Photo courtesy of Pittsburgh Downtown Partnership.

The city starts getting festive on Friday, Nov. 19, with some new twists to the annual holiday celebration. The biggest change is moving Highmark Light Up Night from its traditional Friday spot to Saturday, providing an opportunity to introduce bonus programming the night before.

Pittsburgh Downtown Partnership wants workers to stick around after clocking out on Nov. 19 to experience a wide selection of activities, including the Merry Karaoke Team Tournament. Teams of amateur singers will compete for a $5,000 cash prize, which will be split between winners and a nonprofit organization of their choosing. Registration is still open.

Peoples Gas Holiday Market. Photo courtesy of the Pittsburgh Downtown Partnership.

Early-bird shoppers can also peruse the Peoples Gas Holiday Market, get a first glimpse of the World’s Largest Pickle Ornament (which had quite an adventure last year), grab an adult beverage at EQT Plaza and enjoy live music.

The UPMC Rink at PPG Place will showcase figure skating and a lighting ceremony for the new tree at center ice. The public is invited to skate before and after the programmed events.

Highmark Light Up Night, which marks its 60th anniversary, will be held the following day, Nov. 20, with traditional and contemporary holiday attractions. And they are free!

American Authors. Photo courtesy of the Pittsburgh Downtown Partnership.

The multi-platinum, New York-based band American Authors will take the BNY Mellon Stage at the Allegheny Overlook on Fort Duquesne Boulevard with local acts Donora and Lyndsey Smith & Steeltown Horns.

Appearing on the Highmark Main Stage at Penn Avenue and Stanwix Street will be the Mr. Smalls All-Star Beatles Tribute group, which features more than 15 local musicians performing Beatles classics. Pittsburgh icon Joe Grushecky and the Houserockers, and Blues songstress Miss Freddye will also appear.

The EQT Jazzmasters Stage will offer The Daniel May Trio with Dwayne Dolphin and George Heid III. The performance will include special guest vocalists Anita Levels, Maria Becoates-Bey and more playing jazz holiday favorites and the music of Fred Rogers. The Merry Karaoke Team Tournament winners will sing seasonal tunes aboard a giant, motorized BJ’s Wholesale Club shopping cart.

Photo courtesy of the Pittsburgh Downtown Partnership.

Other attractions and entertainment options include the 19th Annual Gingerbread House Display & Competition, an ice carving demonstration, Zoom interactions with Santa Claus, a Zambelli rooftop fireworks display at the City-County Building at 5 p.m., the Highmark Christmas Tree Lighting at 6 p.m. and another round of fireworks at 9:30 p.m.

For more November celebrations, check out our list of 13 November events not to miss in Pittsburgh.

Kristy Locklin

Kristy Locklin is a North Hills-based writer. When she's not busy reporting, she enjoys watching horror movies and exploring Pittsburgh's craft beer scene.