Middleburg’s pomp, pageantry, and pride make it Virginia’s most charming holiday town.

Bells jingle when you enter the shops on Washington Street in downtown Middleburg—even when it’s not the holidays. Known as Virginia’s fox hunting capital, the town resembles a Currier & Ives print, with its colonial architecture, picture-perfect landscape, and smiling shoppers. It’s a place where everybody knows your name, and welcomes you even if they don’t.

For decades, the well-heeled have moved to Middleburg to ride their horses and immerse themselves in small-town charm.
In 1906, local equestrians founded the Middleburg Hunt. In addition to being firmly entrenched in foxhunting, the group also works to preserve the pristine fields and forests surrounding the town. They inaugurated the Hunt & Hounds Review in 1972, a picturesque Christmas parade that showcases Middleburg’s riders and horses in formal riding attire—scarlet with apple-green collars and brass buttons with the initials MH—accompanied by a swirl of energetic foxhounds. Now, more than 50 years later, this holiday event—always the first weekend in December—is a nationwide sensation.
A Stride Back in Time
“From a community perspective, what makes Christmas in Middleburg unique is the opportunity to share the special nature of the town and the people who live here,” says Mayor Bridge Littleton. “There’s an incredible story around the equestrian aspect of Middleburg, and we really enjoy sharing this experience with other folks.”
Littleton describes his early Christmases growing up in Middleburg: “I remember as a kid in the 1970s, we had these typical 70s decorations with huge plastic bells, pink tinsel with big colored lights on the lampposts. It looked like Main Street America.”
Then, he says, Em Sharp entered the picture. A talented art teacher from the Hill School, Sharp hand-painted signs and hung them on the lamp- posts. In one fell swoop, she single handedly elevated Christmas in Middleburg from the glam of its disco ball days. “There’s an angel, an 1890s Englishman holding a goose, and Kris Kringle in red pajamas. On his naughty list she listed a bunch of folks from the town,” Littleton says, laughing. “And my father’s name is on it.”
Today, local retailers string garlands, wreaths, and lights until the streets are aglow. Inside are glittering trees, carols playing, and everywhere you look, there’s a horse, a fox, or a hound. “The town has a window decorating contest, and our businesses go all out,” he adds.

PLAYroom, a toys and games store, beckons visitors with a colorful display.

Huntmaster Richard Roberts, surrounded by foxhounds, prepares for the Hunt & Hounds Review.
Shopping & Strolling
For the uninitiated, a brief stop at The Pink Box, Middleburg’s official visitor center, is essential. There you’ll find info on the area’s shopping and dining best bets, plus hotels, activities, parade details, and cultural sites. Smack in the middle of town, it’s at the Middleburg Museum on Washington Street.
To make sure you’re sufficiently stoked with plenty of holiday spirit before the town parades begin, don’t miss The Christmas Sleigh, a shop along Washington Street that resembles a European Christmas market. Designed for the ultimate Yulephile, it’s packed with an inventory rarely found in American stores—from ornaments to decorations and crèche sets. “I came for love,” says owner Dieter Rausch, a native of Germany, when asked why he chose this quaint town to set up shop 20 years ago. He also stocks collectibles like Steinbach nutcrackers and Bavarian apparel, right out of The Sound of Music.
For gift-giving inspiration, Crème de la Crème is famous for their irresistible collection of fine French and Italian housewares, inspired objects, and gifts, along with brands that include Julie Vos jewelry, John Robshaw pillows, and Vietri cookware. Especially popular are its custom-blended ceramic urn candles in scents like Sea Salted Lemon and Tuscan Currant.
Just off the main drag is The Woolley Fox on Madison Street, a new-to-Middleburg shop that showcases a beautifully curated collection of artisan-made treasures, including jewelry, scarves, original paintings, leatherwork, ceramics, and more—all thoughtfully chosen and one-of-a-kind.
Build Your Itinerary
While the pièces de résistance are most definitely the Middleburg parades, there are other iconic town sites to consider adding to your itinerary. The National Sporting Library & Museum provides a window into the horse and hunt culture of this special region of the Commonwealth. Its collection includes a variety of media, portraying the beauty of Virginia’s landscape and the history of horse racing and fox hunting.
Arrive on Friday, December 1, to catch the O Holy Night Tree Lighting Ceremony at the Middleburg Museum at the Pink Box at 6:00 p.m. sharp. Look for carolers, hot cocoa, and a visit from Santa Claus. Or sign up for a custom wreath-making workshop, a DIY experience, at Nature Composed Garden Shop, where partici- pants create wreaths made from fresh boughs, pine cones, and bows and benefit from guidance thanks to owner Jenn Pineau and her creative team. The shop also makes the perfect spot to escape the winter chill and browse. Bookend your visit with a stop at Foxcroft School’s annual Christmas Pageant, presented by the New Girls, on Sunday, December 3. This decades-old tradition also features live animals, a chorale performance, and Santa making the town rounds.
Salamander Resort rolls out the gingerbread for the holidays in a gingerbread house making workshop. An expert pastry team provides a cookie house and a buffet of decorations for participants—from gum drops to white icing, jawbreakers, candy canes, and more. Each guest receives a chef’s apron to take home.
But to experience Middleburg in all its decked-out glory, take a guided horse-drawn carriage ride through town that departs from the Pink Box from Harmon’s Carriages.

Breakfast with Santa at the Middleburg

Foxhounds await their special moment at the Hunt & Hounds Review.
Weekend Festivities
Michelle and Doug Myer are the organizers of the Christmas in Middleburg festivities, including the Middleburg Community Parade that began in 1979. “People love to see these incredible equestrian folks for the Middleburg Hunt Parade,” says Michelle Meyer. “It’s a regal site and very historic. The huntsman comes through and calls the horses and foxhounds, leading everybody down the road.”
The town’s leaders added Breakfast with Santa to the parade and a tree lighting ceremony. Soon retailers, hotels, and restaurants joined in with food experiences and entertainment. Now Christ- mas in Middleburg is more than the Hunt Parade. It’s a weekend of fun and fellowship that kicks off the holiday season in style.
Today’s community parade is more than a mile long and features riders on Harley Davidsons, bagpipers, and antique firetrucks. There are llamas, corgis, and car groups. Local bands per- form, accompanied by school dance teams. Two fan favorites are the rock band from Shenandoah College and The Grinch Who Stole Christmas.
“It was always a small parade, with kids, farm equipment, and animals,” says Michelle Meyer. “But it got bigger and bigger, attracting national press, until we had about 15,000 people in 2019.” After a “Covid reset,” organizers imposed a 10,000 limit, which made everyone feel more comfortable and safety requirements sustainable. From dawn to dusk, Middleburg’s downtown roads are blocked for pedestrian traffic only.

Parade Day
On Saturday morning, head to the Middleburg Community Charter School for Breakfast with Santa that includes a variety of breakfast options, an online auction, raffle prizes, and photos with Mr. and Mrs. Claus. Others, dressed in their best “ugly” Christmas sweaters and stocking caps, congregate downtown, where the aroma of hot chocolate and homemade cookies wafts through the air.
Promptly at 11:00 a.m., there’s the unmistakable rumbling of horse’s hooves. The crowd goes silent, and then immediately erupts in cheers. The dashing huntsman Richard Roberts, flanked by his pack of adorable American foxhounds—some 40 strong—leads the members of the Middleburg Hunt down Main Street.
Air whooshes by as more than 150 equestrians dressed in breeches, riding coats, and derby bowlers, trot and canter along. This is the Middleburg Hunt & Hounds Review with young equestrians on ponies, seasoned veterans on handsome thoroughbreds, and women riding sidesaddle. With tails wagging on overdrive, happy hounds greet parade bystanders. The air is electric—with pomp, pageantry, and pride. When the last horses take off at a gallop, another red-coated huntsman brings up the rear, and everyone looks wistful to see it all end. When it’s over, the riders assemble on the grounds of Salamander Resort to load their animals into trailers. Canine snouts pop in and out of the tailgates like a fierce game of whack-a-mole.
At midday, people mingle around downtown, ordering from the many food trucks positioned along the streets. They’re waiting for the Middleburg Christmas Parade, which starts at 2:00. Barrel-shaped floats sail by from Boxwood Estate Winery and Greenhill Vineyards proudly represent Northern Virginia’s wine country. The Middleburg Charro Club, a Mexican equestrian group, spin their lassos and perform tricks, while Tennessee Walking horses prance, alpacas stroll, and beauty queens wave. A beagle brigade bounces by, then a gaggle of greyhounds, followed by a massive cloud of white—dozens of Great Pyrenees, noble guardians of sheep. At the end, America’s favorite North Pole resident rides by, atop a giant sleigh pulled by a mighty team of gray Ayrshires. All in all, nearly 1,000 animals proceed down Washington Street. Afterward, everyone is invited to the “Spirit of Middleburg,” where retailers host sales and wine tastings. “It’s such a great time,” says Meyer. “Once we get started, all the months and weeks of massive organization just melt away. To see kids smiling, and people in our town enjoying it, it’s just so worth it. Our hope is that it continues to be a lovely tradition and legacy for the town.”
Middleburg’s mayor agrees. “The feeling of that day is why I love Christmas in Middleburg,” says Littleton. “We all have wider smiles and a little extra joy in our hearts. Having the first parade in Loudoun County sets a great tone for the rest of the holiday season.”

Dine
The Goodstone Inn’s two restaurants showcase the fruits of this working farm. At The Conservatory, regionally inspired dishes, with many ingredients sourced on-site, offer guests a world-class gastronomic experience complemented by an extensive wine list, highlighting Virginia’s best as well as global selections. The Bistro is for guests who prefer a more laid-back atmosphere. From crab stacks to gazpacho and meatloaf, this is the inn’s answer to fine dining in casual comfort. 36205 Snake Hill Rd., Goodstone.com
King Street Oyster Bar, perfectly positioned for people-watching, enjoys a premier location along the town’s main street, and is especially popular during happy hour where discounted drinks, oysters, and apps are on the menu. 1 E. Washington St., KingStreetOysterBar.com
Red Fox Inn & Tavern, steeped in history, opened in 1728 and has hosted its fair share of who’s who-ers, including two presidents (George Washington and JFK) and the likes of Tom Cruise and Paul Newman, not to mention local celeb Robert Duvall. The tavern’s culinary team showcases locally sourced ingredients in a multi-course tasting menu with optional wine pairings, and the Night Fox Pub makes a cozy spot for craft cocktails and bar snacks. 2 E. Washington St., RedFox.com
Salamander Resort, 500 N. Pendleton St., SalamanderResort.com
- Harriman’s Grill overlooks the rolling valleys of Virginia’s legendary horse country, where Jackie Kennedy often rode her “favorite treasure” Black Jack. The restaurant has a casual feel, but the food is pure fine dining.
- Gold Cup Wine Bar menu includes Virginia wines and spirits along with handcrafted sandwiches.
- Market Salamander offers grab-and-go items, or an in-bistro or patio dining experience. With a delectable breakfast menu, handheld sandwiches, sharables, and salads for lunch and dinner. Plus, shop the market’s array of preserves, breads, and spreads.


festive menu at Harriman’s Grill features Chapel Hill Beef Short Ribs with polenta, black garlic, gremolata, and tiny vegetables.
Stay and Make it a Weekend
MIDDLEBURG FESTIVITIES continue throughout the month of December. For visitors staying overnight, the town has three hotels where guests can relax and recharge during the hectic holiday season.
- Just outside of Middleburg is the historic Goodstone Inn, known for its romantic cottages overlooking the Blue Ridge Mountains. On 256 acres of rolling hills, the property is a working farm, with cows, chickens, and a llama. Farm tours are available that focus on sustainability practices and the Inn’s impressive farm-to-table program that supports its two restaurants, The Conservatory and The Bistro. 36205 Snake Hill Rd., Goodstone.com
- For travelers wishing to stay closer to the action, Red Fox Inn & Tavern has a complex of sumptuous rooms in town, where restaurants and shops are just steps away. The inn was founded in the 1700s and boasts presidents, celebrities, and dignitaries among its guests. 2 E. Washington St., RedFox.com
- Salamander Resort resembles an elegant manor home with equestrian-themed spaces and a library full of books. Guests nestle around stone fireplaces sipping hot toddies and discussing the day’s hike, the Horse & Hounds Review, or tour of the stables. Rooms have fireplaces and views of the foothills of the Blue Ridge. With plenty of opportunities to indulge in spa treatments, culinary experiences, and curated activities. 500 N. Pendleton St., SalamanderResort.com

Jenn Pineau, founder of garden and flower shop Nature Composed


The illuminated Red Fox Inn & Tavern
Drink
Lost Barrel Brewing, where dogs are welcome, serves flatbreads and other small plates with craft beer, wine, and mocktails. On weekend nights, listen to live music. 36138 John Mosby Hwy., LostBarrel.com
Middleburg Common Grounds is the town’s gathering space for coffee, juices, and cocoa. The friendly eatery also serves breakfast sandwiches and pastries.
114 W. Washington St., MiddleburgCommonGrounds.com
Chrysalis Vineyard, nestled in the Bull Run Mountains in the area’s Ag District, includes a tasting room with million-dollar views that go on for miles. The notable wines feature the Norton grape, one of the first grapes to grow successfully in Virginia. 39025 John Mosby Hwy., ChrysalisWine.com
Mt. Defiance Cidery & Distillery includes two area locations. Sip cider or apple brandy around the stone hearth at the Cider Barn, just outside of town or enjoy craft cocktails and flights of spirits at The Distillery downtown. Both spots welcome food trucks on weekends. Barn: 495 E. Washington St., Distillery: 207 W. Washington St., MtDefiance.com
This article originally appeared in the December 2023 issue.