If you’re looking for proof that Pittsburgh never slows down, then we present to you the week of October 20-26 and all the events it holds. These adventures leave the city buzzing, offering a mix of experiences that will satisfy your craving for culture, fine dining, and pure entertainment. You can choose to spend an evening immersed in the powerful, masterful work of some of the country’s most vital performers. Or, you can step out for an exclusive, elevated culinary experience that honors a remarkable legacy. However, we wouldn’t blame you if you took the family-friendly route, choosing to celebrate the spooky season before October ends. It’s all waiting just right outside your door.
Pittsburgh Events Happening October 20-26
Sphinx Virtuosi with Cellist Sterling Elliott
October 21, Carnegie Music Hall
Lose yourself in the fierce talent of The Sphinx Virtuosi. This flagship ensemble of the Sphinx Organization is one of the most vital chamber orchestras of our time. Their 2025 program, Visions of Peace, explores resilience through music that reflects on conflicts past and present. Accompanied by cellist Sterling Elliott, the concert will feature works by Prokofiev and William Grant Still alongside premieres of newly commissioned pieces.
Uncle Nearest Whiskey Dinner at fl.2
October 23, fl.2
For those who want to expand their relationship with bourbon, this exclusive evening honors the legacy of Nathan “Nearest” Green. To celebrate the first known African American master distiller, guests enjoy a specially curated menu by Chef Canales. Each dish is thoughtfully paired with Uncle Nearest award-winning whiskeys for a dining experience that’s both delicious and historic.
Pumpkin Palooza: An East Liberty Halloween Adventure
October 25, Kelly Strayhorn Theater
Dress up the little ones and head out to spend the day inside the Kelly Strayhorn Theater to celebrate Halloween a few days early. Families can enjoy candy, crafts, and fun activities with community partners throughout the lobby. Plus, you won’t want to miss the performances from Hope Academy, Alumni Theater Company, K-Theatre Dance Complex, and Los Sabrosos’ Breakin’ for the Kids.
Clayton-Hamilton Jazz Orchestra
October 25, Manchester Craftsmen’s Guild
Experience the swinging sounds of the Clayton-Hamilton Jazz Orchestra at the Manchester Craftsmen’s Guild. Led by Grammy-winning bassist John Clayton and acclaimed drummer Jeff Hamilton, this big-band ensemble brings virtuosity, storytelling, and decades of jazz experience to the stage. Fans of big-band jazz will not want to miss this performance.
Rocky Horror Drag Brunch
October 26, Greer Cabaret Theater
‘Give yourself over to the absolute pleasure’ of the Rocky Horror Show by Pittsburgh CLO with a special drag brunch beforehand. Dixie Surewood and Chi Chi de Vivre present a pre-show party full of live drag performances, trivia, and giveaways. Throughout the show, guests will dine on a brunch food and cocktail menu that’ll leave them in antici-…pation for more.
Story by Kylie Thomas
Featured Photo Courtesy of Uncle Nearest Premium Whiskey
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