Homecoming: ALCO vs. FHS: First or second weekend before Thanksgiving at Greenway Ave Stadium. Homecoming is the final regular season football game for Cumberland's two public high schools Allegany High School and Fort Hill High School. The rivalry and team spirit expressed by the players and fans of each football team is unrivaled in Maryland high school football. Attendance at the game averages between 8,000 - 10,000 (approximately one-half of the population of the city.)
Tri-State Concert Series concerts throughout the year from the golden age of rock-n-roll, swing, and big-band; as well as popular country and choral music.
Western Maryland Street Rod Roundup: Over 1000 pre-1949 street rods featuring rod jousting, crafts, food, entertainment, parts vendors, vote for your favorite car. Allegany County Fairgrounds (Labor Day Weekend)
Annual Tree Lighting Ceremony and Open-House: This event centers around the annual lighting of the City Christmas Tree in the heart of Downtown Cumberland where streets filled with Cumberland Residents come to see the mayor throw the switch on the tree and participate in the sights, sounds and joy of the holiday season. During the event there are several live musical performances at prominent businesses in the city center, including holiday choral and jazz vocal performances; as well as, galleries exhibiting local artist, including ceramics, photography, metal sculpture, jewelry and water color. (first day after Thanksgiving, aka. Black Friday)
Bluegrass Jam Session: Every Sunday Evening at the Queen city Creamery from 4:00 pm to 8:00 pm or later. Free Admission.
The Great Allegany Run: Every October. 15K run from Mount Savage, Maryland to Downtown Cumberland; 5K run in Cumberland; 2-mile (3.2 km) walk on C&O Canal; and Kids' Run.
Halloween Parade: Every October along the main steen in South Cumberland.
Homecoming Parade: Every November in Downtown Cumberland.
DelFest: Annual bluegrass festival held at Allegany County Fairgrounds over Memorial Day weekend. Hosted by the Del McCoury Band.