- List of Festivals and Events in Cumberland, MD-WV
* [http://www.heritagedaysfestival.com Heritage Day Festival] , Washington St. (Mid June)
* "Farmer's Market", every Saturday downtown (From June to November)
* [http://www.alleganyartscouncil.org/static.php?page=121 Sunday in the Park] : free concerts every Sunday evening in Constitution Park Amphitheater in South Cumberland, sponsored by the
Allegany Arts Council . (From May to September)* "CanalFest", located at Canel Place (Mid July)
* [http://www.alleganycofair.org Allegany County Fair and Expo] (Mid July)
* "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 schoolsAllegany High School andFort 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)
* [http://www.avalon-resort.com/musicfest.html Avalon's Annual Music and Arts Festival] a 3 day music festival featuring Country, Folk, Blues, Rock, Appalachian, and Bluegrass music. Every August.
* "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 afterThanksgiving , 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 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.
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