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

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

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 […]
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 […]

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! […]

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 […]

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 […]

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.

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 […]

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!

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!!

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

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 - […]

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

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:

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

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!
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 […]

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 […]

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