Visit Downtown Oakland

As the county seat for Garrett County, the town of Oakland features many different small businesses like antique shops, museums, restaurants, and activities for the whole family. The historic Oakland, Maryland is located just 8 miles south of Will O' The Wisp.

Museums in Downtown Oakland

Planning a trip into Oakland, is one of our top things to do in the Deep Creek area. Once you arrive in downtown Oakland, you will be welcomed by that small town feel full of local businesses, restaurants, farmers markets, and popular festivals. In October, the town hosts its annual Autumn Glory festival. This is a 5 day event that celebrates the beauty of the surrounding fall foliage with parades, craft shows, and art exhibits. This is an event you don't want to miss!


During the summer, you can stop by the farmers market for fresh produce, baked goods, and local flowers. In the winter, Oakland also hosts a Winterfest. This popular festival takes place every February, and you can go for a sleigh ride around town, view ice carvings, sample local wine, and listen to outdoor music.


Oakland also has great museums and antique shops around town. Dig through the history of Garrett County and you will be sure to find some hidden treasures. The Oakland B&O Museum, the Garrett County Historical Museum, and the Transportation Museum each highlight different areas that make Garrett County, MD so great.


Even though Oakland has many small businesses to give you that small town feel, there are also other larger retail chains located along the drive from Will O' The Wisp to Oakland. If you are interested in learning more about the historic area of downtown Oakland, you can visit their website here.


See more Things To Do.

Autumn Glory Parade, Oakland, MD
Museum in Oakland, MD
Railroad Museum in Oakland, MD
Fall Drone Shot of Will O' The Wisp