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Visit Middleburg This December for Holiday Shopping, Dining & More!
Friday, December 5 – Christmas Tree Lighting
530pm (gates open at 5pm) – Official holiday lighting at the Pink Box
Saturday, December 6 – Breakfast with Santa
Join Middleburg Community Charter School (101 N. Madison St) for a delightful morning of festive fun at the 2025 Breakfast with Santa in Middleburg! Kick off the holiday season with THE BEST (and cheapest) PARKING IN TOWN, a warm, scrumptious breakfast prepared by 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 jolly old St. Nick!
Saturday, December 6 – Christmas In Middleburg Parade
11am – Middleburg Hunt Review
2pm – Traditional Christmas Parade
Enjoy food trucks, music, shopping all day at this annual holiday tradition
No parking is available in Town or along Route 50 (towing enforced)
Saturday, December 13 – Jingle in the 'Burg
10am to 4pm – Head down to S. Madison Street to experience festive performances by carolers, dancers, actors and musicians, while shopping holiday vendors with food, drinks and spirits.
1pm – Well-behaved pups are invited to participate in the Jingle Paws Parade presented by Tilley's Pet Supplies, which starts at the National Sporting Library & Museum and runs through town, followed by a Yappy Hour at Brick & Mortar.
November 30 + December 13 & 14, 20 & 21, 27 & 28 – Carriage Rides
Nothing is more magical than getting in the holiday spirit with a horse-drawn carriage ride through the Town. Sign up your family and friends today
Click for full details and to purchase your ticket
Free Hot Cocoa!
Visit Piedmont Drip & Dip (6 W. Washington St) 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 promotion will be available on weekends only starting on Small Business Saturday - November 30th (Special offer NOT VALID on December 6th at Christmas Parade).
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