Holiday Activities - December

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

We look forward to seeing you back in Middleburg for all of our 2025 Christmas and Holiday activities! 

• Christmas Tree Lighting- Friday, Dec. 5th 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 Pink Box!
• Breakfast with Santa at MCCS
  • Join Middleburg Community Charter School for a delightful morning of festive fun at the 2025 Breakfast with Santa in Middleburg! Get ready to kick off the holiday season with THE BEST (and cheapest) PARKING IN TOWN, a warm, scrumptious breakfast prepared by the inimitable Tutti Perricone of Back Street Catering, hot cocoa and coffee bar, incredible prizes in our pick-a-prize rooms, and a visit and photo ops with the one and only Santa Claus himself. Click here to purchase tickets now!
• Christmas in Middleburg Parades - Saturday, December 6th
  • 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 - JINGLE IN THE BURG!
  •  "Jingle in the Burg on S. Madison St." - 10am-4pm - Saturday, December 13th
  • The Town turns into a Hallmark Christmas movie 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.
  •  Jingle Paws Parade - Date TBD
    • Join us walking down Washington Street from the National Sporting Library and Museum to Brick and Mortar on South Madison Street.
    • Dress up your dog and have a wonderful time with your furry friends!
• Carriage rides through historic Middleburg! 
  • Dates: TBD
  • Times: 10AM-2PM
  • Tickets go on sale Friday, November 15th!! 
  • 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

Visit Piedmont Drip & Dip 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 30th (with the exception of parade day on December 6th).