In far-western Maryland, Oakland is known for its Amish farms, mountain scenery and several sights related to the past, such as the Garrett County Historical Museum, the 1884 B&O Railroad Station (one of the country's oldest) and St. Matthews Episcopal Church. The latter is also known as the Church of the Presidents, because it has been attended by several U.S. chief executives, including Presidents Cleveland, Harrison, Garfield and Grant, all of whom vacationed in the area.

Approximately 11 mi/18 km from town (near Cranes and White Trap Run Road) is the Cranesville Sub-Arctic Swamp, with an unusual exhibit of flora that's found primarily in the Arctic. North of Oakland are several scenic mountain parks that offer a host of outdoor activities. Deep Creek Lake State Park is popular for boating and watersports in summer and snowmobiling in winter, and the Youghiogheny and Savage Rivers attract white-water rafters to their rocky gorges.

Also in the area is Wisp, Maryland's only downhill ski resort, which also offers snowtubing, as well as golf and mountain biking when there's no snow.

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