Hi there! Here’s your hand-picked list of Pittsburgh happenings for the upcoming long stretch—from Friday, Sept 19 through Sunday, Sept 28, 2025. Have fun out there!
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
$14.99 Friday Night Special at Mattress Factory
Dates: Fri, Sept 19, 5–8 pm • Location: Mattress Factory, 500 Sampsonia Way (North Side)
Community night with live music + museum admission for just $14.99. Cost: $14.99 GA (free for members). Presented by: Mattress Factory. More Info
Pittsburgh Art Book Fair
Dates: Sept 20–21 • Location: Carnegie Museum of Art, Hall of Sculpture (Oakland/East End)
Zines, art books, and indie presses galore—free and open to all. Cost: Free. Presented by: Carnegie Museum of Art & PABF. More Info
“Transformation 12: Contemporary Works in Wood” – Opening Reception
Date: Fri, Sept 19, 5:30–8 pm • Location: Contemporary Craft, 5645 Butler St (Lawrenceville)
Kick off a major craft exhibition celebrating innovative wood art. Cost: Free. Presented by: Contemporary Craft. 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
Lawrenceville Farmers Market
Date: Tue, Sept 23, 3–7 pm • Location: Bay 41, 4107 Willow St (Lawrenceville)
Peak-season produce, baked goods, and community vibes. Cost: Free entry; vendors for purchase. Presented by: Lawrenceville United. More Info
Warhol Museum – Good Fridays (Open Late)
Dates: Fri, Sept 19 & Fri, Sept 26 (open late to 10 pm; half-price after 5 pm) • Location: 117 Sandusky St (North Shore/North Side) More Info
Explore Warhol after hours at a discount. Cost: Half-price after 5 pm. Presented by: The Andy Warhol Museum.
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
Pittsburgh Glass Center – “Gather & Brew” Make-It-Now
Date: Fri, Sept 19, 5 pm • Location: 5472 Penn Ave (Garfield/East End)
Sip and try your hand at hot glass with instructor guidance. Cost: Ticketed. Presented by: Pittsburgh Glass Center. 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
Bakery Square Live Music (Outdoor)
Date: Sat, Sept 20, 6–9 pm • Location: Bakery Square, 6425 Penn Ave (East Liberty/Larimer)
Free, family-friendly tunes on the lawn—bring a chair or blanket. Cost: Free. Presented by: Bakery Square. 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
The Frick Pittsburgh – “Catching Sunbeams: A Study in Brilliant Color”
Dates: Ongoing (open during the week) • Location: The Frick, 7227 Reynolds St (Point Breeze/East End)
A shimmering greenhouse installation you can stroll during museum hours. Cost: Free. Presented by: The Frick Pittsburgh. More Info
Bloomfield Saturday Market
Date: Sat, Sept 20, 9 am–1 pm • Location: 5050 Liberty Ave (Bloomfield)
Beloved neighborhood market with produce, makers, and music. Cost: Free entry; vendors for purchase. Presented by: Bloomfield Development. More Info
National Aviary – Friends of the Flock Champagne Brunch: Birds & Bubbly! (21+)
Date: Sun, Sept 21, 11 am • Location: National Aviary (North Side)
A fancy fall brunch in the Garden Room—cheers! Cost: $78 per person. Presented by: National Aviary Friends of the Flock. More Info
Enjoy! Crisp nights + bright days = perfect for biergartens, book fairs, and chrysanthemum strolls. And mark your calendar a little farther out: Festival of Combustion fires up at the Carrie Blast Furnaces on Sat, Oct 4—a great way to explore one of the region’s most iconic industrial sites (very architecture/real-estate-nerd friendly!).
