ddc winterfest sat 20th
winterfest tree boy
Enjoy the last Saturday of this year’s WinterFest programming offering creative gift shopping, dining, and arts and entertainment.


Celebrating the holiday season in downtown Cumberland.

womens civic club
Victorian Christmas 2025

Presented By: Women’s Civic Club at the Magruder House • 515 Washington Street, Cumberland
Date/Time: December 20, 2025 • 5:00 PM to 8:00 PM
Price: $5.00 for adults, kids under 12 free
(518) 527-8129sherylbrown.wcc@gmail.com
Walk through a historic Victorian home and see the tasteful Christmas Decorations and period furniture. A must see. We are on Historic Washington St. It is not to be missed.

mezzos image
Breakfast with Santa at Mezzos

114 S. Centre Street • 301-777-7750

Four Seatings:

10:00 AM, 10:45 AM, 11:30 AM, 12:15 PM
Adults/$12; Children 12 and under/$7

Reservations Required.

Scrambled Eggs • Sausage • French Toast • Chicken Tenders • Fries • Apple Juice • Milk

winterfest santa
Visit with Santa at the Rosenbaum

118 Baltimore Street • 1 – 3 PM

Santa and Mrs. Claus will at The Rosenbaum to meet and greet with the kids.
Bring your camera or cell phone for photos. FREE!

lily book signing
Lily Books & Cafe

Saturday, December 20 • 12 – 2 PM

This Saturday, December 20th, we will have Jon Ketzner in the store for a book signing from 12pm to 2pm!
We will have copies of his books for sale, or bring in your personal copy. We hope to see you there! lily books & cafe c final

cumberland theatre sherlock
A Sherlock Carol

Cumberland Theatre
101 N. Johnson Street • 301-759-4990info@cumberlandtheatre.com

A Sherlock Carol – Step into a world where mystery meets holiday magic! A Sherlock Carol arrives at Cumberland Theatre December 4th–21st, blending Dickens’ heart with Doyle’s wit in one unforgettable seasonal adventure.

Join us for a festive whodunit perfect for longtime fans and first-time visitors alike.
Return to Baker Street. Rediscover Christmas. Solve the season.

Get your tickets now at cumberlandtheatre.com offering pricing options for adults, students, and seniors.

art for giving 02
Art For Giving

C. William Gilchrist Museum of the Arts 1 – 4 PM
104 Washington Street • www.gilchristgallery.com • 301-724-5800

Something very special is happening on Washington Street.

What’s the big deal? All artwork is locally made and varies in style. Proceeds from sales benefit local art and the Gallery. 

Artwork can be purchased and taken home the same day, making it perfect for holiday gifting. Take a virtual walk through the artwork below. Find one that speaks to you or a loved one?

rug shop flyer
A Very Hippy Holiday Takeover at the Rug Shop

December 20 • 1 – 9 PM
37 N Centre Street • 301-723-0818

Come join The Rug Shop and DJ J.Gray as we host a “Very Hippy Holiday Takeover”!
DJ J.Gray will be set up on Tilly’s Living Room Stage to spin, and with his Appalachian Organics Tie Dyes.

The Rug Shop is BYO for all consumables, so please visit our neighbors on North Centre Street for all of your consumption needs.
NO RULES AT THE RUG SHOP

winterfest polar express
The Polar Express™
Western Maryland Scenic Railroad


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 in your favorite pajamas!

Click to view dates and pricing

Enjoy Western Maryland Scenic Railroad Polar Express Trains. Reservations required at wmsr.com

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