All The Best Ways to Celebrate the Holidays in Pittsburgh

In case you haven’t noticed, the holiday season is already underway here in Pittsburgh.

We can hardly believe it, either. You’d better get to decorating, and shopping too. But before you do, we wanted to make sure you didn’t miss the best seasonal celebrations this city has to offer.

So here you go. Happy Holidays, Pittsburgh!

Macy’s Holiday Windows

Macy's Window Pittsburgh
Macy’s Window Pittsburgh
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The store may be shuttered, but the holiday cheer lives on in the windows of the Macy’s/Kaufmann’s building downtown. Swing by Macy’s to experience the mini-miracle on Fifth Avenue.

S.W. Randall Toyes

SW Randall Toyes
image via swrandalltoys.com
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Since you’re already downtown, make a stop at Pittsburgh’s best and biggest toy store. S.W. Randall Toyes offers three floors of more toys than you could ever imagine. For 45 years they’ve been supply the city with “unique, wonderful, whimsical, rare, glamorous, awesome and exciting items.” So there’s no doubt you’ll find something for everyone on your shopping list.

The Miniature Railroad and Village

The Miniature Railroad and Village
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Don’t miss the world-renowned display that represents how people in our region lived, worked and played in our region from 1880-1930. The annual holiday display is a Pittsburgh tradition that got it start on Christmas Eve in 1920. In 1992 the Science Center took over and enlarged the display that includes replicas of Fallingwater, Forbes Field, a historic Pittsburgh incline and so much more.

Phipps Winter Flower Show and Light Garden

Phipps Winter Flower Show and Light Garden
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No matter the time of year, Phipps Conservatory is a pretty incredible place. But somehow it becomes even more magical during the holidays. The entire place, from the indoor exhibit rooms to the outdoor gardens, embodies the holiday spirit. Don’t miss the artful display of LEDs, decorated trees, colorful poinsettias, and the seasonally-themed Garden Railroad.

The Holiday Market

Market Square The Holiday Market
image via wesa.fm
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Tis the season for holiday shopping and festive activities in Market Square. The Square will be transformed into a one-of-a-kind shopping village featuring unique and culturally diverse vendors, food and performances. Horse-drawn carriage rides will take you on a tour around the city. And you can snag a photo with Santa who carved some time out of his schedule to hang out in Market Square.

The Nutcracker

The Nutcracker Pittsburgh
image via Pittsburgh Ballet
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The holidays take center stage at the Pittsburgh Ballet Theatre with their performance of the Nutcracker. It’s been called the best holiday show in the city, so you won’t want to miss your chance to experience this classic story, complete with more than 100 dancers, and Pittsburgh-inspired charm.

Kennywood Holiday Lights

Kennywood Holiday Lights Pittsburgh
image via kennywood
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It’s a special time of year at Pittsburgh’s favorite theme park. Kennywood’s Holiday Lights transform the park you know and love into a winter wonderland complete with one million lights, performances by local choirs, and a ride on the Gingerbread Express, plus a meet and greet with none other than Mr. Claus (Geez, this guy really gets around Pittsburgh).

Holiday Pops

Holiday Pops Pittsburgh
image via pgh symphony
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Have a holly jolly time with the Pittsburgh Symphony as they perform your favorite carols and much-loved holiday music. Be prepared for an extra dose of holiday cheer because Santa is stopping by for a carol sing-along!

Ice Skate at PPG Place

image via ppg place
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This year the rink at PPG Place is bigger and better than ever before. Believe it or not, It’s actually bigger than the rink at Rockefeller Square! The revamped rink can now accommodate some 350 skaters at once. Add 700 new skates to the mix, and Pittsburgh is all set to glide through the holidays.

Lawrenceville Joy of Cookies Tour

Lawrenceville Cookie Tour Pittsburgh
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Explore Lawrenceville while indulging on as many holiday cookies as you can stomach. Pop into 40 local businesses to do a little shopping and snag the shopkeepers favorite cookie, while crossing some items off of your holiday to-do list. Plus, there’s 14 additional “Take a Break Spots” suggested where you can enjoy a meal, coffee, or a cocktail!

A Musical Christmas Carol

Musical Christmas Carol Pittsburgh
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Join Scrooge, Tiny Tim, and the Pittsburgh CLO to celebrate the magical melodies of the holiday season. Let’s be honest, Christmas just wouldn’t feel right without this musical tradition. Grab your tickets today.

Shadrack’s Christmas Wonderland

Shadrack LIghts Pittsburgh
image via Shadrack’s
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A three-mile long holiday light show of epic proportions is coming to the Big Butler Fair Grounds. No, Butler isn’t Pittsburgh. But it’s only 25 miles away. Which is nothing when you consider that you’ll be making the trip to see the world’s largest drive-through, fully synchronized light show that uses millions of LED lights all set to the rhythm of the music.

Trans-Siberian Orchestra at Consol Energy

Trans Siberian Orchestra Pittsburgh
image via consol
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Experience the Ghost of Christmas Eve as performed by the Trans-Siberian Orchestra as their Winter Tour rolls into Pittsburgh. This Christmas-themed rock opera comes complete with extravagant lighting and pyrotechnic displays that promise to take the holiday excitement to new heights. 

First Night

image via pittsburghskyline.com
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Bring in 2016 at Pittsburgh’s art-focused New Year’s Eve party. First Night offers 150 events at nearly 50 indoor and outdoor locations within the 14-block Cultural District, culminating with the Countdown to Midnight and fireworks display. Dec 31.