Get out the lights and give your neighbors something to smile about! Main Street Oakland invites Town of Oakland residents to enter the 2026 Christmas Light Decorating Contest as part of A Great Small Town Christmas.
Whether you love classic white lights or a yard full of color, we’d love to see what you create. Cash prizes will be awarded to first-, second-, and third-place winners.
How to enter
Entry is free and open to residents with a display address within the Town of Oakland, Maryland. Register by Sunday, November 29 with your name, contact information, and display address. Main Street Oakland will share the registration link soon. No Microsoft account or sign-in is needed to register.
Contest rules
Have your outdoor display ready and visible from the street by Friday, December 4.
Turn your lights on after dusk each evening from December 8 through 10 so judges and voting community members can see your display.
Judges will score displays on overall appearance, creativity, Christmas theme, and use of lights. The higher creativity score breaks a tie. If a tie remains, the judges will decide together.
If a public viewing map is offered, your display address will be included only with your permission.
Vote for your favorite display
Community members can vote by scanning the contest QR code or visiting the Town of Oakland website. We’ll share voting dates and the voting link closer to the contest.
We’ll announce the winners at the tree lighting after the Christmas parade on Saturday, December 12, in downtown Oakland.