There is a moment each year when Oakland seems to glow from the inside out, when storefronts sparkle, familiar faces return, and the cold mountain air feels just a little warmer. The holidays have always suited our small town, and this year’s celebrations promise all the charm, creativity, and cheer that make winter here feel truly special.
The season begins on Friday, November 28, when Light Up Night transforms downtown into a snowy storybook scene. Santa leads the parade straight to the tree lighting at 6 PM, filling the evening with the kind of wonder that makes even grown-ups pause. Hot cocoa, cookies, and treat bags bring sweetness to the night while sleigh rides jingle through the streets. Keep an eye out for a few familiar holiday characters; the Grinch, Olaf, and Buddy the Elf have all promised to stop by and stir up a little mischief and joy.
As dawn breaks over the mountains, Small Business Saturday invites neighbors and visitors to wander through downtown, discovering treasures in every locally owned shop. When you choose to shop small, your dollars ripple outward, supporting local families, sustaining artists, and strengthening our creative economy. For gifts that are heartfelt, handmade, and uniquely Garrett County, visit The Gallery Shop, open Monday through Saturday from 10 AM to 5 PM. Every piece comes from a regional artist, so you will find something infused with meaning, imagination, and community spirit.
The festivities continue on Saturday, December 13, when A Great Small Town Christmas brings downtown Oakland to life from 11 AM to 4 PM. Sleigh rides return from noon to three. Santa once again holds court for eager children, and a holiday photo booth and bakers, and makers market brighten the day from 10 AM to 4 PM.
Throughout town, local nonprofits will be serving warm, hearty soups, each cup a small act of comfort and generosity. This year’s soup stations include the Southern Garrett Marching Band with gift wrapping, the Southern Garrett High School Theatre Department with face painting, Bridging Gaps, Garrett County Lighthouse at Archway Station, the Garrett County Arts Council, Order of the Eastern Star, Marine Corps Toys for Tots, Garrett County NAACP and Garrett Forward, AAUW Garrett Branch, and Southern Garrett High School UNICEF.
Donations are welcome and directly support the work these organizations do all year long.
Children are encouraged to bring their letters for Santa and slip them into his special mailbox. Be sure to add your name and wish list so the elves can get to work. In a world that moves quickly, the holidays in Oakland invite us to slow down, savor small moments, and reconnect with what matters most.
May your season be filled with wonder, warm bowls of soup, and the simple joy of a town that celebrates together.
Written by Garrett County Arts Council