Upcoming Events

Downtown Cumberland offers a robust variety of events year-round. Check back often for updates!


The Polar Express Train Ride
November 21 - December 23 • • Western Maryland Scenic Railroad-13 Canal Street

This Christmas season, step into the magic of The Polar Express - a beloved holiday tradition brought to life! Inspired by the classic film, this immersive train ride is the ultimate family experience. Sing along to the iconic soundtrack, sip hot chocolate and enjoy fresh-baked cookies as you journey to the North Pole - all […]

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Breakfast with Santa
Saturdays - November 29 and December 6 - 20 • Varies • Multiple Locations

Join Santa for a special holiday breakfast in downtown Cumberland! Call the restaurants for reservations and more information. November 29th - Cafe Mark 8:30 – 11:00 AM Reservations not accepted. Order from the menu. Kids under 10 eat free from the kids menu with an adult purchase. Parties limited to five guests. December 6 - […]

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Santa and Mrs. Claus Visits at The Rosenbaum
Saturdays - November 29 and December 6 - 20 • 1PM - 3PM • The Rosenbaum Building - 118 Baltimore Street in downtown Cumberland

Come share your Christmas wishes with Santa and Mrs. Claus in the lobby of The Rosenbaum building! Bring your phone or camera for photos.

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Christmas Tea Party at Gus & Oliver Children's Boutique
Saturday, December 6 • 11AM • 54 North Centre Street

Gus & Oliver will be hosting a Christmas themed tea party. We will be providing kid friendly tea snacks, hot cocoa, and warm apple cider. There will be Christmas ornament decorating, games and play. We are limiting this event to 12 children, if this fills up and there is enough interest, we will choose an […]

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Matt Mullins & the Bringdowns
Saturday, December 6 • 7-9pm • Gallery Stage-9 North Centre Street

Matt Mullins & the Bringdowns are a Y'allternative Rock Band. The stories in their songs are almost as diverse as the influences you hear in the music. Tickets are available here: Matt Mullins & The Bringdowns Tickets

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Megan Jean's Songwriter's Circle
Thursday, December 11 • 7-9pm • Gallery Stage-9 North Centre Street

Enjoy an unforgettable evening of music and storytelling as Megan Jean hosts an intimate Songwriter's Circle at Gallery Stage. This special night brings together a powerhouse lineup of regional talent-Jody Mosser, Gilbert Lee, Black Guy Fawkes, and Byrne Klay-for a collaborative performance celebrating the craft of songwriting. Each artist will share their original music, the […]

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Teddy Bear Tea & Holiday Art Workshop
Saturday, December 13 • 1PM - 3PM • The Women's Civic Club - 515 Washington Street Cumberland, MD

Adults $5 Children FREE Includes a Victorian Christmas Tour 301-722-6099 for more information

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Photos with Frosty
Saturday, December 13 • 3-5pm • Barkin' Basement-45 Baltimore St.

The Barkin' Basement will have Frosty at their store at 45 Baltimore Street on Saturday, December 13th from 3:00-5:00pm. Bring your camera or cell phone to get some holiday pictures!

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Winter Festival
Saturday, December 13 • 4PM-9PM • Downtown Cumberland on Baltimore Street

Winter Festival in downtown Cumberland includes a vendor market, live holiday music, kid's activities, firepits for roasting marshmallows, holiday characters, and more! FREE EVENT! Vendors include: AT&T, Autumn in August, Bending Glass Art, Bluecray Labs, LLC, Cheerful Confections, Chew On This-Jerky, LLC, Chris Carr Abstract Artist, Christina's Yarn Shop, The Crocheted Ginger, Flights of Scotland […]

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Mountainside Baroque - Festival of Lessons & Carols
Sunday, December 21 • 5PM • Emmanuel Episcopal Church - 16 Washington Street

For the thirteenth consecutive year, The Scholars of St. Cecilia, Mountainside Baroque’s resident chamber choir, will “ring in” the Christmas season with an ecumenical “Festival of Lessons and Carols,” featuring seasonal music, traditional carols, and readings by local clergy and officials. The event is free and open to the public, though a free-will offering will […]

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New Year's Eve Celebration - Chasing Midnight - A Piano Bar World Tour at The Arcadian Gallery
Wednesday, December 31 • 8PM - 11:45PM • The Arcadian Gallery - 47 Baltimore Street in downtown Cumberland

Get your tickets now for a blow out New Year's Eve celebration at the Arcadian, just a few steps away from the ball drop on Baltimore Street in Cumberland! On our first floor, enjoy around-the-world live music in a piano bar setting. Hop upstairs for an luxurious dinner buffet and cash bar. Just before midnight […]

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New Year's Eve in Downtown Cumberland
Wednesday, December 31 • 10PM - Midnight • Liberty Street Plaza - Baltimore and Liberty Streets

Join the celebration to welcome 2026! Music, giveaways, and the ball drop at midnight. All ages welcome! FREE EVENT!

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Groundhog Day Celebration
Monday, February 2, 2026 • 7AM • City Hall - 57 North Liberty Street in downtown Cumberland

Will it be an early spring or more winter? Join the annual Groundhog Day Celebration to find out! Winners of our Groundhog Day coloring contest will be announced and we will have hot beverages and cookies! Our own Queen City Charlie will make Cumberland's prediction!

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