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Christmas in Middleburg: December 2, 2023

Christmas in Middleburg: December 2, 2023

Middleburg Trots Out Their Finest for Holiday Festivities

MIDDLEBURG, VA — The historic Town of Middleburg, located in the heart of Virginia’s horse country, is well known for its bucolic countryside, unique shopping, fine dining, and luxurious accommodations. Each year on the first Saturday in December, the Town hosts its annual holiday celebration, Christmas in Middleburg. The traditional Christmas festivities, with the backdrop of a classic Hunt Country village, have become a family tradition and essential part of the spirit of Christmas for small children, world travelers, and visitors from far and wide.  

Christmas in Middleburg is a wonderful community event. Festivities begin at 8 a.m., Saturday, December 2, with Breakfast with Santa and a silent auction at the Middleburg Community Charter School. The event features a delicious breakfast, silent auction, and pictures with Santa & Mrs. Claus. Visit for additional information.

Starting at 11 a.m., the Middleburg Hunt Review takes to the streets creating a spectacular sight as approximately 150 horses, riders in hunting attire, and dozens of hounds come through the town. Throughout the day there are choir performances, as well as shopping and dining in the town’s shops and restaurants. In addition to the town’s restaurants, food trucks will be located on South Madison Street as well as North Pickering Street behind the Truist Bank during the event. King Street Oyster Bar will also have “Sip & See” tables available on South Madison Street. The “Sip & See” table option can be purchased with parking at

The Middleburg Christmas Parade begins at 2 p.m. as spectators line the sidewalks along Washington Street (Route 50) to watch as a unique assortment of floats, troops, and musical groups march by. In keeping with the animal friendliness of the town, the parade includes horses, ponies, and a variety of dog breeds. Not to be missed are the antique fire trucks and, of course, Santa bringing up the rear riding on a beautiful horse-drawn coach. The parade will be hosted by Middleburg residents Laticia Headings and Vice Mayor Peter Leonard-Morgan.

From 3 p.m. to 6 p.m. adults can relax and enjoy the Spirit of Middleburg. The progressive hospitality of food and wine tasting will allow adults to wind down and relax at Middleburg establishments of their choice while sampling foods, wines, and spirits from throughout the area at local restaurants. Visit for a full list of Spirit of Middleburg stops.

The Middleburg Business and Professional Association and the Middleburg Museum will host a Christmas Tree Lighting ceremony on Friday, December 1. Caroling begins at 5 p.m. behind The Woolley Fox at 12 North Madison Street. Refreshments will also be served. Mayor Bridge Littleton will lead the countdown to the tree lighting. The town’s Christmas tree features over 1,000 lights. Call the Middleburg Museum at 540-687-8888 for additional information.

Visitors should arrive early to avoid traffic delays and to find a perfect spot along the parade route or in the grandstand seating area located on North Madison Street. Visit to purchase parking passes. Shuttle service will be provided. Please note that advanced purchase of parking passes is required (no day-of sales). Free handicap-accessible parking will be available behind Middleburg United Methodist Church (15 West Washington Street). Space is limited. This will be the only parking option available without advance purchase. A valid DMV-issued disabled parking placard or license plate is required.

For more information, please email Visit to view an event schedule, list of activities, shop specials and more. Follow Christmas in Middleburg on Facebook for event updates. Visit calendar for a complete schedule of events taking place in Middleburg this holiday season.

Photo by Jay Hubbard.

Posted on: October 10, 2023

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