Winter holiday events in Cumberland, MD
2025 Breakfast with Santa in Middleburg
Saturday at 7:30 AM
Middleburg · Middleburg Community Charter School, North Madison Street, Middleburg, VA, USA
2025 Breakfast with Santa in Middleburg
Saturday at 7:30 AM
Middleburg · Middleburg Community Charter School, North Madison Street, Middleburg, VA, USA
Amplify MedTech First Anniversary Celebration and Holiday Party
Tuesday at 5:00 PM
Frederick · I-270 Innovation Labs
Amplify MedTech First Anniversary Celebration and Holiday Party
Tuesday at 5:00 PM
Frederick · I-270 Innovation Labs
Pittsburgh Holiday Festival
Sat, Dec 13, 11:00 AM
Monroeville · Monroeville Convention and Events Center
Pittsburgh Holiday Festival
Sat, Dec 13, 11:00 AM
Monroeville · Monroeville Convention and Events Center

Have yourself a Jazzy Little Christmas at St. Peter's Episcopal Church
Sat, Dec 6, 7:00 PM
Poolesville · 20100 Fisher Ave

Have yourself a Jazzy Little Christmas at St. Peter's Episcopal Church
Sat, Dec 6, 7:00 PM
Poolesville · 20100 Fisher Ave
Spires at Christmas
Sat, Dec 20, 7:30 PM
Frederick · Visual & Performing Arts Center - Frederick Community College
Spires at Christmas
Sat, Dec 20, 7:30 PM
Frederick · Visual & Performing Arts Center - Frederick Community College
A Place To Be’s 15th Annual Holiday Show - A Small Town Celebration
Sun, Dec 21, 3:00 PM
Middleburg · Salamander Middleburg
A Place To Be’s 15th Annual Holiday Show - A Small Town Celebration
Sun, Dec 21, 3:00 PM
Middleburg · Salamander Middleburg
Dueling Piano at Springfield Manor
Fri, Dec 12, 7:00 PM
Thurmont · Springfield Manor Winery & Distillery
Dueling Piano at Springfield Manor
Fri, Dec 12, 7:00 PM
Thurmont · Springfield Manor Winery & Distillery
Jason Kendall Productions Presents "Holiday Road" 13th Annual Holiday Show
Sun, Dec 7, 5:30 PM
Pittsburgh · Wyndham Grand Pittsburgh Downtown
Jason Kendall Productions Presents "Holiday Road" 13th Annual Holiday Show
Sun, Dec 7, 5:30 PM
Pittsburgh · Wyndham Grand Pittsburgh Downtown
