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Christmas In Middleburg: A Tradition Like No Other

By Peyton Tochterman


One of the most popular attractions are the mounted Charros in full regalia.

Since 1979, at 10:59 a.m. on the first Saturday of the last month of the year, nearly 100 horses and riders accompanied by many howling hounds pass the Middleburg Library, turn left on Washington Street, and proceed to the crest of the hill.

The first rider from the Middleburg Hunt, dressed in traditional scarlet attire, leads a mile-and-a-half procession down into an appreciative crowd of thousands lining the streets to witness and be part of this small-town tradition.

To the local community, seeing the Hunt Review, established in 1908 and scheduled this year on Dec. 3, pass through the town's Federal Style buildings, inns, shops, and antique street lamps decorated with Christmas signs designed by former Hill School art teacher, the late Emily Sharp, Christmas in Middleburg has begun.


"Christmas in Middleburg exemplifies our spirit of community, friendship, and that small-town feeling,” said Middleburg Mayor Bridge Littleton. “It's the biggest event every year where anybody can come and experience that unique element that makes our town so special.”

Following the morning Hunt Review comes the afternoon Christmas parade. The lineup consists of local high school marching bands, over 80 floats, local fire and rescue trucks, antique cars, dog breeders, Charro cowboys, motorcycle clubs, book groups, children from local schools, and of course, Ayrshire Farm hauling Santa Claus on a horse-drawn carriage at the end.

Most of the floats are staged locally on the Hill campus. Kelly Johnson, the school’s director of enrollment, sees the annual event as another opportunity to give back to the community.

"In 1990-91, the Clark family generously donated The Hill School land, and with that gift, we want to continue in the spirit of giving,” she said. “We’re happy to play a role in the town's largest event of the year by having so many floats staged on campus.”

Planning for the parade begins almost immediately with the new year.

"We sit down with reps from the town of Middleburg and with A.J. (Panebianco, Chief of Police) to revisit the previous year's parade while it's still fresh," said Michelle Myers, who, along with her husband Doug, are the lead organizers.

"We're brainstorming about strategic planning year-round,” Doug said. “But the lion's share of the work begins in July.”

The Myers took over from former organizer Jim Herbert after meeting him four years ago.

“I couldn't believe Jim was doing all the work by himself, so we volunteered,” Dug added. “Not long after that, Jim stepped aside, and we jumped in. We were new to town, having moved to Bluemont from Ashburn, and we’re fortunate to be part of this remarkable tradition…Our long-term goal is to help local charities, through the proceeds of the parade, give back to this wonderful community."

Penny Denegre, Joint Master of the participating Middleburg Hunt, also is eagerly awaiting the 2022 parade.

"I see it as an opportunity to give back to a community that has been so supportive of the Middleburg Hunt for so long,” she said of an event many local residents call their favorite of the year.

And so, On Dec. 3, at 10:59 a.m., when the hounds come over the hill, in that highly anticipated moment, everyone in attendance will feel what Middleburg has always been, what Middleburg is, and hopefully what this picturesque Virginia village will continue to be – a tip of the cap to small town life and tradition.

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