The Ultimate Guide to the Holidays in the South Hills of Pittsburgh

Finding Your Family Fun and More During the 2022 Holiday Season in the South Hills of Pittsburgh, PA

By Emily Papa, Macaroni Kid South Hills of Pittsburgh Publisher November 28, 2022

The lights are up, and the holidays are near! Have no fear, Macaroni KID is here! Here with your holiday family fun in the South Hills of Pittsburgh that is. This guide is packed with goodies to help parents living in the South Hills of Pittsburgh to not just survive the during holidays, but thrive. Well, surviving is great too. Whatever you're looking for mama, we got you. Looking for the best and brightest holiday lights that you can see? The best looking Santa in the 'Burgh? Discounts and inside scoops on local shopping? Daily event's PACKED with holiday festivities? Click on any of the photos below to take you to specific guides for more details on how to make the most out of your holidays in Pittsburgh, PA. 

***Please always check the links for more details and website for cancellations. Confirm with each establishment via their social media or calling them that nothing has changed since the creation of this guide as there are new COVID updates daily.***

 Bookmark this page and check back often as we are constantly adding more to the guide and individual pages. If there is something you'd like to see in here, submit the deets to this form or email with HOLIDAY GUIDE in the subject line. 

Last Updated: November 30th, 2022

Some of our Favorite Holiday Fun in the South Hills of Pittsburgh all season long:

Holiday Performances for kids and families in and around the South Hills of Pittsburgh, PA

A Lyrical Christmas Carol at Gargaro Theater

Scrooge sits in his house with not a kind word for anyone; he just wants to be left alone until the "humbug" of Christmas is over. But four ghostly visitors - his former business partner, followed by the Ghosts of Christmas Past, Christmas Present, and Christmas Yet to Come - show him the error of his ways, and by the time Christmas Day dawns, Scrooge is a changed person. The entire family will enjoy this timeless classic and Pittsburgh tradition, featuring your favorite holiday carols! Tickets are $25/each. Learn More HERE!

PBT's The Nutcracker

In this distinctly Pittsburgh production of a holiday classic, PBT’s The Nutcracker follows Marie, her Nutcracker prince and the Sugar Plum Fairy on a journey into the Land of Enchantment. Five fanciful scenes, more than 150 unique costumes and Tchaikovsky’s enduring score make The Nutcracker a can’t-miss holiday tradition. Performances from December 9th - December 28th with tickets ranging from $29-$125. Learn More HERE!

Winter Holiday Events for kids and families in and around the South Hills of Pittsburgh, PA

Jolly Trolley Holiday Sightseeing Tour every Friday, Saturday, and Sunday from November 25th to December 18th

See Pittsburgh’s holiday traditions come to life from the comfort of a vintage-style trolley! Special youth guests might even receive a small gift - sent all the way from the North Pole! Tickets are $15/adult and $10/children under 12. Learn More HERE!

Trolleys and Toy Trains at Pennsylvania Trolley Museum

Visitors will be able to ride on decorated trolleys, enjoy a guided tour, and view the Lionel Toy Train Layout. New this year is a festive I Spy challenge to go along with the train display. Cost is general admission. Trolleys and Toy Trains takes place on the first three Fridays in December; 2nd, 9th, & 16th. Learn More HERE!

Phipps Winter Flower Show and Light Garden: Holiday Magic

Holiday Magic Hours are daily from 9:30am-10pm November 18th - January 8th. Admission ranges from $11.95-$27.95 depending on visiting hours

Individual Holiday Happenings in the South Hills this Winter:

Cookies with Santa 

Enjoy cookies with Santa at Round Hill Park. Sunday, December 4th, noon - 2pm. Learn More HERE!

Beverly Brite Night

December 1st from 7-8:30 Beverly Road closes down for a night of holiday fun to include Santa, music, activities and fun for the whole family!

🎄 Grinchmas at Sarris Candies

🎄 Brookline’s Festival of Trees

🎅🏻 Santa Comes to HomevilleDecember 10, 2022

🎅🏻 2022 Santa ExperienceDecember 10, 2022

🎅🏻 Santa's Workshop at Opal Rose Boutique 🎁December 10, 2022

🎅🏻 Santa Photos at The Waterfront SENSORY FRIENDLY HOURDecember 11, 2022

🎅🏻 Santa's Workshop at The Red Fox WineryDecember 11, 2022

Come back for more updates or check the event calendar for a list of ALL events by day. Email if you'd like to see something added to this list.