Upcoming Halloween Events

BOOS & BREWS 5 featuring The Amish Outlaws & 10+ local bands across 2 days Halloween Extravaganza

 31 Thomas St, Cumberland, MD 21502-3909, United States 31 Oct 2025
HALLOWEEN

Annual Trunk or Treat

 15010 Baltimore Pike NE, Cumberland, MD 31 Oct 2025
TRUNK-OR-TREAT

Downtown Cumberland's Boo on the Bricks

 Baltimore, Centre, Liberty and Pershing Streets, Cumberland, MD, United States, Maryland 21502 25 Oct 2025
KIDS

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Upcoming Food & Drinks Events

Couples’ Night Pizza Making & Wine Pairing

 110-114 Baltimore St, Cumberland, MD, United States, Maryland 21502 23 Oct 2025
WORKSHOPS

Girls’ Night Out - Wine Pairing & Italian Appetizer

 110-114 Baltimore St, Cumberland, MD, United States, Maryland 21502 18 Nov 2025
WORKSHOPS

Bake Like a Pro: Mastering Advanced Techniques

 110-114 Baltimore St, Cumberland, MD, United States, Maryland 21502 4 Dec 2025
WORKSHOPS

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Upcoming Live Music Events

The Hoppers in Cumberland

 Allegany College of Maryland 2 Dec 2025
CONCERTS

Coltt Winter Lepley: Live @ Dig Deep 🪏

 2 Howard Street, Suite B, Cumberland, MD 17 Oct 2025
ART

Greg Larry + Maine Cousin's LOBSTER TRUCK!

 13006 Mason Road NE, Cumberland, MD, United States, Maryland 21502 17 Oct 2025
MUSIC

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Upcoming Trunk Or Treat Events

TRUNK-OR-TREAT @ BEDFORD RD FD

 13200 Bedford Rd NE, Cumberland, MD, United States, Maryland 21502 26 Oct 2025
TRUNK-OR-TREAT

Trunk or Treat

 11 Washington St, Cumberland, MD 12 Oct 2025
HALLOWEEN

Halloween Trunk Or Treat

1 Baltimore Street, Cumberland, MD 21502 28 Oct 2025
TRUNK-OR-TREAT

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Upcoming Festivals Events

Wizard Fest Cumberland

 Cumberland, MD. 7 Mar 2026
FESTIVALS

Solitary Man - Salute to Neil Diamond

 Ali Ghan Shrine Club 15 Nov 2025
ENTERTAINMENT

Be Well Arts Festival

 Blue Line Design and Landscape Center LLC 18 Oct 2025
HEALTH-WELLNESS FREE

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Trending Events in Cumberland

Trick or Treat with Liberty Tax!!

55 Henderson Ave, Cumberland, MD 21502 27 Oct 2025
TRICK-OR-TREAT

Celebration of Lights and Holiday Market at Canal Place

 13 Canal St , 21502 29 Nov 2025
HOLIDAY

FallFest

 Historic City Center, Cumberland, MD, United States, Maryland 21502 18 Oct 2025
ART

REVIVAL FIRE-307 Wallace St Cumberland, MD

 Fresh-Start Ministries 18 Oct 2025

Thrill the World Cumberland

 49 Baltimore St, Cumberland, MD 25 Oct 2025
ART

Flintstone Class of 1985 - 40th Class Reunion

 Oscars's Restaurant Cumberland 18 Oct 2025
WORKSHOPS

Harvest Gathering for the Whole Family!

 416 Pennsylvania Ave, Cumberland, MD, United States, Maryland 21502 31 Oct 2025
KIDS

Native plant class and seed harvesting

1 Commerce Dr, Cumberland, MD 11 Oct 2025
WORKSHOPS

Ink & Axes

 157 Baltimore St., 3rd Floor, Cumberland, MD, United States, Maryland 21502 11 Oct 2025
ART

Intermediate Buttercream – Borders & Blossoms

110-114 Baltimore St, Cumberland, MD, United States, Maryland 21502 14 Oct 2025
WORKSHOPS

Movie on the Lot

 301 Frederick St, Cumberland, MD 11 Oct 2025
ENTERTAINMENT

Lost History of Cumberland's Benjamin F. Stewart

 Allegany Museum 7 Nov 2025
NONPROFIT FREE

Advanced Buttercream – Writing & Floral Detailing

 110-114 Baltimore St, Cumberland, MD, United States, Maryland 21502 12 Nov 2025
WORKSHOPS

2025 Honors Day - RSVP for Bus and Banquet

 Park & Ride 11 Oct 2025
FREE

AYCE Breakfast Buffet Every Saturday & Sunday

13114 Warrior Drive, Cresaptown, MD 11 Oct 2025
KIDS

More things to do in Cumberland

Halloween
Food & Drinks
Live Music
Trunk Or Treat
Festivals
Christmas Wreath Workshops
Comedy
Thanksgiving
Christmas Markets & Fairs
Trick Or Treat
Music Festivals
Bar Crawls