Jeremy

Jeremy is the co-owner of Discover the Burgh. His favorite Pittsburgh activities include discovering unusual attractions, trying new breweries, and seeking out the city's best happy hours. He also runs the long-term travel blog, Living the Dream.

10 Reasons to Visit Pittsburgh in December 2026

While Pittsburgh in December marks the start of winter, the city itself is in holiday mode more than anything. We have just come off the heels of Light Up Night, and our Christmas markets, numerous Christmas events, and other festivities are at their peak.

Of course, as with all of our other monthly recommendations list, we also have a few great places to drink and museums to explore on the exceptionally cold days that are coming into the city because, let's face it, winter is coming and sometimes you just want to be inside.

So if you are looking for things to do in Pittsburgh in December, check out the following options.

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Pittsburgh Black Friday Deals to Check Out in 2025

Who doesn't love a great discount? Naturally, the Black Friday to Cyber Monday shopping weekend presents a wealth of shopping opportunities with discounted prices.

Naturally, Pittsburgh businesses and attractions are getting in on the Black Friday celebration as well.

So in this one, we thought we would share some of the best deals that we see popping up on our feeds to help you get the most out of exploring the city. From annual memberships and season passes to special releases at area breweries and distilleries, we've found some gems!

  • Notes: The following is a quick summary of some of our favorite deals we have found so far. Black Friday deals tend to come out on an on-going basis and we will be updating this article over time as we find more- so check back in the lead up to (and on) Black Friday for the most up-to-date set of deals. Additional terms and conditions may apply that are not included in our summary, please read deals in full prior to purchasing. Some discounts may be available now, while other promotions may only occur on Black Friday or Cyber Monday.
  • Although we're not offering a Black Friday special on our new book in 2025, we'd love it if you picked up a copy of The Pittsburgh Guidebook if you're doing any shopping as well!

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Phipps Conservatory’s Winter Flower Show – Holiday Magic

When it comes to holiday festivities, one of the best places in Pittsburgh to visit is Phipps Conservatory. Their winter flower show, which typically begins before Thanksgiving and runs until early January, is a celebration of the holiday season with festive art pieces, an array of gorgeous winter flowers, and some of the most beautifully decorated Christmas trees in Pittsburgh.

The 2025-2026 flower show is themed Holiday Magic and takes an elegant look at all things Christmas. With traditional decorations and subtle design elements, this one is simply beautiful.

As members of the conservatory, we got the chance to visit early in the season (running until January 4th, 2026) and wanted to share a few of our favorite rooms here!

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Bitter End Review – Speakeasy Vibes in Etna

We love a good speakeasy, and when we heard about Bitter End in Etna serving classic cocktails in a speakeasy ambiance (complete with green light above the front door), we made our way over as quickly as we could.

Although we had some concerns over the balance of our drinks, we always welcome more cocktail programs in the Pittsburgh region.

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How to Get the Most Out of Light Up Night in Pittsburgh

In Pittsburgh, the start of the holiday season is not ambiguous.

It is not after Halloween when department stores put out Christmas decorations (or do they do it before now?). It is not the day after Thanksgiving that many traditionally observe. It is also not the first snow sighting, December 1st, the fall time change, or any other arbitrary benchmark.

This one particular instance should not be up for debate, as the start of the Christmas season in Pittsburgh is Light Up Night- the Saturday before Thanksgiving.

In this guide, we want to share some of our favorite tips on how to get the most out of what is perhaps our favorite annual event in Pittsburgh!

Note: In 2025, Light Up Night will have some slightly modified event locations due to the on-going construction in Market Square. While this article is meant to be somewhat static year-to-year, we've noted some variations for 2025's festivities in this one.

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10 Reasons to Visit Pittsburgh in November 2026

November in Pittsburgh is truly a month of change. If we are lucky the start of the month still has mild temperatures and peak fall colors, and by the end of the month winter is starting to descend upon the region.

As such, while there may still be a number of outdoor activities to enjoy this month, depending on the weather forecast you may also want to start moving inside for some experiences!

So if you are looking for things to do in Pittsburgh in November, check out the following options.

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The Monks’ Bar Review – The Smallest Bar in PA Packs a Punch

In many cases, we often overlook that Pittsburgh hotels often have on-site cocktail bars. Some of these may be your conventional hotel bar, while others may be a bit more.

At The Priory Hotel in the North Side, you get what is perhaps the most interesting hotel bar experience in the city, for one unique reason- it is said to be the smallest bar in the state of Pennsylvania.

Yes, The Monks' Bar is tiny, and according to The Priory's website, it seats just 14 customers. So cozy up with your fellow patrons, get to know your bartender, and grab a drink from this limited, albeit expertly curated, bar menu!

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North Side Sandwich Week – The Best Sandwich Competition

Do you love sandwiches? We know the answer is yes, but we feel like we have to ask anyway.

Since you likely fall into this category, we're just going to cut to the chase and tell you that you need to make it over to the North Side to check out their annual sandwich week- taking place starting October 27th in 2025.

This annual event challenges all North Side restaurants to showcase a special sandwich for the week and throw down against each other for a judged event at The Priory Hotel to kick off the festivities.

We were invited to check out the opening night party in 2025 as guest judges and were able to get a sneak peek at some of the creations.

This is one party you don't want to miss in future years!

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Nine Two Five Review – Cocktails and More by Dancing Gnome

Ever since Dancing Gnome opened their massive new brewery in Sharpsburg, we always wondered what would happen to their original, more intimate location along Main Street.

In late 2025, Dancing Gnome announced that the original bar would be opened, renamed Nine Two Five (sometimes written Nine T(w)o Five- perhaps the most appropriate street-address-turned-bar-name you could ask for), and would be a welcoming, all-around bar with beer, cocktails, wine, food, and more.

Naturally, we visited this one on the first soft open, and while we would fully argue this one is a cocktail bar first that also has great local brews and PA wines, this one really has something for everyone- including a new food menu from Blue Sparrow!

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The Jack O’Lantern Extravaganza Brings 3,000+ Pumpkins to the Zoo

Every year, we always expect the Pittsburgh Zoo to put on some spectacular shows around the holidays.

In 2025, they get into the Halloween spirit by filling the zoo up with thousands of jack o'lanterns in the aptly named Jack O'Lantern Extravaganza.

So what all can you see in this one? We went to the zoo on a chilly fall evening to find out!

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