Pittsburgh Events: Your Guide to December 29-January 4

As Pittsburgh closes the door on one year and cracks open the next, we’re encouraging you to get out for more than just New Year’s Eve. Stepping into the New Year on a good foot makes all the difference in how you start off 2026. The events from December 29 to January 4 deliver the cultural and artistic excellence that Pittsburgh is known for. Plus, you might as well have one last week of fun before inevitably having to get back to the “normal” routines on January 5.

Pittsburgh Events Happening December 29-January 4

Clue at the Benedum
Photo Courtesy of Benedum Center

Clue at the Benedum

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December 30-January 4, Benedum Center

PNC Broadway in Pittsburgh presents the hit stage adaptation of the beloved 1985 film and classic board game. Six guests, one manor, and endless possibilities keep audiences laughing—and guessing—through this fast-paced 90-minute whodunit. Will you solve the mystery before time is up?

First Night Pittsburgh 2025 by the Highmark Tree
Photo Courtesy of First Night Pittsburgh

First Night Pittsburgh 2025

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December 31, Downtown

One of the brightest nights of the year is First Night Pittsburgh. Downtown lights up with mobile bars and food trucks, ice rinks, family-friendly activities, and plenty of VIP passes to allow you to feel your fanciest to ring in the new year. Just wait until you see the wonder on your child’s face when the fireworks hit the sky. 

A person squeezes lemon onto a clam pizza.
Photo Courtesy of F&F Pizzeria

F&F Pizzeria NYE

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December 31, F&F Pizzeria

Why not spend your New Year’s Eve evening with renowned New York chefs Frank Falcinelli and Frank Castronovo (“The Franks”). F&F Pizzeria is offering its famous naturally fermented pizza and trattoria-style menu for the holiday. Celebrate with small plates, classic pasta dishes, and timeless cocktails like the Rust Belt Revival and The Olio Martini.

Square Cafe table shows off an arrangement of hot and cold drinks.
Photo Courtesy of Square Cafe

Square Cafe Cozy New Year’s Day Brunch & Lunch

January 1, Square Cafe 

After your late night out, let Square Cafe take care of you (and your possible hangover, too!) The bar and barista team will welcome 2026 with new specialty drinks. These include seasonal lattes like The Grinch and cocktails such as the Yule Mule and Mistletoe Mimosa, as well as a non-alcoholic Holiday Punch. 

A group of women sit and stand together in a gym space.
Photo Courtesy of Celebrations Bar, Banquet, and Grill

New Year New You Pilates & Mimosas

January 3, Celebrations Bar, Banquet, and Grill

Kick off the new year with positive vibes and a healthy start. This event welcomes all levels—no experience needed—for a refreshing Pilates session. After the workout, guests will enjoy a celebratory mimosa toast and a light breakfast where you can mingle with others and discuss your resolutions for the New Year.

Story by Kylie Thomas
Featured Photo Courtesy of The Pittsburgh Cultural Trust

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