Saturdays between Thanksgiving and New Years Eve, Downtown is celebrating the season.
Friday, November 28 • 5 PM
A true “magic movie moment” when our beautiful City Center streets fill with families and children to see the City Tree. Santa arrives dramatically and when the switch is thrown, Cumberland lights up all the way to historic Emmanuel Church on the hill. Open houses abound and the spirit of the holiday season soars.
Saturday, November 29
The perfect time to explore City Centre’s growing community of lively shops, specialty goods. Program include Breakfast With Santa, Santa visits indoors at The Rosenbaum from 1 – 3 PM and a Celebration of Lights and Holiday Market at Canal Place. Enjoy Western Maryland Scenic Railroad Polar Express Trains. Reservations required at wmsr.com.
Saturday, December 6
Breakfast with Santa at the Culinaire Café Gateway Center. Two Seatings: 9 AM and 10:30 AM
Visits with Santa at the Rosenbaum: 1 – 3 PM
Matt Mullins & the Bringdowns: 7 – 9 pm – 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. Click here for tickets.
Enjoy Western Maryland Scenic Railroad Polar Express Trains. Reservations required at wmsr.com
Saturday, December 13 • 4 – 9 PM
Children’s Activities • Visit with Santa • Artisan Craft Vendors
Carriage Rides • Music • Fire Pits • S’mores • Sponsors
Streets closed to vehicle traffic, open containers permit.
Saturday, December 20
Breakfast with Santa at Mezzos
Visits with Santa at the Rosenbaum: 1 – 3 PM
Enjoy Western Maryland Scenic Railroad Polar Express Trains. Reservations required at wmsr.com
Wednesday, December 31 • 10:00 – Midnight
Ring in the New Year with Cumberland’s annual New Year’s Eve Celebration and Ball Drop, complete with fireworks at midnight! Make an early New Year’s resolution to celebrate the start of 2026 in beautiful downtown Cumberland. Music by DJ Jimmy Hook, free NYE party favors, and more!
Open Container Permitted • Baltimore Street Closed to Vehicle Traffic
The Polar Express Golden Ticket – Distributed to WMSR Polar Express Riders with discounts available at participating downtown merchants.
Lodging Options – https://www.mdmountainside.com/places-to-stay/
Scenic Railroad Tickets – www.wmsr.com