Oakland kicks off the Holidays with Small Business Saturday & Christmas Giveaway

Published 8:01 pm Thursday, November 20, 2025

Oakland is about to flip on the full holiday spirit, and the Chamber of Commerce is inviting everyone to join in the fun while supporting the businesses that keep the town thriving.

Small Business Saturday returns on Saturday, November 29, and local shops are gearing up to welcome neighbors, families, and out-of-town guests ready to get a jump on Christmas shopping.

From festive window displays to the familiar faces behind the counter, downtown Oakland will have that cozy “Hallmark town” feel—twinkling lights, good conversations, and the satisfaction of knowing every dollar spent helps keep the hometown strong.

But the excitement doesn’t stop there.

Beginning November 29 and running through December 23, shoppers have a chance to turn their holiday spending into cold, hard Christmas cash. For every $50 spent at participating Oakland businesses, customers will be entered into the Chamber’s annual Christmas Giveaway, a drawing with some impressive prizes:

Grand Prize: $500

2nd Prize: $250

3rd Prize: $100

Stores will be offering double punches on purchases on November 29th, making it a perfect time to check items off your gift list while stacking your rewards.

Winners will be drawn and announced on Christmas Eve, adding a little extra sparkle to someone’s holiday.

The Chamber hopes the month-long promotion encourages folks to keep their shopping local, reminding everyone that the strongest holiday seasons are the ones we build together.

Shopping small isn’t just about gifts under the tree—it’s about supporting the friends, families, and neighbors who pour their hearts into their businesses all year long.

So bundle up, grab a cup of cocoa, and make your way downtown on November 29. Oakland’s merchants are ready to welcome you, celebrate with you, and help make this Christmas season one to remember.