When winter rolls in, getting involved in local events becomes its own kind of survival skill. Instead of settling into the couch-cocoon routine, stepping out into the city gives you a shot of energy and a reason to stay connected. Pittsburgh’s winter gatherings spark creativity, lift moods, support small businesses, and make the season feel a little brighter. They turn cold months into moments of community, curiosity, and warmth. Showing up isn’t just fun. It keeps your world feeling bigger, lighter, and a lot more alive.

December

Around the City:

The Peoples Gas Holiday Market
November 21 - December 24 | 7th St and Penn Ave, Downtown
The Peoples Gas Holiday Market turns Downtown Pittsburgh into a charming winter village, filled with cozy chalets, handcrafted gifts, and festive cheer. It’s a seasonal staple that invites visitors to wander, shop, and soak in the warmth of the holidays right in the heart of Market Square.

Handmade Holiday Market
December 5 & 6 | David L. Lawrence Convention Center
Pittsburgh’s biggest handmade shopping experience returns to the David L. Lawrence Convention Center on December 5–6. Now celebrating 21 years in 2025, the Handmade Arcade Holiday Market brings together more than 275 makers offering one-of-a-kind, handcrafted goods you won’t find anywhere else.

Oz Dust Ball
December 6 | Soldiers and Sailors Memorial
Step into the shimmering swirl of the Oz Dust Ball, landing in Pittsburgh on December 6th, 2025. Inspired by the lush, larger-than-life universe of Wicked, this formal fever dream fills the night with soaring performances, electric dance numbers, spirited sing-alongs, enchanted treats, bespoke cocktails, and interactive moments that blur the line between guest and cast in the best possible way.

Candlelight: Christmas Carols on Strings
December 27 | Omni William Penn Hotel
Candlelight concerts transform familiar spaces into glowing, immersive musical escapes, offering Pittsburgh a fresh way to experience live performance. Set beneath a warm sea of candlelight, this special Christmas Carols on Strings performance at the Omni William Penn Hotel invites guests to slow down, listen deeply, and soak in the season’s soundtrack like never before.

Phipps Holiday Magic
All month | Phipps Botanical Garden
Phipps’ Holiday Magic transforms the conservatory into a glowing wonderland of lights, vibrant displays, and seasonal whimsy. It’s a Pittsburgh winter tradition that invites guests to wander through warmth, color, and holiday cheer at every turn.

At Bakery Square:

Yoga in the Portal
Every Saturday | The Portal
Join us for a serene escape at The Portal in Bakery Square every Saturday. Find your inner peace and rejuvenate with our weekly yoga session. Namaste!

Page Turners Book Club
December 7 | Conservatory
Discover, discuss, and connect with fellow book lovers at the Page Turners Book Club hosted by @pghgoodreads! Munch on delicious food while chatting about your favorite reads. Enjoy awesome vendors and fun activities each month!

Holly Jolly Holiday Party
December 13 | Bakery Square
We're bringing all the festive fun to town! Experience a winter wonderland right in the heart of Bakery Square! Join us for an incredible holiday event that you won't want to miss! This event is family-friendly, FREE, and open to the public.

Live Music by Radiant Strings
December 14, 21, 28 | The Portal
Radiant Strings is a Pittsburgh-based string ensemble comprised of classically trained musicians and is the ideal blend of classical refinement, modern edge, and infectious energy. This is their fourth holiday season spent performing at BKSQ and they are so excited to be continuing the tradition!

Shady Side Academy Orchestra Performance
December 15 | The Conservatory
Come catch the Shady Side Academy Orchestra in action as they serve up a merry mix of classical hits and holiday tunes.

Noon Year's Eve
December 31 | Conservatory
Why wait until midnight?! Party with the kiddos as we watch the ball drop and welcome in 2026 with Bakery Square's Noon Year's Eve party!

Find more December events at BKSQ here.