Holiday Activities - December

Open for Holidays

The Best Place for Holiday Spirit...is in Your Backyard

We look forward to seeing you back in Middleburg for all of our 2023 Christmas and Holiday activities! Race into the Holidays with Middleburg, Virginia!Screen Shot 2022-11-07 at 4.08.32 PM

  • Christmas Tree Lighting - Friday, Dec. 1st at 5:30pm (doors/gates open at 5:00pm)
    • Come enjoy a community celebration of light and joy as we kick off the holidays at The Woolley Fox!
  • Christmas in Middleburg Parades - Saturday, December 2nd
    • RESERVED PARKING REQUIRED 
    • No parking is available in Town or along Route 50 - violators will be towed!
    • 11:00am - Middleburg Hunt Review
    • 2:00pm - Traditional Christmas Parade
    • Food trucks, music, shopping, and fun all day long!
  • Month-long events - HAVE A DICKENS OF A CHRISTMAS IN MIDDLEBURG!
    • December 9th - Dickens of a Dog Show
    • December 16th - Dickens of a Christmas - 10am-4pm
    • The Town turns into a scene from a Charles Dickens novel as carolers, dancers, actors, musicians, and shop owners encourage merriment and joy throughout Middleburg. Come join us for renditions of
      “A Christmas Carol” and for some wassail! 
    • South Madison Street and throughout the Town.
  • Carriage rides through historic Middleburg! 
    • Dates: November 25,26 & December 3, 9, 10, 16, 17, 23, 24, 30, 31!
    • Times: 10AM-2PM
    • Tickets go on sale Monday, November 6th!! Click here to purchase
    • Enjoy a stroll through beautiful, historic Middleburg in a horse-drawn carriage during the month of December. This unique opportunity allows you to see the Town from a different perspective. Kids love it, and so will you.

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COMPLIMENTARY HOT COCOA


Scruffys Ice Cream and Coffee Parlor Sign

Visit Scruffy's Ice Cream Parlor for a complimentary cup of hot cocoa as you stroll the streets and shops in Middleburg. Be sure to visit a local bakery or coffee shop for a pastry or slice of pie to go with it!

FREE COCOA will be available on weekends only starting on Small Business Saturday - November 25th!



Do you need a LAST MINUTE GIFT?? Check out our shops, or consider buying a Shop Middleburg gift card. It can be used at 23 locations in Town, and new businesses are being added regularly.

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