for decorating your estate. Lou Lou Boutiques provides designer fashion for the stylish equestrian, while Highcliffe Clothiers ensures gentlemen are properly attired for Hunt Country's social calendar.

The arrival of Middleburg Books in 2023 filled a crucial gap, bringing author events and supper clubs to town in a charming circa-1750 building. For home décor and unique gifts, The Fun Shop and Christmas Sleigh offer hunt country accessories that celebrate the region's heritage.

Cultural Attractions That Enrich Country Living

Living near Middleburg means easy access to cultural amenities typically found only in major cities. The National Sporting Library & Museum serves as the nation's leading resource on equestrian and outdoor pursuits, featuring a fine art gallery and library with over 16,000 books—an invaluable resource for equestrian enthusiasts considering developing Look Up Farm's acreage.

The annual Middleburg Christmas parade.

The town hosts nationally recognized events throughout the year, including the prestigious Middleburg Film Festival, a major stop on the Oscar trail, and the annual Christmas in Middleburg parade, where horses and hounds lead a glittering procession through town—a tradition that Look Up Farm families can easily make their own.

World-Class Hospitality and Wellness

When friends and family visit your estate at Look Up Farm, Middleburg offers accommodation options that match your standards. The Salamander Resort & Spa, on 340 acres just outside town, provides a luxurious retreat with a state-of-the-art spa, equestrian facilities, and multiple dining venues. The Goodstone Inn & Restaurant, spread across 265 acres, offers intimate luxury with just 18 guest rooms and a superb Conservatory restaurant.

The prestigious Salamander Resort in nearby Middleburg features a state-of-the-art spa, equestrian facilities, and award-winning dining - all within easy reach of Look Up Farm

These facilities also serve Look Up Farm residents well for spa days, business meetings, or simply enjoying a change of scenery without traveling far from home.

The Wine Country Connection

Middleburg sits at the heart of Loudoun County's flourishing wine region, with several distinguished vineyards within easy reach of Look Up Farm. Greenhill Winery & Vineyard earned recognition when its Blanc de Blancs was included in the 2016 Academy Awards gift bag, while Boxwood Winery specializes in lush Bordeaux blends. Chrysalis Vineyards at The Ag District offers not just excellent Norton varietals but also local cheeses, jams, and charcuterie—perfect for stocking your pantry at Look Up Farm.

The Convenience Factor

Located just 35 minutes from Dulles International Airport and 45 miles from Washington, D.C., Middleburg provides Look Up Farm residents with the perfect buffer between country tranquility and urban accessibility. You can conduct business in the capital, catch an international flight, or attend a Kennedy Center performance, all while maintaining your primary residence in the peaceful countryside.

For daily needs, Middleburg offers everything from Middleburg Common Grounds for morning coffee to Upper Crust for fresh baked goods, and the beloved Middleburg Deli for quick lunches. The new Brick & Mortar Mercantile combines wine tasting with gift shopping, ensuring that entertaining at Look Up Farm is always well-supplied.

A Community That Complements Your Estate

Perhaps most importantly, Middleburg provides Look Up Farm residents with a ready-made community of like-minded neighbors who share an appreciation for equestrian traditions, land preservation, and the finer things in life. The town's calendar of hunt meets, steeplechase races, and social events offers countless opportunities to engage with Virginia Hunt Country society.

The Middleburg Spring Races at nearby Glenwood Park draw a sophisticated crowd each April, while the town's multiple fox hunting clubs maintain centuries-old traditions that define the character of the region. For Look Up Farm residents interested in equestrian pursuits, Middleburg provides not just proximity to events but access to the expertise, services, and social connections that make Hunt Country living so distinctive.

The Perfect Partnership

The relationship between Look Up Farm and Middleburg represents the best of Virginia Hunt Country living—the privacy and space of a substantial estate combined with easy access to a vibrant town that punches far above its weight in amenities and attractions. It's a partnership that enhances the value of your investment in Look Up Farm while enriching your daily life with convenience, culture, and community.

When you're ready to venture beyond your 53 acres, Middleburg awaits—close enough for spontaneous dinner plans, yet far enough to preserve the peaceful sanctuary of your estate. It's this balance that makes Look Up Farm not just a property, but a gateway to one of America's most distinctive lifestyles.