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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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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...
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Uncover Squirrel Hill Holiday Wine Walk Squirrel Hill, Forbes & Murray AvenuesDecember 13, 4–7 PM Sip your way through Squirrel Hill at this annual self-paced wine-tasting stroll. The Holiday Wine Walk invites guests to explore the neighborhood’s business district while sampling approximately 15 wines and unlocking exclusive discounts from participating shops along Forbes and Murray. Check-in begins at 5884 Forbes Read more...
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Chunky Knit Snowman Workshop & Hot Chocolate Bar Host: Hampton Inn Greensburg Date & Time: Multiple Dates Available Category: Holiday, Christmas Overview: Get cozy for the craft night of the season! Create your own adorable, super-soft chunky knit snowman and enjoy a festive hot chocolate bar. Join the Hampton Inn Greensburg for a cozy and creative holiday workshop. You’ll craft your own adorable Chunky Read more...
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Cookies and Cocoa with Santa Host: A&N Garden and Greenhouse Date: Saturday, December 14, 2025 Available Time Slots: 1:00-1:30 PM, 1:30-2:00 PM, 2:00-2:30 PM, 2:30-3:00 PM Location: A&N Garden and Greenhouse, 2130 Reis Run Road, Pittsburgh, PA 15237 Admission: $25.00 per child (Adults attend free; tickets not required for adults) Good to Know: This is an in-person event for children with a parent or guardian. Free Read more...
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Letters to Santa – Kids Christmas Workshop Host: Green Heiress Retreats Date & Time: Sunday, December 14, 2025, from 2:00 PM to 4:00 PM (Doors open at 1:50 PM) Location: Green Heiress Holistic Health, 209 Commercial Avenue, First Floor Studio, Aspinwall, PA 15215 Admission: Ticketed (Ages 5–12; parent or guardian must accompany child) Good to Know: This is a 2-hour, in-person workshop with a no-refund Read more...