Hi there! Here’s your hand-picked guide for the long stretch ahead — events for Sept 26 – Oct 3, 2025. Dive into arts, culture, family fun, food, and all the fall feels!
Penn Brewery Oktoberfest
Dates: Sept 19–21 & Sept 26–28 • Location: Penn Brewery, 800 Vinial St (Troy Hill/North Side)
Classic biergarten vibes, oompah bands, German eats, and family Sunday fun. Cost: Free admission; food/drink for purchase (VIP upgrades available). Presented by: Penn Brewery. More Info
Pittsburgh Brewing Co. Oktoberfest (East Deer)
Sat, Sept 27 • Pittsburgh Brewing Co., East Deer • One-day Oktoberfest with bands, German fare, and special releases. Cost: Free entry; food/drink for purchase. Presented by Pittsburgh Brewing Company. More Info
Squirrel Hill Night Market
Date: Sat, Sept 27, 6–10 pm • Location: Murray Ave (Squirrel Hill)
Outdoor evening market with artists, makers, music, and food. Cost: Free entry; vendors for purchase. Presented by: Uncover Squirrel Hill. More Info
Pittsburgh Dragon Boat Festival
Date: Sat, Sept 27, 8 am–3 pm • Location: North Park Lake (North Hills)
Cheer on dragon boat races and enjoy cultural demos and vendors. Cost: Free to attend. Presented by: Pittsburgh Dragon Boat Festival. More Info
Phipps Conservatory – Chrysanthemum Night
Date: Fri, Sept 26, 6:30–10 pm • Location: Phipps Conservatory (Oakland)
A one-night glow-up for fall florals; first 300 members receive a complimentary chrysanthemum. Cost: Included with membership (check details). Presented by: Phipps Conservatory. More Info
The Frick Pittsburgh — “The Scandinavian Home: Landscape & Lore” (Exhibition Opening)
Opens Sat, Sept 27 • The Frick, Point Breeze (East End) • New exhibition exploring Nordic myth and domestic design. Cost: Ticketed; check site. Presented by The Frick Pittsburgh. More Info
Kelly Strayhorn Theater — David Roussève/REALITY: Becoming Daddy AF
Fri–Sat, Sept 26–27, 7:30–9:10 pm • KST, East Liberty (East End) • World-premiere dance theater; Pay-What-Moves-You. Cost: $20–$35. Presented by Kelly Strayhorn Theater. More Info
Pittsburgh Glass Center – Art on Fire Celebration + Auction
Date: Fri, Sept 26, 6 pm • Location: Pittsburgh Glass Center (Garfield/East End)
The hot party + glass auction that supports PGC. Cost: Ticketed benefit. Presented by: Pittsburgh Glass Center. More Info
Kennywood — Phantom Fall Fest (select dates)
Sept 26–28 & Oct 3 • Kennywood, West Mifflin (easy from East/North) • Daytime family fun; after dark, haunted houses and scare zones. Cost: Ticketed. Presented by Kennywood. More Info
Allegheny County Hay Day (South Park)
Sat, Sept 27, 11 am–3 pm • South Park (Countywide favorite) • Free fall festival with family activities, entertainment, and treats. Cost: Free. Presented by Allegheny County Parks. More Info
Pittsburgh Renaissance Festival — Final Weekend
Sept 27–28, 10:30 am–6:30 pm • West Newton (East Suburbs) • Jousting, crafts, eats — last chance this season. Cost: Ticketed. Presented by Pittsburgh Renaissance Festival. More Info
Have a fantastic weekend and week ahead! Cooler evenings, twinkle lights, and that first hint of woodsmoke pair perfectly with night markets, Oktoberfest tents, and crisp laps around North Park Lake. Keep an eye on October’s calendar, too — architect- and real-estate-lovers will want to catch DOORS OPEN Pittsburgh for behind-the-scenes peeks inside landmark buildings. If that kind of home-tour energy gets you curious about buying, selling, or just getting market-smart, I’m always here to help you plan the next move.
