14 Things to Do in Pittsburgh This Week · May 21–24, 2026

Music & Nightlife

Ryan Bingham and The Texas Gentlemen – Still Gettin' Away With It Tour

Texas roots-rock troubadour Ryan Bingham brings his road-worn sound to Stage AE in an indoor show presented by 91.3 WYEP.

Friday, May 22, 2026 7:00 PM · Stage AE, Pittsburgh, PA

The Orbit 4 – Hip-Hop Showcase

A highly anticipated hip-hop showcase returns on May 30 featuring performances by Nsecure, 700myles, Chapo781, Kennetic, and TheRealOuija.

Saturday, May 30, 2026 · Pittsburgh

Outdoors & Active

Yinz Run Club Weekly Run Crew at Mike's Beer Bar

Yinz Run Club's weekly group run starts at 6:30PM from Mike's Beer Bar — all paces and newcomers welcome.

Thursday, May 21, 2026 6:30 PM · Mike's Beer Bar, Pittsburgh

Shore Thing Opening Day

Pittsburgh's beloved riverfront pop-up opens for the season on the North Shore, kicking off summer on the water.

Friday, May 22, 2026 · North Shore, Pittsburgh

Food & Drink

Bites and Pints at Kennywood

Kennywood Park hosts a food and drink festival with bites and craft pints through May 24, making for a one-of-a-kind amusement park culinary experience.

Friday, May 22, 2026 · Kennywood Park, West Mifflin

Arts & Culture

Paul Gertner in Steel City Miracles

Pittsburgh's legendary close-up magician Paul Gertner performs his acclaimed show at Liberty Magic through May 31.

Thursday, May 21, 2026 · Liberty Magic, Pittsburgh Cultural Trust

ASCEND – Immersive Interactive Theater

Pittsburgh Playhouse presents ASCEND, an immersive and interactive theatrical experience running through May 31 — late arrivals not permitted, so come early.

Saturday, May 23, 2026 · Pittsburgh Playhouse at Point Park University, Downtown

Festivals & Special Events

Neighborhood Flea Night Market

An evening flea market and night market pops up at SouthSide Works for a lively Saturday shopping and socializing experience.

Saturday, May 23, 2026 · SouthSide Works, South Side

ROCK THE BOAT – All-White Memorial Day Weekend Party Cruise

An all-white-attire party cruise on the EMPRESS celebrates Memorial Day Weekend with dancing, music, and river views — nearly sold out.

Saturday, May 23, 2026 10:00 PM · EMPRESS, Pittsburgh

Date Night

Lyle Lovett Up Close: Songs & Stories

Legendary Americana artist Lyle Lovett performs an intimate multi-night run at City Winery Pittsburgh, pairing live music with dinner service.

Wednesday, May 27, 2026 · City Winery Pittsburgh, Strip District

Free Events

Lawrenceville Farmers Market Season Opening at Bay 41

The Lawrenceville Farmers Market kicks off its 2026 season at Bay 41, offering fresh produce, local goods, and community connection in the heart of Lawrenceville.

Friday, May 22, 2026 · Bay 41, Lawrenceville

Art on Braddock at Frick Park

The City of Pittsburgh's newest market 'Art on Braddock' features local creators, food and beverage vendors, and community programming in the Regent Square neighborhood.

Saturday, May 23, 2026 · Braddock Avenue at Frick Park, Regent Square

Open Up Pittsburgh May Dance Party

Open Up Pittsburgh's inclusive community dance party returns on May 29 — open to all abilities and backgrounds.

Friday, May 29, 2026 · Pittsburgh

Family-Friendly

RANDYLAND Living Art Museum Tour

A guided tour of Pittsburgh's beloved colorful folk-art landmark Randyland — a joyful, community-spirited experience for all ages.

Sunday, May 24, 2026 2:00 PM · Randyland, Pittsburgh