Upcoming Events

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


Cumberland Juggling Club
Tuesdays • 5-6PM • Constitution Park

Cumberland Juggling Club is a free club that welcomes all skill levels! Join us at our weekly meetings to hang out, learn, and practice. Club time can be used to learn new skills, practice routines, get feedback, or just hang out with other members. No sign-up or pre-registration required. Equipment for the following is provided, […]

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Draw & Sip Workshop
Wednesday, November 5 • 7:30pm • Arcadian Gallery - 47 Baltimore St

Improve your perspective drawing with Arcadian Gallery Director, Christoper Sloan, on Wednesday, November 5 starting at 7:30 pm.

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GoldenOak at Gallery Stage
Friday, November 7 • 7-9pm • Gallery Stage-9 North Centre Street

GoldenOak blends folk traditions, sibling harmonies, and modern consciousness. From their breakout debut Pleasant St. to the award-winning Foxgloves EP and their latest album Room to Grow, their music carries both urgency and hope. Tickets are available here: https://www.tickettailor.com/events/gallerystage/1866189

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Denim & Diamonds Fundraiser for The Cumberland Theatre
Saturday, November 8 • 7PM - 9PM • 634 Washington Street, Cumberland

Join us for a fun night of food, drink and fun celebrating the Cumberland Theatre. Hosted in the lovely home of Rommel Gonzaga and Joel Hoover, its the perfect chance to come together and kick off the festive season! The Cumberland Theatre is in need of your support to continue to create professional quality entertainment […]

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Megan Jean's Secret Family
Saturday, November 8 • 7-9pm • Gallery Stage-9 North Centre Street

After a fiery first night feat. Dre Anders, Megan Jean's Secret Family is back for the second chapter of their three-show residency at Gallery Stage - and they're just getting warmed up. This genre-defying quartet brings a fearless blend of rock, soul, country, and jam - think '70s swagger meets '90s edge, wrapped in powerhouse […]

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Juliet Lloyd Trio
Friday, November 14 • 7-9pm • Gallery Stage-9 North Centre Street

Experience the soulful magic of Juliet Lloyd live! With a voice likened to Patty Griffin and Carole King, Juliet blends folk, pop, soul, and rock in captivating performances. Her 2024 album Carnival has been hailed for evocative storytelling and raw honesty. Don't miss this award-winning singer/songwriter whose dynamic sound has enchanted audiences across the country! […]

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Holiday Wine Tasting - East of Bordeaux at The Arcadian Gallery
Thursday, November 20 • 7:30PM • The Arcadian Gallery - 47 Baltimore Street in downtown Cumberland

Please join us for our special Holiday Wine Tasting event, East of Bordeaux. We'll introduce you to some of our favorite wines from newly popular wine-producing regions including Slovenia and Croatia, along with delicious pairings. While we're sipping, Hungarian keyboard artist Peter Czifra will entertain us with a rich tapestry of regional music. Tickets are […]

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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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Opening Reception for Vanishing Point
Friday, November 21 • 6-8pm • Arcadian Gallery - 47 Baltimore St

The Arcadian Gallery will host the opening reception for its new exhibit, Vanishing Point, on Friday, November 21st from 6-8pm. Vanishing Point: A life spent observing, conserving and painting birds. The Art of Logan Hartlaub.

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Not Reely Dan
Saturday, November 22 • 8-10:15pm • Loft 129-129 Baltimore Street

Not Reely Dan is back!! Not Reely Dan, the east coast's premiere Steely Dan Tribute Band, returns to American Woodmark Stage at Loft129 for the second of two special 2025 appearances. The group includes the region’s finest musicians and features exclusively the music of the classic Rock and Roll Hall of Fame band. Band members […]

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Cumberland Christmas Tree Lighting
Friday, November 28th • 5PM-8PM • Downtown Cumberland on Baltimore Street

Join the celebration downtown on Baltimore Street for the annual lighting of our Christmas tree! Holiday music, festive lights and the arrival of Santa and Mrs. Claus!

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2nd Annual Canal Place Celebration of Lights & Holiday Market
Saturday, November 29 • 2-8pm • Canal Place-13 Canal Street

Celebrate Shop Small Saturday and check out the 2nd Annual Canal Place Celebration of Lights & Holiday Market on Saturday, November 29th from 2 to 8 pm! Enjoy live entertainment, food, drinks, cocoa and cookies, photos with Santa for kids and pets, craft & specialty shopping, Toys for Happiness, tree lighting, and more!!

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2nd Annual Holiday Wine Tasting & Shoppe to Benefit The Cumberland Theatre
Saturday, November 29 • Noon - 4PM • Ottaviani's Tasting Room - 27 North Centre Street, Cumberland

FOOD! WINE! FUN! All proceeds benefit The Cumberland Theatre. $30 per person and includes tasting of nine wines and souvenir glass. Get tickets at the door or online at cumberlandtheatre.com

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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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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:

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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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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!

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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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