Winter Wonderland
Cupka’s Cafe 2. 2314 E. Carson St., South Side.
facebook.com/Cupkascafe2
Cupka's Cafe 2 will make spirits brighter than usual in the South Side with its big holiday Winter Wonderland pop-up. Revelers are encouraged to stop in for signature cocktails, craft beers, and daily specials, all in a festive atmosphere complete with tons of lights, decorated trees, and more. Even better, proceeds from Winter Wonderland sales benefit the South Side Kids Free Breakfast with Santa — taking place on Sat, Dec. 16, the event invites local youth in need to enjoy toys, games, and other fun activities, as well as meet the big man himself. Sippin' Santa
490 Wood St., Downtown. sippinsantapopup.com
It's July in Christmas at Sippin' Santa, a happy hour pop-up bar from the same people behind the popular Miracle concept. From now through the end of December, head to 490 Wood St. between Capital Grille and McCormick & Schmick’s for tiki-themed cocktails and island-inspired decor meant to evoke a holiday in the tropics (one Instagram post describes the vibe as "Santa on a tropical vacation.") 
CP photo: Jared Wickerham
Inside Miracle on Liberty
Miracle on 6th
137 Sixth St., Downtown. instagram.com/miraclepgh
Speaking of Miracle, it's back and just as festive as ever. All through December, the temporary bar welcomes patrons every day from 4 p.m. until midnight for seasonal drinks like the Snowball Old Fashioned and Rudolph’s Replacement, described as a "tasty coffee cocktail." Enjoy both Christmas and Hanukkah decor while helping organizers raise money for good causes (a portion of Miracle on 6th sales will go to local charities). Winter Warmer
Square Cafe. 134 S. Highland Ave., East Liberty. square-cafe.com
East Liberty will get a whole lot cozier this season with the Winter Warmer pop-up at Square Cafe. Every Friday through Sunday through the end of January 2024, the popular brunch-centric spot welcomes customers to enjoy festive decor, cocktails, and warm drinks while waiting for a table. The pop-up menu features a variety of seasonal lattes, as well as spiked or non-spiked hot chocolate and mocktails, with many drinks being offered on a rotating basis.
Home Alone Christmas Pop-Up Bar
Barcadia. 24 Market Square, Downtown. barcadiapgh.com
Drink up, you filthy animals — Barcadia has a truly inspired concept perfect for you and your crew of Wet Bandits. Based on the hit 1990 family comedy and its 1992 sequel, the Home Alone pop-up bar brings some holiday cheer to the adult arcade, where, from now through Jan. 1, 2024, guests can sip wintery cocktails while playing pinball and other classic games.Rudolph's Rooftop Holiday Pop-Up Bar
Sienna Mercato. 942 Penn Ave., Downtown. siennamercato.com
Up on the rooftop at Sienna Mercato awaits a wonderland inspired by one of Santa's most dedicated reindeer. Head up to the Il Tetto Rooftop Beer Garden from now until New Year's Eve for what the event page describes as a "Rudolph-themed winter cocktail menu" that includes Cornelius's Snowcap (a blend of vanilla, Kahlua, coffee, and caramel) and Dasher's Cinnful Kentucky Mule (Maker's Mark mixed with cinnamon, lime, and ginger beer), as well as many others. The Iron City and I.C. Light Good Cheer Holiday Bar Takeover
Rugger's Pub. 40 S. 22nd St., South Side. ruggerspub.com
It doesn't get more Pittsburgh than this. Rugger's Pub combined forces with a local beer brand to create what's being dubbed the "official holiday bar" of Iron City and I.C. Light. The menu includes Iron City specials, as well as a number of seasonal cocktails, shots, and other goodies. Tinseltown: The Christmas Speakeasy
Mixtape. 4907 Penn Ave., Garfield. mixtapepgh.com
A local bar and dance club has converted into a holly jolly hangout with help from The Viral Group. Head to Mixtape from now through Sat., Dec. 30 to experience Tinseltown (formerly Tipsy Elf), a ticketed event described in a press release as bringing "Santa's elves, tinsel, festive tunes and lots of winter warmer drinks, including a fabulous custom-created Christmas cocktail menu" to Penn Avenue. Non-alcoholic drinks are also available upon request. Tinseltown weekday sessions are available Wednesday-Friday from 5:30-11 p.m., and weekend sessions run Saturday from 11 a.m.-10:30 p.m. and Sunday from 11 a.m.-8:30 p.m. Family-friendly sessions are also available to accommodate under-21 friends and family members. (The Viral Group is affiliated with Hidden Media Network, a company Pittsburgh City Paper covered back in 2021. The company is separate from Mixtape, which only serves as a host venue.)
