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Event Name: Over & Under: A Stranger Things-Inspired Pop-Up BarDate: Friday, November 21, 2025 – Saturday, February 28, 2026Location: City Kitchen Patio at Bakery Square, 145 Bakery Square Blvd, Pittsburgh, PA 15206Category: Food + BeverageCost: Free Details:Something strange is brewing in Hawkins—and it’s closer than you think. Bakery Square transforms into a Stranger Things-inspired world for Over & Under, a Read more...
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November 21, 2025, 10:00 am
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January 4, 2026, 6:00 pm
Address: 4800 Kennywood Boulevard
15122
15122
Kennywood Holiday Lights Kennywood, November 14 – January 4 There’s always something seasonal happening at Kennywood, and the holidays are no exception. It’s perfect as a family outing, or as a fun solo date to get into the Christmas spirit. You’re never too old to make a Build-a-Bear or send a letter to Santa. Find more information here! Find more Read more...
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DiAnoia’s Holiday Celebrations Locations: DiAnoia’s Eatery & Pane è Pronto, Strip District, Pittsburgh Seasonal Offerings: Available December 9 – 23, 2025 DiAnoia’s Eatery and its sister shop, Pane è Pronto, celebrate the holidays with an array of Italian specialties, from a traditional seafood feast to festive sweets and pantry staples. Feast of the Seven Fishes at DiAnoia’s Eatery A beloved prix-fixe, family-style Read more...
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IZABELLA’S GOURMET CHOW: FALL COOKING CLASSES & EVENTSVarious Dates, October–December Chef Sofya and Izabella’s Gourmet Chow are serving up a season full of hands-on classes and festive gatherings for kids and adults. Children’s classes ($35, ages 4+) combine cooking with lessons in language, culture, and dance. Highlights include Italian arancini with cheese sauce on October 6, 14, and 15, and Read more...
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Home Alone Inspired Cocktail Class with Tipsy Wheels Event: Home Alone Inspired Cocktail Class Host: Carina Victor & Tipsy Wheels Date & Time: Wednesday, December 17, 2025, from 6:00 PM to 9:00 PM (Doors open at 5:45 PM) Location: 5549 Old William Penn Highway, Suite 300, Murrysville, PA 15668 Admission: Ticketed (Ages 21+) Good to Know: In-person, 3-hour event. This event has a no-refund policy. Keep Read more...
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Event: Christmas Cocktails Workshop Pt.1 Host: The PA Market Date & Time: Wednesday, December 17-18, 2025, from 6:30 PM to 8:00 PM Location: The Pennsylvania Market, 108 19th St, Pittsburgh, PA 15222 Admission: Ticketed (Ages 21+) Good to Know: In-person, 90-minute workshop. This event has a no-refund policy. Get in the holiday spirit! The popular Christmas Cocktails workshop is back for another festive year at The PA Read more...
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The Cheer You Deserve with Woodford Reserve Event: The Cheer You Deserve with Woodford Reserve Host: Renaissance Pittsburgh Hotel Date & Time: Wednesday, December 17, 2025, from 6:30 PM to 8:30 PM Location: Renaissance Pittsburgh Hotel, 107 6th St, Pittsburgh, PA 15222 Admission: Ticketed Good to Know: This is a 2-hour, in-person tasting event. Refunds are available up to 7 days prior. Step into an evening Read more...
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Christmas Movie Trivia Bakery Square, December 18 If you’re a Christmas movie wiz, this is the event for you. Grab some sips and bites from City Kitchen and make sure you know your Frosty the Snowman, It’s a Wonderful Life, or maybe even Die Hard fun facts. Find more information here! Find more events going on in Pittsburgh here! Read more...
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Mystery after Dark: A Culinary Whodunit at The Commoner December 19, 2025–January 4, 2026 The Commoner introduces an immersive Clue-inspired dining experience this winter. The three-course prix fixe dinner invites guests to become detectives for the evening, using an Investigator’s Journal to meet suspects, uncover secrets, and solve the disappearance of the chef’s prized recipe binder. Diners who crack the Read more...
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Shorty’s Santa ShopNow through December 30, 2025Shorty’s North Shore & Shorty’s Waterfront Shorty’s Santa Shop is back for its second season—and bigger, brighter, and more festive than ever. Both Shorty’s locations have transformed into full North Pole-inspired wonderlands. They are complete with thousands of twinkling lights, themed rooms, and immersive holiday photo ops. Guests can wander through Candy Cane Lane, Read more...