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The easiest and most accessible way to travel to and around Cumberland is by car. Main thoroughfares coming into Cumberland are US 220, US 40, Interstate 68, MD 36, and WV 28. Amtrak's Capitol Limited line also arrives at the station in downtown Cumberland twice daily: eastbound towards Washington, DC in the morning; and westbound, towards Chicago in the evening.

Walking is not only the best method, but also the only method for exploring the downtown area. The Baltimore Street commercial district is closed to traffic and is a pedestrian-only mall. Within a few blocks of this area, one can easily walk to the Canal Place Heritage Area, the Western Maryland Scenic Railroad, the Washington Street Historic District, as well as a variety of other shops and restaurants. It is important to note that while it is possible to walk from the train station to the only downtown hotel, the Holiday Inn, one has to cross a high-traffic section of railroad tracks to access the hotel as well as the rest of the downtown area.

In order to explore the rest of the city and region, however, having a car is advised. Be aware that in the downtown area, parking can sometimes be difficult to find. Two public parking garages are available: the Center City Garage on the corner of Pershing and George Streets, and the other can be entered on Liberty or Frederick Streets. There is also visitor parking at the Western Maryland Station on Mechanic street, and metered parking under the Crosstown Bridge (I-68), and along many side streets.

Country Club Mall is the only indoor shopping mall in at least a 70 mile radius of Cumberland. It is located in suburban LaVale, which is about 5 minutes driving time from downtown. Anchor stores include JCPenney, Sears, The Bon-Ton, and Wal-Mart Supercenter.

  • Baltimore Street and its cross streets have several boutiques and specialty stores of interest, including Monkey Business (trendy ladies clothing), The Book Center (quality books for all ages, as well as a wide selection of magazines, newspapers and cigars), the Emporium (independent vendors of antiques, art and collectables), and the Art Department (fine art supplies, prints, framing and matting, etc.)

Most dining in the city itself is conveniently located in the downtown area. Ethnic restaurants (Chinese) and American cuisine are widely available. Be aware that most restaurants on the downtown mall can be pricey, especially for dinner. For the more budget-conscious traveler, five fast food establishments are also located close to downtown, and the Culinary Cafe, a unique educational restaurant for students at Allegany College of Maryland, is also not costly, and is located on the downtown mall. Many other common chain restaurants are located in LaVale.

Many pubs and bars are located downtown and throughout the city. However, for the family and those who prefer non-alcoholic beverages, try Mark's Daily Grind or the Queen City Creamery for coffee.