Events in Cumberland, Maryland

25 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.

What's coming up

• Downtown Cumberland Farmers Market
  Thu 6 Aug 2026, 9:30 AM — Market
  Downtown Cumberland Farmers Market (Baltimore Street) · 113 Baltimore St, Cumberland, MD 21502 · Free entry
• Standup Comedy at Dig Deep Brewing! (Cumberland, MD)
  Sat 19 Sep 2026, 8:00 PM — Comedy
  Dig Deep Brewing Co. · 2 Howard Street #Suite B, Cumberland, MD 21502
• Crabs for a Cause 2026
  Sat 26 Sep 2026, 1:00 PM — Meetup
  Cumberland Outdoor Club · 31 Thomas St, Cumberland, MD 21502 · $49.87 · 21+
• The Pillowman
  Thu 8 Oct 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502 · 18+
• The Pillowman
  Fri 9 Oct 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502 · 18+
• The Pillowman
  Sat 10 Oct 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502 · 18+
• The Pillowman
  Sun 11 Oct 2026, 2:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502 · 18+
• The Pillowman
  Fri 16 Oct 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502 · 18+
• Punktober Fest 2026
  Sat 17 Oct 2026, 4:00 PM — Festival
  MEZZOS · 114 South Centre Street, Cumberland, MD 21502
• The Pillowman
  Sat 17 Oct 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502 · 18+
• The Pillowman
  Sun 18 Oct 2026, 2:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502 · 18+
• The Pillowman
  Fri 23 Oct 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502 · 18+
• The Pillowman
  Sat 24 Oct 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502 · 18+
• Dr. Seuss' How the Grinch Stole Christmas
  Thu 3 Dec 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Fri 4 Dec 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Sat 5 Dec 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Sun 6 Dec 2026, 2:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Thu 10 Dec 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Fri 11 Dec 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Sat 12 Dec 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Sun 13 Dec 2026, 2:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Thu 17 Dec 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Fri 18 Dec 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Sat 19 Dec 2026, 8:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502
• Dr. Seuss' How the Grinch Stole Christmas
  Sun 20 Dec 2026, 2:00 PM — Theater
  Cumberland Theatre · 101 N Johnson St, Cumberland, MD 21502

Listings are seeded from venue and organiser calendars. See them on the map.