Jolly Trolley Holiday Tour and More Stuff to Do in Pittsburgh

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The Holiday’s are in FULL swing here in Pittsburgh! We have so many awesome events for you this season so lets kick it off by introducing this week’s Top 10 Things to Do in Pittsburgh!


Please keep in mind most events have been altered to fit CDC guidelines. We love bringing you the best events in Pittsburgh but the safety of the community is our priority. Please know all events require masks and follow strict social distancing proceeders. 

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Molly's Trolley

1. Jolly Trolley Holiday Tour

See Pittsburgh’s holiday traditions come to life from the comfort of a vintage-style trolley! Join Molly’s Trolleys Pittsburgh for a special sightseeing trolley tour this holiday season.

The Jolly Trolley is a 30-minute tour of Pittsburgh, perfect for all ages! Learn interesting facts about Pittsburgh holiday traditions, take photos, and sing along to holiday favorites. Beginning in the Strip District, this tour takes you throughout the city to discover the wonder and magic of the holidays in a unique and festive way. Jolly Trolley tours are going on NOW and run from 10 AM – 3:30 PM every 30 minutes on Saturdays and Sundays during the first three weekends in December.

Event Details
🗓 Dec. 12th + 13th | 10AM-3:30PM
Dec. 19th + 20th | 10AM-3:30PM
📍 Downtown Pittsburgh

Tis the season to be freezin’ and The PA Market has you covered! Stay home and enjoy one of their virtual wine, cocktail, or beer classes! Gather your friends or family and sign up for a class or two! They have classes that fit everyone’s interest!

Dates for Classes: 

  • Dec. 9th: Holiday Beer Experience 
    Dec. 16th: Wine Rules and When to Break Them
    Dec. 17th: Holiday Cocktail Making Class
    Dec. 30th: Sparking Wine from Around the World

The PA Market is also having a Holiday Market happening THIS WEEKEND! Join them in the courtyard for local small business vendors, winter cocktails, food and fun!

Event Details
🗓 Dec. 11th-13th 
📍 The PA Market

Live music, outdoor dining, and holiday light projections create a festive atmosphere for a new pop-up marketplace in parking lots and alleys along Penn Avenue, in partnership with Handmade Arcade. And, enjoy performances all weekend long on the EQT Sounds of the Season Stage.

When visiting the Merry Market, wear a face mask 😷 and practice social distancing.

Event Details
🗓 Dec. 12th + 13th | 12PM–7PM
📍 900 block of Penn Avenue

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Millie's Homemade Ice Cream

Shop local this season with Millie’s! Head to downtown Lawrenceville for local Pittsburgh vendors, steamy and creamy Millie’s hot chocolate, and so much fun! Please remember this holiday season to support local as much as you can.

🎄Dec 11: @maudespaperwinggallery metaphysical crystals & more! 💎
🎄Dec 12: @oh_candles @oliveandmarlowepgh 🕯 + 🫒
🎄Dec 19: @livefreshjuicery 🥥

Event Details
🗓 Dec. 11th + 12th + 19th| 5PM–10PM
📍 Lawrenceville 

Don’t miss your chance to take a socially distanced holiday photo with Santa on Saturdays at the History Center! Old Saint Nick will safely greet museum visitors this weekend from 11AM-2PM. Can’t make it this weekend?! Santa will be at the Heinz History Center Dec. 19th as well! Santa visits are included with regular admission.

Masks are required.

Event Details
🗓 Dec. 12th | 11AM–2PM
📍 Heinz History Center 


Nature Crawl | Dec. 11th

Pittsburgh Scarf Bomb | Dec. 12th

Holiday Laser Light Show | Dec. 11th 

Holiday Lights Mini Golf | Dec. 13th

Miracle Pop Up | Now-Dec. 31st

More Things to Do in CITY

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Liz McElhaney

Liz McElhaney

Liz is a City Manager for UNATION and author of the Stuff to Do in Pittsburgh City Guide. For more insight on the best events and things to do in the Pittsburgh area, download the UNATION app and follow @StufftoDoinPittsburgh on Instagram and Facebook.