As part of their Winter Music Series, the Pittsburgh Playhouse at Point Park University is excited to host Christmas Live with Joe Serafini! The musician and actor is best known for his role as Seb in High School Musical: The Musical: The Series, but locals know him as a longtime performer with Pittsburgh’s CLO Academy.

Swing into the season with the Pittsburgh Jazz Orchestra Holiday Show! On Friday, December 19 at 7:00 PM, the world-class jazz musicians bring the magic of the holidays to the Pittsburgh Playhouse at Point Park University.

For three weekends only, located in the Encore Building at 100 7^th St., The Merry Marketplace will return with international vendors, including the highly anticipated pop-up, the Black Market!

The Industrialist Hotel, located at 405 Wood St. downtown, has converted its lounge, The Rebel Room, into a vintage holiday wonderland pop-up bar!  Located on the second floor of the hotel, The Atomic Tinsel Cocktail Club had its opening night on Friday, November 21, 2025.

This year, Pittsburgh will celebrate its 64th Annual Light Up Night on Saturday, November 22, 2025, at various locations throughout the downtown area. Sponsored by Highmark, Light Up Night has become a Pittsburgh tradition, expanding into the surrounding neighborhoods and suburbs, but the one downtown boasts the most attendees by far. With several different activities, including vendors, tree lighting, fireworks, and various small parties throughout the city, Light Up Night is back and bigger than ever!

Looking to get ahead on your holiday planning? Valozzi’s is bringing the festive cheer early with their exciting “Christmas in July” catering promotion!