Civil War Trails: Oakland, Maryland

Tucked into the mountains of West Maryland, in Garrett County is the picturesque town of Oakland.

There are two Civil War Trails signs in town, which are a great place to start your visit. The first sign is centrally located downtown. Begin your Oakland expedition by parking at 117 E. Liberty Street. It is hard to imagine today but on April 26th, 1863 a detachment of Confederate Captain John McNeill’s rangers stormed into town, capturing the town and the depot here. 

Begin exploring Oakland here at the B&O Railroad Museum. Image courtesy of

Today, the c. 1884 depot building hosts the B&O Railroad Museum, one of three museums located in the immediate downtown area. A host of small exhibits discusses the importance of the rail lines in this area and how John W. Garrett, president of the B&O struggled with keeping the lines open during the war. From here, turn right and walk across the green to the historic Deer Park Hotel, a brightly painted building you won’t miss. Once inside several exhibit rooms await you but we highly recommend checking out the ‘Hotels Room’ which will give you a sense of how the local lodgings accommodated travelers in the late 19th and early 20th centuries. 

Englanders traditional grill and soda fountain also doubles as an antiques store. Photo thanks to “She’s On The Go.” One of our favorite travel blogs.

After two museums you might be a bit peckish. If you are visiting Oakland during the summer you are in for a local treat. Turn right and walk up South 2nd Street, turning right again and you’ll spy ‘The Bottling Plant’ building home to local hotspot – Devler’s Ice Cream. If it’s local eats you are after head up East Alder Street and pop into ‘Englander’s Antiques, Grill and Soda Fountain.” Yup, you read that right. They have been around for decades and have all the hallmarks of a classic lunch counter and soda fountain. Retro spinning stools, buckwheat cakes, burgers, and milkshakes. It’ll be a hit with the kids, or even your battlefield buddies.

Another block further on the same side of Alder Street you’ll find the site of the c. 1859 ‘Cobblers Shop.’ While it takes some imagination to remove the modern additions to the building, it wouldn’t be surprising if McNeill’s men stopped on their raid to grab shoes, boots, and tack items in 1863. Across the road is the County Courthouse which also offers and interpretive sign. However, you’ll want to head back down towards the B&O Railroad Museum and your ride to make it out to the next site. 

Punch in 10 Spruce Lane, Oakland into your navigation device and park at the Glades Town Park. Take the walking trail as it winds its way down along the railroad tracks towards Fort Alice. In 1861, Fort Alice was constructed to guard the strategically vital railroad crossing over the Youghiogheny River here. While a Company of the 6th West Virginia Infantry tried to resist McNeill’s men closer to town, local source material suggests that the locally raised Union soldiers assigned to the Fort in April 1863 were off hunting when McNeill’s men struck. Burning the bridge, destroying portions of the Fort, McNeill’s men under the command of Col. Asher Harman effectively shut down the B&O railroad for several weeks before it could be repaired. The walk there and back will take about 45 minutes and is relatively flat and easy to traverse. 

Obviously you could spend an entire day exploring Oakland’s historic sites. However, the region is host to many attractions for everyone. Boating, skiing, biking, whitewater adventures and more. Check in with our friends at Visit Deep Creek to begin planning your trip today. 

Let us help you travel like a local. Take a look at our maps, and don’t hesitate to ask for our recommendations for good eats, drinks, and lesser known spots along the way. Follow #civilwartrails and create some history of your own.

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