On Friday, October 10, from 11 AM – 4 PM, Downtown Oakland kicks off the Fall celebrations with games, prizes, delicious food, and rows of local vendors. This family-friendly street festival is the perfect start to an unforgettable Autumn Glory weekend.
Explore FallFest in Oakland with friends and family, discover unique treasures, and soak up the cozy, small-town charm that makes Garrett County special. Downtown’s shops will be open and ready to welcome you—The Gallery Shop (local art and handmade goods), The Bookmark’t (books, gifts, and more), The Painted Cupboard (home décor with a vintage touch), Oakland Mercantile (a trove of curiosities), Smoke N Mirrors Photography, Flipside Sound (record shop), Bougie Bottoms (clothing boutique)—plus many more! From handmade crafts to tasty treats, every stop you make supports the neighbors and businesses that keep our community vibrant.
The Garrett County Historical Society, Transportation Museum and B&O Railroad are great stops for history buffs, and enjoy food and drinks at Black Hawk Coffee, 206 Bistro & Bar, The Green Room and Tomanetti’s Italian Eatery.
And that’s not all—the Mountain Fresh Farmer’s Market will also be open Thursday through Saturday from 9 AM – 4 PM at the Oakland Town Parking Lot. It’s the perfect spot to pick up fresh produce, baked goods, and locally made treats while you’re in town.
The fun continues all weekend long as you wrap up a fantastic Friday at the 2025 Maryland State Banjo, Fiddle, and Mandolin Championships at Southern High School from 6pm – 9pm.On Saturday head to Green Street for a feast of flavors from local food trucks, then grab a spot along the parade route for the Grand Feature Parade, a highlight of the Autumn Glory Festival. At 6pm at Southern High School the Tournament of Bands will kick off, and you surely will not want to miss it!Take a Sunday stroll through town and enjoy the Autumn Glory Car Show, where classic cars and shiny showpieces line the streets.
This year, the Garrett County Arts Council (GCAC) is introducing a few creative additions to the festivities:
Doormat Painting Workshop – Roll up your sleeves and paint your own autumn-inspired doormat! A little creativity, a splash of color, and you’ll have the perfect welcome mat for the season. Friday October 10 from 1pm – 3pm. $20 to participate, seats limited.
ARTOBER “I Spy” Challenge – A week long quest for all ages during Autumn Glory! From October 6 through to the 10, keep your eyes open for everyday magic (or create some of your own!). From “something golden” to “a moment of joy,” the prompts invite you to spot (or create!) little sparks of creativity wherever you go. Share your finds with #GCARTOBER and challenge friends and family to join the adventure!
Garrett Arts Passport Launch – Autumn Glory also marks the launch of this year’s Garrett Arts Passport, a program made possible by the Mountain Maryland Gateway to the West Heritage Area. The Passport is your guide to exploring creative gems across the county, and remembering arts and cultural festivals that take place throughout the year! Collect stamps as you go and discover how many artistic stops you can check off the list! Previous editions have taken participants from Oakland’s Arts & Entertainment District to the hills of Grantsville and beyond—and this year’s Passport promises even more discoveries waiting just around the corner- maybe even closer than you think.
Grab your sweater, gather your crew, and head downtown for a weekend full of pumpkins, laughter, and autumn spirit. Oakland’s FallFest and Autumn Glory are more than just a festival—they’re a celebration of community, creativity, and the joy of shopping small while making big memories.
For more info, visit garrettarts.org or follow GCAC on Facebook and Instagram @garrettcountyartscouncil.
Written by Rachel Precht.