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Nowhere is Christmas Celebrated with More Pomp, Circumstance, and Tradition.

Words by Christine VanDyk

Photos courtesy of Hugh Kenny, Derek Anderson

Eat, Stay, Shop in Virginia’s Hunt Country

A light blanket of snow covers the ground, evidence of the first dusting of winter. Mittened hands clutch steaming cups of coffee, while children chase each other through the sidewalks. The clip-clop of horses’ hooves signals that something has finally begun. Crimson-coated riders, baying hounds, and jolly old St. Nicholas usher in a parade straight out of a Charles Dickens novel.

This is Middleburg, Virginia, the horse and hunt capital of the nation, and nowhere is Christmas celebrated with more pomp, circumstance, and tradition.

The festivities kick off the first Friday of December with carolers singing “O Holy Night” as the Christmas tree sparks to life. The next morning, The Middleburg Hunt Review, known for its members’ scarlet jackets with apple-green collars, progresses up the street in a mile-long mounted spectacle of horses and hounds. It will be the first of two parades. The second is a community affair with bands, floats, and, of course, Santa Claus.

Few places evoke more charm than Middleburg, especially during the holidays. Less than an hour from the nation’s capital, the town sits along rolling pastures and two-lane country roads peppered with Federal-style homes. There are stone taverns and cozy fireplaces, equestrian mounts and tartan plaid. And whether you’re here for a girls’ weekend, family gathering, or romantic retreat, it’s the perfect way to celebrate the season and experience Middleburg for the holidays.

Where to Eat

Start with Common Grounds coffee while you plan the day in this relaxing, pet-friendly spot. Later, you’ll want to snag some ready-made sandwiches and picnic supplies at Locke Store & Buttery, a restaurant and country store. In the afternoon, The Red Fox Inn & Tavern delivers a cozy atmosphere that dates back to 1728 and is an ideal spot for relaxing with friends after a day of shopping. While the fine dining restaurant does offer a four-course dinner, the bar is just as welcoming on a winter’s evening. If you’re looking for the best happy hour, head to King Street Oyster Bar. Snag an outdoor table or sit at the bar and watch the staff shuck oysters⎯no less than 10 varieties, served within a day or two of being caught. Finally, grab a sweet treat or homemade pie from The Upper Crust before capping your evening with live music and nightcaps at The Red Horse Tavern, a no-frills bar serving up burgers, beer, and lively beats.

Few places evoke more charm than Middleburg, especially during the holidays. 

Where to Stay

The “unassuming lifestyle of the Virginia Piedmont” is what charmed former First Lady Jacqueline Kennedy about Middleburg. Fox hunting, horse racing, and polo playing made Old World stays like The Red Fox Inn & Tavern a favorite of Mrs. Kennedy. The inn features boutique accommodations, fine cuisine, and modern touches in a historic fieldstone setting. Just outside of town, the Salamander Middleburg Resort & Spa and Goodstone Inn offer a pastoral setting Jane Austen herself may have penned.

Where to Shop

In today’s world, it’s hard to find something truly special, but that’s not so in Middleburg. From antique stores to specialty shops, you’re sure to find the perfect present. Begin at Creme de la Creme, where you’ll browse fine French home goods, books, and signature candles. Highcliffe Clothiers is the spot for British and Scottish equestrian attire, while Brick & Mortar Mercantile is known for locally made provisions. Finally, what would the holidays be without decorations? The Christmas Sleigh features hand-blown ornaments, hand-painted nutcrackers, and authentic German gifts.

Where to Play

Virginia’s vineyards welcome you to the holiday season with musical events, signature tastings, and festive decorations. Some of our favorites include Chrysalis Vineyards, Boxwood Estate Winery, and nearby Bluemont Vineyard. For another form of libation, try the Defiance Cider Barn or Lost Barrel Brewing. No designated driver? Expedition Vintage Tours will chauffeur your group in a classic Land Rover.

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