Annual & Weekly Events

The next Oakland A&E CLUB NIGHT is August 24, 2019. It’s a celebration of the 1984 hit TV series MIAMI VICE. Costume is encouraged! Details are in the making.

Oakland is host to many festivals and celebrations. We're working toward gathering info and highlighting all of them on this page. Thanks for your patience!

Autumn Glory Festival

Autumn Glory Festival

The annual Autumn Glory Festival is a five-day celebration of autumn that celebrates the beauty of the local fall foliage. From Wednesday through Sunday, the area offers a wide variety of things to do indoors or outdoors. The Festival includes a feature parade on Saturday, concerts, band competitions, art exhibits, antique & craft shows and much more! 888-387-5237


Wonderful Wednesdays & Super Saturdays

Wonderful Wednesdays in Oakland, MD offers store specials, the Mountain Fresh Farmer Market, carriage rides, story hour at the Oakland B&O Museum and much more!!!
The Mountain Fresh Farmer's Market is every Saturday and Wednesday from 10am-1pm at the Mountain Fresh Pavilion on Town Park Lane. June 3-October 28. 


Little Yough Music Festival

Begun in 1966, this showcase of singer/songwriters has provided Garrett County, her neighbors and visitors opportunities to hear a variety of musical styles under the summer skies. Concerts are held every Friday evening July 7-September 1 at the Mountain Fresh Pavilion on Town Park Lane. Concerts are free, however donations are appreciated. Food is available for purchase. 


Pocket Park Movies

Pocket Park Movies are a great family night out! Pocket Park movies are shown at dusk in the Mountain Fresh Pavilion down by the Town Parking lot. Movies are shown rain or shine. Movies are shown every Thursday June 15-August 17.

Annual Car Shows

Mountaintop Cruisers

16TH Annual Autumn Glory Car, Truck & Tractor Show in the streets of downtown Oakland, Maryland Sunday, October 14th, 2018. Roll-in registration is from 9:00 A. M. till 1:00 P. M. Registration fee is $10.00.
Wall plaques will be given to the first 200 vehicles registered. T-shirts will be given as long as they last. We will have 50/50 drawings, door prizes every ½ hr., silent auction, $250.00 give away, and tires give away.
50/60/70s music after 12:00 noon.
More Info. Call Jim Bennett: 301-334-8130 or Kenny Easton : 301-334-6592