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South Side Winterfest December 6 • 3–7 PM + Santa Stroll 7–10 PM • Bedford Square, Esser Plaza & 12th Street • Free The South Side debuts a brand-new neighborhood celebration this year with South Side Winterfest. This is a lively, all-ages festival bringing together artists, makers, musicians, and local businesses for an afternoon of holiday cheer. The event features Read more...
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Oz Dust Ball Pittsburgh Step into a world of magic, music, and glamour at the Oz Dust Ball, coming to Pittsburgh on December 6. Date and timeSaturday, December 6 · 7–11 pm EST. Doors at 6:45 pm LocationSoldiers & Sailors Memorial Hall & Museum4141 Fifth Avenue #3rd FloorPittsburgh, PA 15213Get directions Good to knowHighlights 4 hours Ages 21+ In person Read more...
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Steelers Watch Party Series at Pittsburgh Brewing Company Tap RoomEvery Steelers Game Day · Times VaryPittsburgh Brewing Company Tap Room, Creighton Pittsburgh Brewing Company keeps the black-and-gold spirit alive all season long with its Steelers Watch Party Series at the Tap Room. Fans can catch every home and away game on big-screen TVs in a lively, family-friendly atmosphere. Enjoy flagship Read more...
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Cookies with Santa Claus Sunday, December 7 | Seating 10 AMJoin Santa in the Grand Ballroom for a cheerful morning of cookie decorating, crafts, and festive dining. Includes a brunch buffet, photo with Santa, and a take-home cookie kit.Tickets: $70 Adults | $50 Children (plus tax and fees) Find more information here! Find more events going on in Pittsburgh here! Read more...
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Jazz Magic: A Family Affair Album Party Sunday, December 7 | 6 PMCelebrate jazz across generations as Esai Aliquo-Varela and her grandfather, sax legend Don Aliquo Sr., host a fundraising concert and variety show for their new EP. Featuring Phat Man Dee, Viva Valezz, and other local talents, this evening supports Pittsburgh’s musical legacy.Tickets: $20 (benefits the Aliquo Family EP 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...