Find art, history and mystery in Cumberland

Cumberland has a rich arts and culture scene and a bounty of local boutiques, eateries and wineries while still preserving its history and granting visitors a window into its past.

EDITOR’S NOTE: The Western Mayrland Scenic Railroad’s steam train is currently not running.

A little over two hours from Northern Virginia, Cumberland, Maryland, is a historic town tucked into western Maryland foothills that saw its heydey as an industrial giant due to its significant roads, waterways and railroads connecting it to the rest of the country. Now, Cumberland has a rich arts and culture scene in its downtown area and a bounty of local boutiques, eateries and wineries while still preserving its history and granting visitors a window into its past.

Arts and shopping districts in Cumberland’s historic neighborhoods

Head to downtown Cumberland for arts, architecture and shopping. The latter can be found in the Downtown Historic District, the center of which is a brick pedestrian-only walkway on Baltimore Street. There, you’ll find antique housewares (Baltimore Collectibles, Gigi’s Attic), furniture (Elderbird Restorations), clothing and accessories (Lew Lew Belle Boutique, La Bella Vita).

On the other side of Wills Creek, you’ll find the Washington Street Historic District. All of downtown Cumberland is rich in 19th– and 20th-century architecture, including Victorian and Gothic styles, but here, you can take a look at some of the city’s standout landmarks, like the Emmanuel Episcopal Church and the Allegany County Courthouse.

In addition to shopping, the downtown area has a thriving arts district that’s home to a number of galleries and theaters on either side of the creek. The Allegany Arts Council is a major driver behind the arts in Cumberland, hosting exhibits at its Saville Gallery, regular community events, classes and Saturday Art Walks in the summer. The C. William Gilchrist Museum of the Arts contains six galleries with permanent collections, new exhibits every month and community events and performances. (The museum, housed in a 19th-century mansion with gardens, should also be included in your architectural tour of Cumberland.)

Both historic neighborhoods are outfitted with music and theater venues, too, including the New Embassy Theatre and Cumberland Theatre. And if you make your trip this summer, Cumberland hosts a farmers market and the weekly outdoor music series Cumberland Comes Alive in the nearby city center.

Narrows Bridge
Photo courtesy of City of Cumberland

History and entertainment on the Western Maryland Scenic Railroad

The Western Maryland Scenic Railroad preserves a piece of U.S. transportation history while still operating and offering passengers rides from the Western Maryland station in Cumberland into the Allegheny Mountains to Frostburg, Maryland. There are a number of round-trip travel packages available on the steam train—which debuted in the early 20th century and has since been restored—including a narrated trip through the mountains to Frostburg, offering historical context for the train and journey, and a murder mystery train ride that follows one of four interactive story lines and comes with a three-course dinner.

Maryland wines at Charis Winery downtown

Top off your trip with a stop at the highly rated Charis Winery back in downtown Cumberland. The winery serves a number of grape varietals (moscato, shiraz, barbera and more), and its tasting flights can either sample the winery’s dry to semisweet options or semisweet to sweet wines. The winery also frequently hosts live music.