It’s the most wonderful time of the year! The holiday season is (almost) upon us and Pittsburgh is celebrating – a lot!
Below we have rounded up over 50 (!) holiday events that have already been announced in Pittsburgh! Be sure to bookmark this page and check back later in the season. We will keep adding events as we find them!
Did we forget your favorite holiday event? Leave it in the comments below!
The Ultimate Pittsburgh Holiday Festival Guide:
Wholey’s Oyster Festival
November 9-11
Wholey’s in the Strip District is celebration oyster season with an Oyster Festival, featuring oysters, special sales, live entertainment, shucking demonstrations, and lots of oyster varieties, like Chesapeake Bay, Fat Baby, Connecticut Blue Points, James River and more. See more on their Facebook page.
The Grinch 3D Screening
Starts November 9
Screenings of the The Grinch at The Rangos Giant Cinema begin on November 9 and will run through the holiday season. More information can be found online.
German Christmas Market in Harmony, PA
November 10-11
Stop by Historic Harmony village for two days of German music and entertainment, food, artisan vendors, and holiday shopping! Admission is $7 for adults, $5 for seniors, $3 for students, free for children younger than six. Event is a fundraiser for Harmony Village, which is located off I-79, just north of Cranberry Township.
Pre-Christmas Sale at Soergel’s
November 11
For this is a one-day-only event, everything in Home Accents and the Garden Center will be at least 20% OFF.
Light Up Night
November 16
It’s the start of the holiday season in Pittsburgh! There will be 5 stages of music, fireworks, food, and more. Santa flips on the lights at 5:45 p.m.
Monongahela Holiday Arts and Crafts Show
November 16
As part of Monongahela’s Light Up Night, The Monongahela Fire Department is hosting a Holiday Arts and Craft Show with vendors, a Chinese auction, baked goods, and more.
Greater Pittsburgh Arts & Crafts Holiday Spectacular
November 16
One of the area’s biggest and best Christmas craft festivals  is located at the Monroeville Convention Center and features over 290 indoor booths of arts & crafts in two huge exhibit halls. There will be pre-packaged foods including gourmet dips & drink mixes, jellies & jams, home baked goods, kettle korn, cinnamon roasted almonds & nuts, candies, fudge and more.
Drive Thru Christmas Wonderland Light Show
November 16-Decmber 6
The three-mile route is a filled with hundreds of thousands of brilliant LED lights perfectly dancing to music.
Friendsgiving at Greenhouse Winery
November 17
Celebrate Thanksgiving with your friends at Greenhouse Winery. Guests will enjoy wine, catered meal, and live music. Tickets can be purchased online.
North Belle Vernon Light Up Night 2018
November 17
North Belle Vernon Light Up Night will feature holiday music, a bonfire, and holiday refreshments.
Oakmont’s Hometown Christmas Parade & Event
November 17
Enjoy a Christmas Tree Lighting Ceremony, Free Oakmont Bakery Cookies, Pictures with Santa Santa, Food Vendors, Chinese Auction, 50/50 Drawing, and more at the Oakmont Hometown Parade.
Holiday Open House Public at The Artsmiths of Pittsburgh
November 17
As the official kickoff to the holiday season, Artsmiths is offering Coffee, Cocoa, Cider and Cookies along with goodie bags from our artist elves for those who spend more than $50! Shop homemade goods and enjoy treats.
Mars Fall Craft Show
November 17
Held in the Mars High School and Middle School, this event features over 250 crafters with all handmade product.
Let It Glow Celebration at The Waterfront
November 18
This free event features Santa’s arrival by firetruck, live music, Pop-Craft activity, Kids activities, Holiday characters, Strolling carolers, and a Tree Lighting at 6pm.
Pittsburgh VegFEAST 2018- Plant Based Thanksgiving
November 18
Pittsburgh’s annual plant based Thanksgiving dinner 2018. Roomy venue and 2 serving lines! Feast on Pittsburgh’s best vegan food including dinner menu by: Onion Maiden, Fortuitea Cafe, Reed&co, The Happy Vegan, and more TBA.
Holiday Tours of Clayton
November 21 – January 6
Holiday tours of Frick’s Point Breeze mansion begin on November 21st. The home will be lavishly decorated to re-imagine the events of 1908, when Helen Clay Frick made her debut into society.
WPXI Holiday Parade
November 24
The annual WPXI Holiday Parade Presented by Neighborhood Ford Store in the heart of downtown Pittsburgh. Watch as local celebrities, talented singers & dancers, marching bands, festive floats, billowing balloons parade Downtown. Pittsburgh native and American Idol finalist, Gabby Barrett is scheduled to perform, as well as appearances by the World Famous Harlem Globetrotters, extreme pogo jumpers from Xpogo & more!
Small Business Saturday
November 24
Support small businesses in Pittsburgh! Shop for your holiday presents at Pittsburgh’s plethora of locally-owned businesses. Many stores will have discounts and treats.
Charlie Brown Christmas Live on Stage
November 25
Join Charlie Brown and the whole Peanuts gang as everyone’s favorite holiday classic comes to life on stage at the Byham Theater. More information online.
Cioppino Holiday Food Drive
November 26th – December 15th
For their season of giving campaign, visit Cioppino between November 26th – December 15th make a non-perishable food donation + receive a $10 gift certificate toward a future visit!
Holiday Cookie Baking at Threadbare Cider
November 26
Join pastry chef Elise Miranda to bake some classic holiday cookies as well as some new favorites to add to your baking arsenal. Tickets includes a glass of cider, festive cookies to take home, and cheese, meat and pickle boards for nibbling while you make your cookies, as well as a tour of the Cider House!
Holiday m’Art
November 27-December 9
Stop by for creative gifts from unique artisans. Support Sweetwater Center for the Arts and shop for handcrafted wares from local and national artists. Holiday mART features a large selection of jewelry, ceramics, glass, fiber arts, two-dimensional art and much more!
TEDxPittsburghWomen 2018: Showing Up
November 29
This independently organized TEDx event will celebrate dynamic and diverse people who are showing up to face challenges head-on, all while empowering each other to shape the future we all want to see.
2018 Holiday Jam at The New Hazlett Theater
November 30
The 2018 Holiday Jam is a holiday concert features the original members of WQED:TV’s “Live From Studio A” band, the show features Pete Hewlett, Lisa Bleil and Scott Anderson, along with Eric DeFade, Benny Benack Jr., Joe Herndon, Bob Matchett, Steve Delach, Brian Stahurski and Joe Waslousky, along with special guests Maria Becomes-Bey and Benny Benack III.
Christmas Shopping Tour of the Little Shops of Butler County
November 30 – December 2
Have an adventure this holiday season and get to know the little shops of Butler County. The route travels from Butler to Portersville with 12 stops on the tour.
The Joy of Cookies: Cookie Tour 2018
November 30 – December 2
It’s almost time for a Pittsburgh holiday tradition! Visit 45 + unique businesses along Butler Street and Penn Avenue for holiday shopping and sample cookies. Collect recipe cards as you go to bake your own cookies.
Dashin’ Through The Bars Crawl
December 1
Get boozy and bright at this holiday-themed bar crawl. Dress in your holiday gear and crawl along the South Side. Tickets can be purchased online.
The Nightmare Before Christmas Brunch
December 1
The Oaks Theater is hosting a special brunch and movie screening for The Nightmare Before Christmas. See this movie on the big screen while enjoying a brunch provided by Oakmont Bakery.
Christmas Extravaganza at Vinoski Winery
December 1
It’s the most wine-derful time of the year! Enjoy Christmas cheer at Vinoski. More details to come on their Facebook page.
Pittsburgh Youth Chorus Winter Concert
December 2
The talented young singers of Pittsburgh Youth Chorus will perform their annual winter concert on Sunday, December 2 at the East Liberty Presbyterian Church. The audience is invited to sing along with traditional carols.
Taste of Lawrenceville: Miracle on 41st Street
December 2
This food-focused family event will celebration of all things Lawrenceville to ring in the holiday season. Enjoy breweries, restaurants, live music, kid’s activities, christmas tree sales, santa, shopping and more.
Holiday Cocktail Classes at The Fairmont
December 3
Andys’ cocktail specialists are hosting two classes where guests will learn how to make delicious and festive drinks for the holiday season.
Jazz Up The Holidays at August Wilson Center
December 3
It’s a jazzy way to celebrate the holidays. Billboard charting artist Lisa Ferraro will perform at the August Wilson Center. Proceeds benefit Familylinks and SoulCall. Tickets can be purchased online.
Holiday Printmaking Party at Ace Hotel
December 3
AIGA Pittsburgh, Workshop PGH, and Ace Hotel Pittsburgh are teaming up to host a printmaking party this holiday season. Local artists are sharing their original holiday designs which will be turned into screens for party-goers to screen-print on a variety of items. You will get to take home your creations. There will also be drinks and snacks. More information can be found online.
Holiday Lights Tour and Ugly Sweater Run with Pro Bike + Run
December 4
Run through downtown Pittsburgh and see the lights. Route runs through Market Square, The tree at Point State Park, The Nativity scene at US Steel Tower, and The PPG tree and rink. Come dressed in your holiday best and grab a drink at the Buckhead Saloon after. More information online.
Chanukah Festival 2018
December 4
Celebrate the first night of Chanukah at The Waterfront with the annual Chanukah Festival and Menorah Parade! Enjoy an outdoor concert, menorah lighting, food vendors, and games and activities for kids! The fun starts at 5:00 P.M.
Krampusnacht in Market Square
December 5
It’s not a Pittsburgh tradition to celebrate Krampus Night in Market Square. This ancient European holiday joins the merriment at the People’s Gas Holiday Market. Krampus will join St. Nicholas, and will hand out coal and the ruten bundles to bad children.  Follow Krampus in Pittsburgh for updates on the 2018 edition of this celebration.
Handmade Arcade
December 8
Shop local this holiday season! Handmade Arcade is one of Pittsburgh premiere artisan markets. Located in the David L. Lawrence Convention Center, hundreds of local vendors will be selling their goods.
Lunch with The Grinch at Uno Pizzeria & Grill
December 9
Enjoy a meet & greet with The Grinch while munching on a lunch of pizza, salad, sandwich, and wings.
Breakfast with Santa at the SouthSide Works
December 9
The annual Breakfast with Santa is happening on Sunday, December 9. Guests will be seated for breakfast at Hofbrauhaus and then SouthSide Works Cinema for pictures with Santa and goodie bags for the kids, followed by a special screening of Home Alone.
Wintermarket at Hotel Monaco
December 10-11
Shop locally made gifts from Pittsburgh area vendors, enjoy bites and cocktails from The Commoner, and listen to live holiday music at the Hotel Monaco second annual Wintermarket.
Hip Hop Nutcracker
December 11-12
A contemporary re-imagination of Tchaikovsky’s timeless music. Tickets and more information can be found online.
Holiday Crafts and Drafts at East End Brewing
December 15
Shop local artists and vendors for some last-minute holiday shopping, along with great food from La Palapa, Traditional Mexican Kitchen and desserts from Leona’s Ice Cream! More information can be found online.
Last Minute Shopping with I Made It! at The Block Northway
December 15
I Made It! Market is partnering with The Block Northway to bring a handmade shopping extravaganza in time for all of your holiday shopping. There will be 90+ local artisans, kids activities, food, and fun.
Made + Found Holiday Market
December 16
Made + Found returns to the Ace Hotel Pittsburgh for a special holiday market featuring 50 of the region’s most creative vintage and handmade vendors.
Free Holiday Concert at the Block Northway
December 16
Listen to some holiday music at the Block Northway and while holiday shopping at The Block at Northway.
WQED Cardigan Party
December 19
Take a walk down memory lane with Mister Rogers-themed music and entertainment and retro-themed snacks to celebrate the 50th Anniversary of Mister Roger’s Neighborhood in the very studio where “all the magic happened”. Cardigans & sneakers welcomed! More information online.
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