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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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Winter Wines & Dessert Pairings Event: Winter Wines & Dessert Pairings Host: The PA Market Date & Time: Wednesday, December 10, 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: This is a 90-minute, in-person class with free parking. Please note, there is a no-refund policy. Celebrate the magic of December 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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Cozy Cocktails Workshop Host: The PA Market Date & Time: Thursday, December 11, 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. Beat the winter chill and learn to craft delicious hot cocktails! Join The PA Market for a Cozy Cocktails workshop where you’ll sip Read more...
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Annual Disco Cowgirl Christmas Market Bella Terra Vineyards, December 12 Enjoy a fun, flirty take on a holiday market with a country flair at this beautiful boutique winery at Hunker, just 45 minutes outside of Pittsburgh. On theme with the winery’s monthly Country Wine Dancing event, this holiday market promises to have rhinestone cowgirl vibes. Find more information here! Find 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...
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December 13, 2025, 10:30 am
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3:00 pm
Address: Washington Pike, Kirwan Heights, Collier Township
15017
15017
Breakfast with Santa Event: Breakfast with Santa: Complimentary BYO Hot Cocoa Bar & Cookie Decorating Host: Doce Taqueria Date & Time: Saturday, December 13, 2025, from 10:30 AM to 3:00 PM Location: Doce Taqueria Bridgeville, 1025 Washington Pike #unit 240, Bridgeville, PA 15017 Admission: Ticketed (All Ages) Good to Know: In-person, 4.5-hour event. Doors open at 10:30 AM. Refunds available up to 7 days before the Read more...
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Holiday Community Day AWAACC Friday, December 13 | 12–4 PMAugust Wilson African American Cultural Center, 980 Liberty Ave., PittsburghFree Admission Celebrate the season with an afternoon of joy, culture, and community at AWAACC’s annual Holiday Community Day. The free, family-friendly event features live music and dance, photos with Santa and Mrs. Claus, a Kwanzaa drumming and dance performance by Opoku Read more...
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Whiskey and Chocolate PairingSaturday, December 13, 2025 | 3:30–5 PMIron City Distilling, 150 Ferry Street #Bldg 2, Creighton, PA Details:Savor the perfect balance of bold and sweet at Iron City Distilling’s Whiskey and Chocolate Pairing. Each pour of handcrafted whiskey will be paired with artisan chocolates from Valos Chocolates, creating a decadent tasting journey. Guests can enjoy lounge-style seating on Read more...