‘Tis the Season: 2021 Holiday Events in Pittsburgh

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HO-HO-HOlyyy Moly! It’s that time of the year again! The time of goodwill and laughter while being surrounded by loved ones and enjoying those fun things that you can only experience during the holiday season.

Wondering how you’re going to fit everything in so you don’t miss out on the best events? Don’t get your tinsel in a tangle, we got you covered! Check out some of our favorite holiday events in Pittsburgh!

Please keep in mind most events have been altered to fit CDC guidelines and will be slightly different this year.

Holly Jolly Holiday Events in Pittsburgh

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📷 Miracle on Liberty

‘Tis the season for miracles and Miracle on Liberty is back this season! Come enjoy holiday-themed drinks, music and decorations. 

It’s Pittsburgh’s original holiday pop up bar so yinz know they go over-the-top. Although they won’t have individual igloos this year, they will be selling holiday glassware and donating a portion of the proceeds to charity.

Event Details
🗓 Nov 26–Dec.31st | 4:00pm–11:00pm
🎟 Free | No reservations
📍705 Liberty Ave

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📷 @socialitepittsburgh

The annual Holiday Market is back and still just as festive! In addition to shopping from small-businesses in festive chalets around Market Square, the Holiday Market will again feature live music on its centerpiece stage.

Event Details
🗓 Nov 19–Dec 23 (closed Thanksgiving)
🗓 Sunday | 11:00am–6:00pm
🗓 Monday–Thursday | 11:00am–8:00pm
🗓Friday & Saturday |  11:00am–9:30pm
🎟 Free
📍Market Square

Holiday Magic 2 'Tis The Season: 2021 Holiday Events In Pittsburgh 2022
📷 Phipps Conservatory and Botanical Gardens

The Winter Flower Show  will feature displays including a magical carousel floating on a pond, a cabin sitting a snowy forest of plants, a topiary animal display and a living room scene featuring furniture made of plants. This year’s theme is “Sparkle and Shine” and will include a brand new display of holiday trees, topiaries and more. Plus, 2021 marks the grand return of the Winter Light Garden, meaning the entire conservatory will be decorated and ready for your viewing pleasure!

Event Details
🗓 Nov 15–Jan 9 | 9:30am–11:00pm
🎟 $19.95 | Adult
🎟 $17.95 | Students & Seniors
🎟 11.95 | Child
📍Phipps Conservatory and Botanical Gardens

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📷 PPG Place

The UPMC Ice Rink at PPG Place is another one of the annual winter traditions that Yinzer’s adore. Come show off your skating skills with friends and family! Tickets must be purchased online and ahead of time to ensure socially distancing. Plus, make the most of your holiday trip Downtown and check out the People’s Gas Holiday Market located only a few minutes away!

Event Details
Holiday Hours 
Nov 19–Jan 9
🗓 Sunday–Thursday | 11:00am–10:00pm
🗓 Friday-Saturday | 11:00am–Midnight
🎟 Adults | $11.00$12.00
🎟 Children (12 & under) | $10.00–$11.00
🎟 Seniors (50 & up) | $10.00–$11.00
🎟 Discounts for Military members & first responders available with ID
🎟 Skate Rental | $5.00–$6.00
📍PPG Place

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📷 Pittsburgh Zoo & Aquarium

Zoo Light Drive Thru

Drive through the Zoo at night while guided by a themed audio tour as thousands of environmentally-friendly LED lights transform the park into an unforgettable winter wonderland! Enjoy over 80 animals, including 30 new additions and sing along to your favorite Christmas carols!

Event Details
🗓 Select nights starting Nov 26–Dec 30 | 5:15pm–9:45PM
🎟 $50.00
📍Pittsburgh Zoo & Aquarium

Ugly Sweater Bar Crawl 'Tis The Season: 2021 Holiday Events In Pittsburgh 2022

Ugly Sweater Bar Crawl

Really get into the holiday spirits at this year’s Ugly Sweater Bar Crawl. Enjoy holiday drinks, an ugly sweater costume contest, DJs, deals on food and more! Popular stops include The Flats on Carson, Carson City Saloon, Doughbar, Tiki Lounge, Local Bar and more. What are you waiting for?! Get your ticket, grab a beer and have a HOPpy Christmas!

Event Details
🗓 Dec 4 | 2:00pm–9:00pm
🎟 $14.99
📍East Carson Street 

Why You Should Shop Small

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It’s so important to support local, small businesses especially around the holiday season. These last few years have been tough on us all, especially those who are trying to sustain their business. We love supporting local and we want to encourage all of you to shop small this season!

More Holiday Events in Pittsburgh


Festival of Trees | Nov 19–20

Cirque Dreams Holidaze | Nov 26–27

Santa Trolley | Nov 26–28, Dec 4, 5, 11 & 12

Breakfast with Santa @ Hard Rock | Dec 4, 5, 11,12 & 18

Holiday Bazaar | Dec 4

Breakfast with Santa @ Vinoski Winery | Dec 5

Cookies & Cocoa with Mrs. Claus | Dec 11

Breakfast with Santa @ Coughlin’s Law | Dec 12

Christmas Tree Lighting | Dec 24

Holiday Lights

Dasher’s Drive-Thru Lightshow | Nov 1–Dec 31

Light Up Night 2021 | Nov 20

Sewickley Light Up Night | Dec 3

North Hills Hilltop Holiday Town | Dec 3

Santa’s Special Night: Joy of Christmas Light Show | Dec 8

Baldwin Holiday Festival | Dec 11

Boozy Parties + Crawls

Highland Village Holiday Party | Dec 2

Christmas Cookie Frost ‘n’ Sip @ Threadbare | Dec 9 & 16

Pittsburgh Santa Crawl 2021 | Dec 18

Rivers’ & Richards’ Ugly Sweater Christmas Party | Dec 21

Arts + Crafts

Christmas Porch Pot Workshop | Nov 26

Cosmic Christmas | Nov 26

Paint and Sip: Reindeer Porch Sign | Dec 1

Evergreen Swag Workshop  | Dec 3

Holiday Wreath Class | Dec 3

Christmas Wreath Workshop | Dec 4

Christmas Coasters | Dec 8

Holiday Floral Arrangement Class | Dec 9


Carnegie Christmas with Goats | Dec 18

Holiday Markets

Handmade Arcade Holiday Market | Dec 4

2021 Holiday Village Market | Dec 4

Winter Artists Market | Dec 11

Threadbare Winter Market | Dec 11

Crafts and Drafts Outdoor Holiday Market | Dec 12

Last Chance Holiday Market | Dec 17–19

Theater, Music & Movies

Pentatonix: The Evergreen Christmas Tour 2021 | Nov 29

A Charlie Brown Christmas: Live on Stage | Dec 3

A Motown Christmas | Dec 3

Pure Gold Christmas | Dec 4

FREE Polar Express Screening | Dec 4

Maddie Poppe’s Acoustic Christmas 2021 | Dec 5

Sounds of Christmas With The Latshaw Pops Orchestra | Dec 5

Street Corner Symphony Christmas | Dec 9 

Once Nothing Christmas Reunion Special | Dec 18

Trans-Siberian Orchestra-Christmas Eve & Other Stories | Dec 29

The Hip Hop Nutcracker | Dec 30 


NKBA Holiday Event: Tis the Season for Design | Nov 30

A Schitt’s Creek Christmas Trivia | Dec 2

Christmas Cookie Class | Dec 4

Oakmont Chamber of Commerce Christmas Home Tour | Dec 5

Oakmont Chamber of Commerce Holiday Gala | Dec 10

Vinoski Winery’s Annual Christmas Extravaganza | Dec 4 & 11

Saint Bartholomew Church Ugly Christmas Sweater 5k & 2 Mile Walk | Dec 11

The Mexican War Streets Winter Wonderland Extravaganza | Dec 18 


Make sure to follow along and see what cool and exciting things we will be bringing to the Burgh! 

For more holiday events, updates, grand openings, and MORE, follow us on Facebook or Instagram. Plus for more fun-filled events, download the UNATION app

Happy Holidays! 

Britta Moletz

Britta Moletz

Britta is a City Manager for UNATION and author of the Stuff to Do City Guide. For more insight on the best events and things to do near you, subscribe to our email, and follow us on social!