Your Holiday Hit List

The holiday list you have all been waiting for … 

Ok, or maybe just me. But is there anything better than seeing Pittsburgh in the spirit? Lights, hot cocoa, drunk Santa’s and everything in between.

Here is your official December event round up (and growing!!)

Boozy Experiences

Wicks and Sips, December 2, 6:00pm

BrewDog and PGH Candle collab: a pre-determined flight (5 6oz. pours), your candle creation, and 5% off your food bill! Tickets are $30 each or $55 per couple. More info.

Get Lit at Inner Groove, December 8, 5:00pm

Santa is coming! Enjoy holiday beers, live music, BBQ and the big guy in red himself at Inner Groove Brewing. More info.

11th Hour Brewing Ugly Sweater Party, December 11, 7:30pm

More info to come.

Fire Fest, December 11, 12:00pm

Ten fire pits. Can releases. Holiday 6-pack. Food trucks, Specialty Cocktails. More info to come from Grist House in Millvale.

Squirrel Hill Wine Walk, December 11, 4:00pm

Join Uncover Squirrel Hill for our Annual Holiday Wine Walk: a self-paced wine tasting experience. Enjoy approximately 15 different wines and exclusive discounts at participating host Merchants. Tickets are $30. More info.

Sip, Taste & Build – SOLD OUT, December 15, 6:30pm

Join Olive the Cheddar Boards at Altared Genius and learn how to build a holiday themed charcuterie board to take home! Tickets are $45.

The Roaring 2020s Soiree, December 17, 6:00pm

Heading to Cinderlands Foederhouse to ring in the New Year a little early with live DJ, dancing, fancy clothes and a special mone. Plus beer. Gatsby clothes encouraged. Tickets start at $35. More info.

The Night Before Krampus, a Festive Ale Festival, December 17 at 6:00pm

Join Necromancer Brewing for a night of enjoying all of the best local holidays brews Pittsburgh has to offer under one roof before they’re gone until next year. DJ and prizes included. Tickets are $45. More info.

Leaning Cask Ugly Sweater Party, December 18, 12:00pm

Holiday specials, prizes and of course … lots of beer and ugly sweaters. More info.

Pop Up Bars



Paint Your Own Pottery Night – SOLD OUT, December 1 and December 8, 6:00pm

In these 2-hour workshops at Threadbare Cider House in partnership with Little House, Big Art, guests will glaze their own one-of-a-kind, ceramic marbled mug! Support a local, woman owned small business and get crafty while you’re at it. Tickets are $30. More info.

Northside Glow Opening Night, December 4 from 3:00 – 7:00pm

The ceremonious kick off event for a beautiful light display in Allegheny Commons East Park! More info

Ben Avon Holiday House Tour, December 4 from 10:00am – 4:00pm

Seven beautiful homes in the Ben Avon Borough, all beautifully decorated for the holidays. The homes chosen each represent a wide variety of architectural styles and designs, as well as diversity in age of the home. Advance Tour Tickets: $25 Day, $30 Candelight. More info

A Creepy Christmas: The Scarehouse, Christmas Edition

A twisted tale of holiday horror for two weekends only: Friday & Saturday Night 12/10 , 12/11 – 12/17. 12/18. Tickets starting at $20. More info.

Christmas Cookies and Wine Tasting, December 9 or 22 at 6:00pm

Following a tour of Narcissi Winery will be an in depth explanation of the wine making process and extensive tasting of 6 wines. Each will be paired with fabulous traditional Christmas cookies from the Oakmont Bakery. Tickets are $45. More info.

DIY Holiday Ornament Workshop, December 9, 5:45pm

AR Workshop’s team will be at Cadence Clubhouse in North Park helping you make your very own set of wood sliced ornaments. Tickets start at $39.50 for 6 ornaments and include a $10 gift card towards food or drink. More info.

Soup and Wine, December 9, 6:00pm

Join Brothmonger at Refucilo Winery in the North Side for a soup and wine pairing event. Tickets are $34.50. RSVP by 12/5 by calling 412-251-0251.

Jazz Dinner: Don Aliquo and Friends, December 9, 6:30pm

Enjoy an intimate, multi-course Italian dinner at Sprezzatura with live jazz featuring the sounds of Don Aliquo and his quartet. Tickets are $40. BYOB. More info.

It’s a Wonderful Life Wine Tasting, December 16, 7:00pm

Head to The Oaks Theater to watch holiday classic It’s a Wonderful Life, enjoying a wine tasting prior to the film. General Admission $8. More info

Wine Dinner, NATALE ITALIANO, December 16 at 6:30pm

A 4 course dinner at Narcisi Winery featuring original Italian recipes, each paired with Narcisi wines. Tickets are $85. More info

Ugly Sweater Christmas Party, December 17, 8:00pm

Head to Barry’s Pub in McCandless for their insane Christmas decor, DJ and food/drink specials. Free entry.

Mexican War Streets Winter Wonderland Extravaganza, December 18, 5:00pm

Tonight, enjoy walking around our streets seeing magical lights, decorations, say hello to neighbors, and stop to enjoy the history! More info.

Dickens Dinner, December 21, 22 and 23, 6:30pm

This Hyeholde dinner menu will honor the period of Dickens’ works and actors from Laura Young and Co. will bring scenes from “A Christmas Carol” to life throughout the halls. Tickets are $125, drinks not included. More info.


Holiday Markets

People’s Gas Holiday Market, November 19-December 23

Shop from more vendors than ever before as you stroll through an illuminated Market Square at the tenth annual Peoples Gas Holiday Market™, weaving through wooden chalets brimming with high-quality gifts and holiday experiences uniquely filled with international flair and local charm. More info.

Krampus, Baby, December 1-23

A monthlong holiday pop-up in the Lorelei cocktail bar, with an all-new menu of wintry cocktails to warm your bellies — and your spirits. This will operate Wed-Sat, 5-10 p.m. to start. The full food menu from @woodfiredpgh and full draft and wine lists will also be available in the cocktail bar. No reservations are needed! 

Workshop Holiday Pop Up, December 3, 10am

10 local makers all joining at one single studio, along with some mini wreath making fun? Count me in. More info.

Holiday Mart at Sweetwater Center for the Arts, December 3-12

Holiday Mart is the Sweetwater annual pop-up boutique of artist-made gifts! Shoppers will find a wide variety of jewelry, ceramics, glass, weavings and knitwear, fine art, ornaments, cards, edibles & so much more. More info.

Handmade Arcade, December 3 and 4

So much more than just a market, this holiday extravaganza at the David L. Lawrence Convention Center celebrates our region’s art and culture with everything from live glass blowing demonstrations to free grab-and-go craft kits. More info.

Cinder Bell Rock – SOLD OUTDecember 9, 4:00pm

A night of live jazz, shopping small and local for gifts, and lots of good cheer. Cinderlands will have their entire space decked out as a winter wonderland. Think re-imagined, modern, and beer-focused German night market. More info.

Winter Artisans Market, December 11, 10:00am

A day of art and cheer to help warm you into the holiday season. More info.

Threadbare Winter Market, December 11, 11:00am

Celebrate the Holiday Season at Threadbare Cider House’s annual Winter Market. Local artisans will be selling their wares in the Cider Cellar. Kids can decorate a holiday ornament while adults sip Cider and get all of their holiday shopping done. More info.

Crafts & DraftsDecember 12, 12:00pm

Head to East End Brewing where there’s a full lineup on deck of local artists, makers, and vintage that will be hanging out on the patio with fire pits and live music. More info.

Made & Found Holiday Market, December 19, 11:00am 

Made & Found is back with a holiday market at Spirit showcasing the region’s best vintage shops, makers, and small brands. More info.

Family Friendly

Sewickley Light Up Night, December 3, 5:00pm

Fun for the whole family featuring a spectacular fireworks show sponsored by ESMARK, live music by members of The Clarks as well as Allegheny Brass Band, community performances, free horse drawn carriage rides sponsored by First National Bank, live reindeer sponsored by Village Works, ice carving sponsored by The Stehnach Group & The Sewickley Confectionary, food vendors and more… More info.

Santa at The Terminal, December 2-24, 12:30pm – 5:00pm

Find Santa in the Red Passageway at 17th Street of the Strip District Terminal to get those beloved photos with Santa! Hours vary, so reserve your time slot. Book here

Winter Solstice Lantern Walk, December 18, 5:00pm

In celebration of the Winter Solstice, the longest night of the year, the Fox Chapel Parks Conservancy will illuminate the trail at charming Salamander Park with candlelight on Saturday, December 18, 2021. Enjoy a complimentary steaming cup of hot chocolate. More info.

That’s a wrap! Check back … I’ll be updating this periodically. But the best place for links and details? “december” highlight on @thepittsburghweb.



Loves wine, whiskey and pretending to be a sophisticated foodie. Also really loves Pittsburgh.