A few hours before the 11 a.m. Hunt Review, the traditional start of the Christmas in Middleburg Parade, Tara Wegdam helped her employees move crockery-laden tables to expand the aisles of Crème de la Crème, the Washington Street gift and tableware shop she owns with her husband Ben. “The parade brings thousands of people to town,” Wegdam explains. “We get so many people coming in dressed in big winter coats, we don’t want them bumping into each other or anything else.” When she heard the parade had begun, she went outside to watch the Middleburg Hunt, resplendent in their crimson and black coats, trotting down Washington Street under a crisp, blue winter sky.

In front of the riders came the hounds. One broke away from the pack and turned toward Wegdam. She felt a woosh of chilly December air, and by the time she saw the brown and white tail disappear through her open front door, the other 35 hounds had also rushed through on either side of her. She reached the shop’s front door and saw the interior had literally gone to the dogs. “They went everywhere, around every table, up and down every aisle. Then they came out and were back on Washington Street before I could say a word. They didn’t break a thing,” she recalls. Then she saw a pastoral painting that had been propped up against one table. It had slid to the floor in the commotion and in the center of the picture was one big, dark pawprint. “[It] sold almost immediately because the person who bought it couldn’t believe what had just happened and thought it was hilarious — what better souvenir for the day,” Wegdam remembers.

For Wegdam, the entire experience was magical. “There are other Christmas parades in other places, but nothing like this. Ours is really, really special.” Current co-organizer Michelle Myers offers another word to describe the parade: Unlimited!

“Last year we had to limit everything because of COVID-19. This year everyone is contributing,
everyone is part of it,” Myers says. This year, the parade will include — for the first time ever — a marching reunion of at least 10 members of Middleburg’s undefeated 1971 Little League team, most of whom haven’t seen each other in 50 years.

From dawn to dusk on Saturday, December 3, Route 50 and Washington Street will be closed to automobiles to make room for as many as 20,000 spectators. Parking for participants and spectators will be confined to intercept lots along the outskirts of town (see ChristmasinMiddleburg. org for more details). Most restaurants in town will be open during the parade’s midday pause to serve lunch. They will be supplemented by food trucks.

Jim Herbert, a commercial realtor who has helped organize the parade as far back as 1979, calls it “a genuine celebration of love and the Christmas message. It is also the best time of the year to show people what the Middleburg community is all about.”

He ticks off the statistics: A mile and a half long, beginning with the Middleburg Hunt (and their hounds!) and ending with Santa Claus on a horse-drawn carriage, lasting over an hour and a half (with a break in the middle for lunch) with spectators lining Washington Street “in every kind of weather,” including the blizzard of 2009.

“We all met at 6 a.m. when we heard that snow was expected. There was talk of canceling the parade, and if we had known what we were getting into, we probably would have,” Herbert says. But they didn’t.

Photo by Nancy Kleck.

The snow came down just as the hounds hit Washington Street, and photographers snapped what Herbert calls the “iconic” shots of the parade: the hounds leaping before 140 riders in bright red and black jackets peppered with big flakes that would soon fill the region in nearly nine inches of snow.

Penny Denegre, joint-master of the Middleburg Hunt, also has fond memories of the blizzard. “We have concerns when the weather gets very cold, but that time, and every other time the weather seems to be against us in Middleburg, it was magical.”

The Middleburg Christmas Parade is one of the hunt’s most important yearly activities, one that emphasizes the town’s unique relationship with Hunt Country and the traditions that go all the way back to Virginia’s colonial history. It is one of the only times when people who don’t hunt can watch the hounds and riders that do. And the horses know it. “We don’t have spectators normally. On the parade morning, the horses are always a little concerned when there is something out of the ordinary,” Denegre shares.

But when they round the corner at the top of the hill and the hounds take off, “it becomes this lovely outpouring of warmth.” When the parade resumes at 2 p.m., few groups are as highly anticipated as the thirty Middleburg Charros who demonstrate Mexican rope wrangling and rodeo skills that, according
to Charro rider Juliana Ortiz, have been passed down through her extended family for generations. “What we do is rarely seen in the east,” says Ortiz, who, when not teaching horses how to dance, is an accountant. “The decoration, the dances, the roping, and the salutes are all part of our heritage, so it is important for us to be in the parade and show everyone how exciting and magical it can be.”

New for this year will be even more of Ortiz’s cousins standing on horseback, jumping through ropes. “It started last year with one or two [of us] having some fun. Now everybody wants to do it!” she says.

The more than 100 corgis that follow are always a huge hit with children “because they are incredibly cute!” says Holly Hudimac, who will be joined by her dogs Abby and Panda. “This is hysterical and a lot of fun and the children love the dogs because they’re small and adorable. Where else are you going to see so many corgis in one place?”

Competing in cuteness will be the 70 children, ages 4 to 8, from The Hill School, dressed as elves and gift-wrapped presents. Having decorated the front windows of the Washington Street Safeway Supermarket during the previous week, some ride on The Hill School’s float. First grader Adelaide Hottel enjoys the float “because I get to ride with my friends, and we see a lot of people.”

“When I first saw the parade ten years ago, it was pretty spectacular. Of all the nice things you can do in Middleburg, it’s just wonderful to watch the town literally celebrate itself in the warmest, funniest, kindest way. To be part of this, even if it’s just to keep track of the kids and wave at the people, it’s pure joy,” shares Kelly Johnson, the school’s enrollment director.

The pure, distinctively snorting growl of thirty motorcycles decorated with antlers and flashing holiday lights, all ridden by members of the Winchester Harley Owners Group, is music to the ears of club president and Winchester motorcycle dealer Barbara Grove. “I prefer to watch from the sidelines and let the others get the glory,” says Grove, who is hoping to snag a table at the Red Horse Tavern, where, on any other weekend, bikers hailing from every point on the compass tend to congregate. “We love that ride to Middleburg so much that around fifteen years ago, we decided to help out,” Groves explains. For the past two months, members of the biker group have brought food on their rides from Winchester and given it to Seven Loaves food pantry. This year alone, the Harley Group has donated well over 1,000 pounds of food. “Canned goods, turkeys, whatever might be appreciated,” Grove adds. “We may not live here, but Middleburg makes us feel at home.”

Weaving in and out of the parade you are likely to spy Suzanne Obetz, the executive director of the Middleburg Museum, in her “emergency Mrs. Claus” suit. In addition to presiding over the town’s tree lighting ceremony (at 5 p.m. on the Friday before the parade) and handling any and all letters to Santa children may leave at the museum, Obetz is one of more than 100 volunteers who will “basically do whatever is needed to be done.” She adds, “You’d be surprised how often a child’s happiness, or the fate of the entire parade itself, can depend on a needle and thread, scissors, or, heaven forbid, a Band-Aid.”

The parade typically ends with Santa who bears an astonishing resemblance to Lost Barrel Brewery’s tap room manager, Bobby Martz. “It gives me an opportunity to see the magic on everyone’s face,” he says. “The holiday is all about magic, bringing back those nice childhood memories when everything happened to make you warm, and happy to be with family and friends. What better place to celebrate than Middleburg!” Mr. Claus likes Middleburg so much that he promises to visit Lost Barrel on Saturday afternoons following the parade, where, in addition to being available for photos, he will serve a range of non-alcoholic drinks and snacks for kids. When asked how he intends to slip up and down Middleburg’s numerous chimneys on Christmas, he simply responds: “It’s magic!”

This story first appeared in the December 2022 issue.