A Great Small Town Christmas

Saturday, December 12, 2026 · Downtown Oakland, Maryland

Bring the family downtown for A Great Small Town Christmas! Visit with Santa, warm up at a hot cocoa stop, and browse the Bakers Market in the Arts & Entertainment District. Then find a spot to watch the Christmas parade and stay for caroling and the community tree lighting right after the parade.

What’s happening downtown

• Santa visits and letters to Santa — Bring your wish list and write a letter to Santa.

• Christmas stories and holiday crafts — Enjoy a story and make something festive to take home.

• Hot cocoa stops and holiday shopping — Sip some cocoa while you explore Oakland’s downtown shops.

• Bakers Market — Stop by the Arts & Entertainment District for holiday treats.

• Christmas parade and tree lighting — Cheer on the parade, then gather with friends and neighbors to light the community Christmas tree.

Help decorate Oakland for Christmas

Town of Oakland residents are invited to enter the Christmas Light Decorating Contest, and Oakland businesses can join the Business Window Decorating Contest. Watch for entry details and deadlines.

Save the date! We’ll update this page with activity times, locations, and parade details as they’re confirmed.

Questions or interested in sponsoring? Contact Tracy Park, Main Street Manager, at [email protected] or 240-321-3160.