Grace & Matthew

December 7, 2024 • Leesburg, VA, USA

Grace & Matthew

December 7, 2024 • Leesburg, VA, USA

Christmas in Middleburg

Picture of Christmas in Middleburg
Downtown Middleburg, VA

We suggest you spend Saturday morning and afternoon in downtown Middleburg.


Grace was a campus tour guide at the College of Charleston and she appreciates history, so here is a brief but important history lesson on the town :)


Middleburg has a rich history that dates back to 1728 when a man named Joseph Chinn, who was the cousin of George Washington, established a fieldstone tavern on an old Native American trail. This tavern eventually became known as the Red Fox Inn and is one of the oldest continuously operating inns in Virginia and the United States. The Red Fox Inn is hard to miss when visiting the town, and it is open for guests to stay at, check out for lunch, or enjoy beverage at the bar (to stay hydrated before the wedding, of course).


The day of our wedding also happens to be one of its largest yearly events, Christmas in Middleburg. Please see below for a description of the event. Matt and I have made so many wonderful memories in Middleburg and we hope you guys will too!


Christmas in Middleburg:

"Saturday is a full day of family festival activities, where the community comes together, celebrates a spiritually moving holy season, and individuates itself eccentrically and endearingly in doing so. The day begins with Breakfast with Santa and is followed by an iconic Middleburg Hunt review with riders on horseback and a pack of hounds coming down the main street.


After lunch, the Christmas Parade begins, featuring foot beagle hunt clubs, polo clubs, animal affinity groups (corgi owners, Great Pyrenees owners, llama and alpaca owners, etc.), community groups (VFDs, schools, scouts, churches, clubs), enthusiasts groups (MG cars, old fire trucks, Mini Coopers, muscle cars), business floats, reenactment bands (Civil War, Revolutionary War, Scots highlands), high school bands, and Santa on his coach drawn by matched Ayrshires closing the parade.


All day long there are special events including:

Breakfast with Santa and a silent auction at Middleburg Community Charter School


A greens show at Emmanuel Episcopal Church parish hall

Children’s activities throughout town


11:00 am Middleburg Hunt Review, horses and hounds down main street


2:00 pm Christmas Parade

Food and drink indoors and out


A progressive wine crawl and more!


In the past, thousands of visitors from across the greater Washington DC area attended the many activities and events, lining our closed streets for “Holiday Seasoning” in the countryside."

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