How Christmas in Middleburg Became a Holiday Legacy
Story by Shayda Windle
The Christmas in Middleburg Parade, like many traditions rooted in Hunt Country, has a charming and storied past. It’s been said that the first parade began sometime in the 1970s, when a small group of friends and founding members — Punkin Lee, Tyler Gore Sr., Patty Arwine, and Cissy Bunn — set out to create an event that would bring the community together.
The spirit lives on through the traditions still celebrated each year. From the beginning, Christmas in Middleburg has been and remains a reflection of the Middleburg community and what makes it so special: the horses and hounds, local businesses, and the people who call this place home.
Over time, the parade has evolved from a small local gathering into a regional attraction. Carmen Arwine explains, “In recent years, the county and surrounding areas have experienced significant growth. With that, the parade and town have gained a lot of attention. As family and friends from near and far share their experiences, the Christmas in Middleburg Parade has become a family tradition for many people.”
Widespread attention to the town’s unique equestrian-themed holiday traditions were further amplified by Willard H. Scott Jr., beloved weatherman on NBC’s Today Show for more than 30 years, when he mentioned Christmas in Middleburg on national television, drawing prevalent notice of the town.
Since then, the Christmas in Middleburg Parade has been featured in numerous outlets and was recently recognized by Condé Nast Traveler as one of the best U.S. destinations for Christmas, cementing its place as a Christmas tradition far beyond Loudoun County.
What many people may not realize is that Christmas in Middleburg is a nonprofit organization, formally established in 2010. The organization coordinates and manages both the Hunt & Hounds Parade, featuring the Middleburg Hunt, as well as the Community Parade.
The board, led by Doug Myers, also coordinates parade logistics with The Hill School, secures sponsorships, and collaborates with town team members. Funds raised through paid parking help cover essential expenses, including shuttle transportation, safety barricades, and visitor amenities. This year, the board introduced the Kid Zone, located at the Middleburg Community Center; hosted the Pickwick Singers at Emmanuel Episcopal Church; and collected donations for Seven Loaves food pantry.
Foxcroft School students brought the Kid Zone to life between the two parades with creative activities, games, face painting, and a puppet show — offered for free thanks to local sponsors and residents.
Special thanks are extended to the Town of Middleburg as well as the countless volunteers, residents, and local businesses who contribute their time, patience, and energy each year to make the event possible.
“This community celebration would not be possible without the generous support of the Middleburg Police Department, our volunteers, and sponsors,” Myers and Arwine say. “We are deeply grateful to every organization and individual who invests in making this event a success.”
For more information on how to support Christmas in Middleburg, visit christmasinmiddleburg.org.
Featured photo courtesy of Christmas in Middleburg.
Posted on: January 6, 2026