WinterFest Market 2026

ddc winterfest wintermart event 26


Why not make it a holiday weekend in Cumberland Historic City Center?

Do a little holiday shopping in our delightful and locally owned shops. Enjoy a meal, dessert, or a beverage or two in one of our locally owned eateries or pubs. Absorb a little history at The Allegany Museum and Gordon Roberts House. Put your PJs on and enjoy a ride on the Polar Express. Enjoy the holiday small town charm of Cumberland, Maryland.

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WinterFest Market at Historic City Center

Saturday, December 12 • 4 – 9 PM

Children’s Activities • Visit with Santa • Artisan Craft Vendors
Music • Black Magic Circus Entertainment – Sugarplum Fairies
Carriage Rides • Fire Pits • Toasted Marshmallows

Streets closed to vehicle traffic, open containers permit.

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Breakfast with Santa

Culinaire Café
110-114 Baltimore Street • 301-784-5413
Saturday, December 12

Details coming! Please check back.

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Breakfast with Santa

Queen City Creamery
152 Baltimore Street • 240-727-7779
Saturday, December 12

Details coming! Please check back.

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Visit with Santa at the Rosenbaum

118 Baltimore Street • therosenbaumbuilding.com
Saturday, December 12 • 1:00 – 3:00 PM

guitar necks
Main Stage • Liberty Street

Details coming! Please check back.


ej logoSponsored by your local Edward Jones Teams.

winterfest black magic
Black Magic Circus LED

Saturday, December 12 • 4 – 9 PM
Hypnotic LED Flow Artistry.

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Photos with Frosty at Barkin’ Basement

Saturday, December 12 • 3 – 5 PM • 45 Baltimore Street • 301-777-0826

Bring your furbabies or your kids or both, and take a photo memory with Frosty. He’ll be waiting for you in front of Barkin’ Basement. There will be treats for your two-legged and four-legged family members. And while you’re at it, do a little holiday shopping at Barkin’ Basement.

winterfest carriage rides
FREE Carriage Rides

Saturday, December 12 • 5 – 7 PM
Located by the Cumberland Police Station

Enjoy a ride around town in a carriage.

Taylor Carriage Rides will be located by the Cumberland Police Station. Hop on in and enjoy the ride. 

winterfest market polar xpress
The Polar Express Train Ride

Western Maryland Scenic Railroad
13 Canal Street • (301) 759-4400 • wmsr.com

Experience the magic of The Polar Express™ Train Ride, where the beloved holiday story comes to life with music, treats, and a festive journey to the North Pole!

Reservations Required. https://wmsr.com/the-polar-express-train-ride

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The Wills Hotel

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.

winterfest weekend
MAKE IT A WEEKEND!


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