The South’s Most Charming Christmas Town

Nowhere else does the holidays quite like Middleburg, Virginia


Seasonal splendor meets hunt-country history in Middleburg.

Founded in 1787 by a Revolutionary War officer in the rolling hills of Northern Virginia, postcard-perfect Middleburg (population about 830) has long been known
as a hub of horses, hounds, and foxhunting. Come the holiday season, the historic village, with its Federal-style houses, shops, and inns, also exudes the kind of Christmas charm that seems straight out of a Merchant Ivory movie.

Surrounded by stone-walled horse farms, Middleburg sits about an hour from Washington, D.C., and the first weekend of December marks the town’s official holiday celebration.  The tradition dates back to 1914, when Miss Charlotte (Haxall Noland) opened the doors of the elite Foxcroft School—boarding not only the daughters of the Carnegie, Roosevelt, and Rockefeller ilk but their horses, too—and the students began presenting the community with a Christmas pageant. Some four decades ago, the town tacked on a parade, coinciding with the Middleburg Hunt Review, a spectacle of pomp and pageantry.

These days more than ten thousand holiday merrymakers (many with pups clad in scarves, antlers, and elf hats in tow) attend the annual festivities. Here’s how to make the most of the spirited weekend.

Friday, November 30

The celebration kicks off with the Christmas Tree Lighting (5:00 p.m.) in the garden of the visitors’ center, a.k.a. the Pink Box, a tiny brick house two centuries old. Mugs of hot chocolate and local cider accompany an invocation and caroling in the glow of the town’s forty-five-foot-tall live spruce. “Imagine a hundred and fifty people all standing there singing ‘fahoo fores,’” says Christmas in Middleburg organizer Jim Herbert.

Saturday, December 1

This is the big day. You might want to spend the morning strolling the shops downtown to polish off your Christmas list. A small family-owned department store (the mayor’s family, no less), the Fun Shop stocks a little bit of everything, from toys to fox-themed bar glasses. But make sure to secure a spot along Washington Street, the town’s main thoroughfare, before 11:00 a.m. for the start of the first of the day’s two showstoppers, the Middleburg Hunt Review, a parade staged by the town’s longstanding foxhunting club. The club was the result of a well-publicized 1905 showdown between Harry Smith’s American hounds and Henry Higginson’s English pack. Smith’s hounds came out on top, but Middleburg was the big winner, claiming its position as America’s premier hunt country.

Photo: JODI & KURT

The Middleburg Hunt Review, a parade staged by the town’s longstanding foxhunting club.

Each year, the group gathers behind the Red Fox Inn, a charming stone beacon founded in 1728, to tip back a ceremonial port or sherry before the start of the review. Between the Middleburg Hunt members attired in scarlet or black coats with apple-green collars and brass buttons, and their guests, upwards of 120 riders on horseback flanked by Middleburg’s famous pack of forty American foxhounds process down the two-lane main street. Bonus points if white flakes are fluttering down to create a snow-dome effect on this Rockwellian vision.


The Red Fox Inn.

Once the pack has passed, walk west to the National Sporting Library & Museum, the clubby home to some eight hundred works of art chronicling equestrian and field pursuits, as well as rare books. The elevated campus is ideally situated for watching the second of the day’s main events—the 2:00 p.m. Christmas Parade—and spectators are invited to bring a chair and set up on the lawn. Other good vantage points include the Middleburg Common Grounds coffee shop’s street-side terrace (try the Harvest latte) and the Red Horse Tavern, a pub with a raised porch and plenty of local beer on tap.

A source of great civic pride, the parade includes a mile and a half of decked-out floats, formations of bagpipers, drummers, bands of all stripes, and more than seven hundred animals proceeding down Washington Street. Polo, pony, and hunt clubs, groups of Tennessee walking horses and standardbreds, llamas and alpacas, and the Middleburg Charro Club all strut their stuff. As for dogs, you’ll find greyhounds, a beagle pack, a corgi corps, and several dozen powerful white Great Pyrenees (part of the Appalachian Great Pyrenees Rescue), a breed of gentle giants that have traditionally guarded flocks of sheep deep in the mountains.

Mixed in among them are politicos, Harley riders, farmers, winemakers, and beauty queens. Middleburg’s Santa guides a spectacular team of Ayrshire grays, mighty draft horses in their unusual “pickax” carriage rig—three across the front and two in back.

Shake off the afternoon chill with a mug of Mt. Defiance Cidery & Distillery’s hot buttered rum or (nonalcoholic) mulled cider, before settling in at one of Middleburg’s
newest additions, King Street Oyster Bar, to sample ten to twelve different kinds of oysters on the half shell. For heartier fare, head over to Hunter’s Head Tavern (in nearby Upperville). In a refit 1750s log cabin, this outpost of Ayrshire Farm serves such winter classics as shepherd’s pie, and braised short ribs with caramelized apple jus. Regulars swear by the liver and onions with house-cured bacon—and a table by the fireplace.


Mt. Defiance Cidery & Distillery’s Absinthe .

Sunday, December 2

The Foxcroft School’s wooded campus provides an unforgettable backdrop for its Christmas Pageant (2:00 p.m.), where first-years present a live-animal nativity scene. “We like to say our two donkeys, Nod and Demi, have the best jobs on campus,” says Cathy McGehee, the school’s head. “They get room and board and only have to work one day a year.”

For digs that feel as historic as the town, you can’t do better than the country-set Goodstone Inn, with its six cozy guesthouses and Virginia-inspired brasserie. Or bunk down in the secluded splendor of Salamander Resort & Spa, where if there’s snow on the ground, you can rent tubes or sleds to tackle the property’s rolling hills.

Can’t make the weekend? The town’s holiday enchantment lasts all month, or ring in the big days Middleburg style at the Red Fox Inn, which offers a five-course game dinner with a champagne (specifically, Greenhill Winery blanc de blancs) toast on Christmas Eve and New Year’s Eve.