15 Things to Do in Pittsburgh This Week · May 14–17, 2026

Festivals & Special Events

Millvale Music Festival

Annual multi-day music festival in Millvale featuring live performances, public art mosaic-making, and community celebration across the borough.

Friday, May 15 – Saturday, May 16, 2026 · Millvale

Music & Nightlife

Black Veil Brides: North American Tour 2026

Black Veil Brides headline an indoor rock show at Stage AE with support from From Ashes To New, TX2, and As December Falls.

Friday, May 15, 2026 5:30 PM · Stage AE, Pittsburgh, PA

Live Music at Helltown Brewing with PGH Social Club

Pittsburgh Social Club hosts a night of live music at Helltown Brewing in the Strip District with outdoor patio access and drink specials.

Saturday, May 16, 2026 8:00 PM · Helltown Brewing, Strip District

Afro-Caribbean Third Saturdays: FLAGZ & WAISTLINES

A monthly Afro-Caribbean dance party at Spirit Lodge celebrating Caribbean rhythms, dancing, and community.

Saturday, May 16, 2026 10:00 PM · Spirit Lodge, Pittsburgh

Tchaikovsky's Pathetique – Pittsburgh Symphony Orchestra

The Pittsburgh Symphony Orchestra performs Tchaikovsky's powerful final symphony, the Pathétique, at Heinz Hall.

Friday, May 15 – Sunday, May 17, 2026 · Heinz Hall, Downtown Pittsburgh

Mom's Night Out with the Mama's Den

A special Mom's Night Out concert event at City Winery Pittsburgh featuring the Mama's Den.

Tuesday, May 19, 2026 · City Winery Pittsburgh, Strip District

Family-Friendly

Alice's Adventures in Wonderland – Phipps Summer Flower Show Opening

Phipps Conservatory opens its enchanting summer flower show inspired by Alice's Adventures in Wonderland, featuring immersive botanical displays.

Saturday, May 16, 2026 · Phipps Conservatory, Oakland

Skate the Square at Market Square Rink

Retro roller skating with live DJs, drinks, and themed nights at the Market Square Rink Downtown through May 25 — 75 minutes for $17 with skates included.

Friday, May 15 – Monday, May 25, 2026 · Market Square, Downtown Pittsburgh

Date Night

A Toast to Wonderland – Premiere Party at Phipps

Celebrate the opening night of Phipps' Alice in Wonderland flower show with a ticketed premiere party featuring drinks and the full floral experience.

Friday, May 15, 2026 · Phipps Conservatory, Oakland

Arts & Culture

The Tamburitzans at Pittsburgh Playhouse

A special performance by The Tamburitzans, celebrating Eastern European folk music and dance traditions, at the Pittsburgh Playhouse.

Saturday, May 16, 2026 7:00 PM · Pittsburgh Playhouse, 350 Forbes Avenue, Pittsburgh

A Midsummer Night's Dream – Pittsburgh Ballet Theatre

Pittsburgh Ballet Theatre performs Shakespeare's beloved classic in a full ballet production at the Benedum Center.

Friday, May 15 – Sunday, May 17, 2026 · Benedum Center, Downtown Pittsburgh

Free Events

5th Annual Shadyside Art Festival on Walnut Street

A free outdoor art festival on Walnut Street in Shadyside featuring artists and makers from the region.

Saturday, May 16, 2026 10:00 AM · 5428 Walnut St, Shadyside

Food & Drink

Drag Brunch at Inner Groove Brewing

S&S Productions presents a lively drag brunch at Inner Groove Brewing in Verona, with seating at 11am and showtime at noon.

Sunday, May 17, 2026 11:00 AM · Inner Groove Brewing, 751 E Railroad Ave, Verona, PA

Outdoors & Active

Yinz Run Club at Cinderlands Warehouse

Yinz Run Club hosts a group run at Cinderlands Warehouse in the Strip District with a Skechers shoe demo — test a pair and earn a free drink, run starts at 6:30pm.

Wednesday, May 14, 2026 6:30 PM · Cinderlands Warehouse, Strip District

Sports

Steelers SteelHERS Social at Acrisure Stadium

The Pittsburgh Steelers host a SteelHERS Social event at Acrisure Stadium featuring football activities, photo ops, giveaways, locker room access, and player meet-and-greets.

Thursday, May 28, 2026 5:30 PM · Acrisure Stadium, North Shore