Cumberland sits in a narrow river valley in the Allegheny Mountains of western Maryland, where Wills Creek meets the North Branch of the Potomac and the ridgelines press in from all sides. It was once one of the most strategically important places in North America — the western terminus of the Chesapeake and Ohio Canal, the birthplace of the National Road (America's first federally funded highway), and a major hub for the Baltimore and Ohio Railroad. For a time in the mid-1800s, Cumberland was the second-largest city in Maryland.
That era of wealth left a legacy of handsome brick architecture, ornate churches, and a downtown — anchored by Baltimore Street — that still has real bones to it. The Queen City, as it's called, has seen better economic days, but it holds its history with some dignity. The C&O Canal towpath runs right through town, the Western Maryland Scenic Railroad still runs steam-hauled excursions through the mountains, and the Great Allegheny Passage rail trail connects Cumberland to Pittsburgh — making it a genuine destination for cyclists and hikers.
The surrounding landscape is legitimately beautiful: forested ridges, the dramatic Cumberland Narrows, winding river valleys, and a handful of state parks like Rocky Gap within easy reach. For travelers passing through on I-68, or anyone making a cycling trip on the GAP or C&O Canal, Cumberland is worth more than a fuel stop.