Events
2024 Maryland State Banjo, Fiddle, and Mandolin Championships
The Maryland State Banjo, Fiddle, & Mandolin Championships have been an Autumn Glory tradition and a great family fun event for many years. We welcome all participants and spectators.
Autumn Glory Grand Feature Parade
The Town of Oakland and the Greater Oakland Business Association is proud to present the 57th Annual Autumn Glory Grand Feature Parade on Saturday, October 12th at 1pm. Be a part of the celebration of the fall foliage season at Garrett County's 57th Annual Autumn Glory Festival Grand Feature Parade, which will be held Saturday, October 12, 2024, in downtown Oakland, Maryland at 1:00 p.m. The title sponsor of the 57th Annual Autumn Glory Festival Grand Feature Parade is First United Bank and Trust
Southern Garrett High School Tournament of Bands
Join Southern Garrett High School Marching Band for an exciting evening as they host the Autumn Glory Tournament of Bands! Starting at 6pm, eight talented marching bands from across the region will take the field to showcase their unique styles in a spirited competition for top honors. Brenda’s Body Shop will also perform. Experience the energy and dedication of these young performers as they captivate the audience with their skill and creativity. Bring your friends and family to cheer on your favorite bands and enjoy a memorable night of music and community spirit!
Light Up Night
A Great Small Town Christmas will kick off with a Light Up Night on Friday, November 29th at the Oakland B&O Museum. The event will start with a Walking Holiday Light Parade, led by Santa Claus starting at the Town Parking Lot. All are invited to participate in the walking parade as we make our way to the B&O Museum for the official tree lighting.
Small Business Saturday
On Saturday, November 30, shop in Oakland for Small Business Saturday. Find discounts and promotions in shops all across town and visit your favorite nonprofit serving hot cocoa for the Cocoa Crawl in various businesses! Take a sleigh ride downtown and visit the Ruth Enlow Library for Story Walk.
Great Small Town Christmas
On Saturday, December 14, join us for A Great Small Town Christmas. Find discounts and promotions in shops all across town! Enjoy Soup & Santa, take a sleigh ride downtown and visit the Ruth Enlow Library for Story Walk.
Winterfest
Join us for Winter Fest on February 15, 2025 from 11 a.m. to 4 p.m. Previous years have featured kids’ activities, store specials, live music and performances, the wine walk, and ice sculptures!
Little Yough Summer Music Festival
The Remedy is a nine-piece ensemble of local musicians. For over 15 years they have been entertaining audiences in the DCL area. Their music spans decades and genres which makes them appealing to all ages. But, most importantly their energy, versatility and individual musical talents are captivating to both listen to and watch.
Little Yough Summer Music Festival
Smoke Wagon is a five man band based out of Morgantown, WV that promises to get you out of your seat as well as singing along. Their music encompasses many different genres spanning numerous decades of hits. You will hear everything from Cash, Willie and Waylon to CCR, Van Halen, ZZ Top and Tom Petty. Come out and enjoy the evening with us. They promise to play something you grew up listening to and love.
Little Yough Family Flicks
Join us at the Mountain Fresh Pavilion at 7pm - featuring Teenage Mutant Ninja Turtles Mayhem