Saturdays between Thanksgiving and New Years Eve, Downtown is celebrating the season.
Friday, November 27
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.
Check back for more information.
Saturday, November 28
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.
Check back for more information.
Saturday, November 28 • 13 Canal Street
Event by Passages of the Western Potomac Heritage Area & Canal Place
Join us to kick off the official holiday season at Canal Place on Small Business Saturday, Nov 28th. This event is free to the public. Shop our stores and vendors for the perfect Christmas gifts, grab dinner or a snack at one of the restaurants or food trucks. Enjoy live entertainment, photos with Santa for your kids and pets and lighting up Canal Place. We are kicking off the holidays in style and look forward to celebrating with you!
Sponsorships open for the 2026 Celebration of Lights:
Bring the kids and join Santa for breakfast and holiday fun.
Dates and locations coming soon! Check back.
Saturday, December 5
Check back for more information.
Enjoy Western Maryland Scenic Railroad Polar Express Trains. Reservations required at wmsr.com
Saturday, December 12 • 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 19
Check back for more information.
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
Check back for more information.
69 Baltimore Street • www.thewillshotel.com • 240-245-2331
Stay right in the heart of things on the downtown Cumberland Mall!
The Wills Hotel is a 20-room boutique stay designed for those who want to be close to the action without sacrificing comfort. Whether you’re here for a festival, the GAP Trail, or a night out, everything starts—and ends—right here.
We have an onsite restaurant & bar, 1867 A Modern Chophouse.
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