12/12/2025 to 12/13/2025
Get DirectionsCelebrate the holiday season in the heart of downtown Oakland during A Great Small Town Christmas! This two-day celebration brings festive fun for the whole family with sleigh and carriage rides, visits with Santa, shopping and dining specials, and the town’s annual tree lighting ceremony.
On Saturday, December 14, the celebration continues with Soup & Santa, sleigh rides through downtown, and the Story Walk at the Ruth Enlow Library. Local shops will be offering discounts and special promotions throughout town, making it the perfect time to finish your holiday shopping while enjoying small-town charm.
- When: December 12–14, 2025
- Where: Downtown Oakland, MD
- Tickets/Admission Cost: Free admission
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Frequently Asked Questions: A Great Small Town Christmas
What activities are included?
Guests can enjoy sleigh rides, photos with Santa, Soup & Santa, shopping promotions, and a Story Walk at the Ruth Enlow Library.
Do I need to purchase tickets?
No, the event is free and open to the public.
Where should I park?
Parking is available throughout downtown Oakland, with some streets temporarily closed for event activities.