★ Pittsburgh Public Schools 5K + Wellness Social
5K race followed by a free wellness social with cold plunges, saunas, yoga, food trucks, and coffee carts at Obama Academy; use code YINZ for 15% off registration.
17 Things to Do in Pittsburgh This Week · August 27–30, 2026
Top Picks This Week
Music & Nightlife
Jazz in the Garden
Live jazz performance in the lush garden setting of Phipps Conservatory, a perfect late-summer evening outing.
Thursday, August 27, 2026 · Phipps Conservatory, Oakland
| Pittsburgh CityPodcast – Daily Events | CalShare |
Celestial Bodies: Virgo SZN
Open-format dance party where every track is by a Virgo artist, featuring DJs Lemonline and Paula Jean plus a drag performance by Aunt Honey.
Friday, August 28, 2026 10:00 PM · Spirit, Lawrenceville
| @arcane.city | CalShare |
Sierra Ferrell: Heavy Petal Tour
Sierra Ferrell and The Brudi Brothers bring her acclaimed country-folk sound to the Stage AE outdoor stage.
Tuesday, September 1, 2026 6:00 PM · Stage AE, Pittsburgh
| Stage AE / PromoWest – Pittsburgh Calendar | CalShare |
An Acoustic Evening with The Spill Canvas
Intimate acoustic performance from The Spill Canvas at City Winery Pittsburgh in the Strip District.
Wednesday, September 9, 2026 · City Winery Pittsburgh, Strip District
| City Winery Pittsburgh – Events | CalShare |
Arts & Culture
Mark Normand at Bottlerocket
Stand-up comedian Mark Normand performs an early Thursday show at Bottlerocket Social Hall in Allentown.
Thursday, August 27, 2026 · Bottlerocket Social Hall, Allentown
| Pittsburgh CityPodcast – Daily Events | CalShare |
Jibz Cameron / Dynasty Handbag: Hell in a Handbag
Free performance art event featuring Jibz Cameron / Dynasty Handbag at SPACE Gallery in the Cultural District.
Friday, August 28, 2026 · SPACE Gallery, Downtown Pittsburgh
| Pittsburgh Cultural District – Trust Arts Calendar | CalShare |
Free Events
Pickleball with PUMP
Free outdoor pickleball sessions at Arts Landing in the Cultural District, hosted by Pittsburgh Cultural Trust and PUMP.
Thursday, August 27, 2026 · Arts Landing, Downtown Pittsburgh
| Pittsburgh Cultural District – Trust Arts Calendar | CalShare |
Summer Fridays at the Frick
Late summer evening at The Frick Pittsburgh with extended hours to explore the art and grounds in Point Breeze.
Friday, August 28, 2026 · The Frick Pittsburgh, Point Breeze
| Pittsburgh CityPodcast – Daily Events | CalShare |
Open Up Pittsburgh Dance Party
Monthly inclusive community dance party at Open Up's Butler Street studio, welcoming all bodies and abilities.
Friday, August 28, 2026 7:00 PM · Open Up, 3711 Butler St., Pittsburgh
| @openuppgh | CalShare |
Summer Concert Series Final Weekend – City of Pittsburgh
The final weekend of the 2026 Summer Concert Series presented by Citizens featuring local Pittsburgh talent at the reservoir.
Saturday, August 29, 2026 · Highland Park Reservoir, Pittsburgh
| @pgheventsoffice | CalShare |
Festivals & Special Events
Pittsburgh Renaissance Festival
Six weekends of jousting, live entertainment, medieval games, artisan shopping, and festival food running Saturdays and Sundays through September 27 in West Newton.
Saturday, August 29, 2026 · West Newton, Pennsylvania
| @belocalpittsburgh | CalShare |
Spirit Summer Recess 2026
All-day outdoor music festival at Spirit featuring live performances by Frankie & The Witch Fingers, King Blue Heron, Sunny Daze & The Weathermen, and more, with a 21+ afterparty indoors.
Saturday, August 29, 2026 2:00 PM · Spirit, Lawrenceville
| @pghcitypaper | CalShare |
Outdoors & Active
Date Night
Lip Sync Battle Drag Brunch at Velum Fermentation
Drag brunch with a competitive lip sync battle format at Velum Fermentation, doors at 11 AM and show at noon.
Saturday, August 29, 2026 11:00 AM · Velum Fermentation, 2120 Jane St, Pittsburgh
| @ssproductionspgh | CalShare |
Alex Marley at City Winery Pittsburgh
Live music from Alex Marley in the intimate dinner-and-show setting of City Winery in the Strip District.
Monday, August 31, 2026 · City Winery Pittsburgh, Strip District
| City Winery Pittsburgh – Events | CalShare |
Pittsburgh Speed Dating for Singles Age 30s/40s
Speed dating event for singles in their 30s and 40s at Doce Taqueria in Bridgeville.
Saturday, September 5, 2026 7:00 PM · Doce Taqueria, Bridgeville
| Eventbrite Pittsburgh – Home & Lifestyle | CalShare |
Family-Friendly
Movie Night Marketplace with I Made It! Market at Bakery Square
Outdoor movie night market with local small businesses, vintage collectors, and artists at Bakery Square.
Sunday, August 30, 2026 5:00 PM · Bakery Square, Pittsburgh
| I Made It! Market – Event Calendar | CalShare |