Thursday, Sept. 14-Sunday, Sept. 17: Pittsburgh International Jazz Festival at Highmark Stadium & August Wilson African American Cultural Center
Jazz fans get ready: The 13th annual edition of the locally produced festival kicks off with the Uhuru Jazz Session featuring Nigel Hall and Madison McFerrin. Don’t miss Friday’s intimate Taste of Jazz party — fusing jazz stylings with delights from Pittsburgh’s hottest restaurants. Ledisi, Hubb’s Groove, Kevin Howard, Jonathan Barber and DJ Selecta are sure to bring the heat. Weekend highlights showcase powerhouse sets by legendary veterans and rising stars alike, including Jimmy Jamm & Terry Lewis, Bob James, Howie Alexander, Spanish Harlem Orchestra, Orrin Evans, Mumu Fresh and Gregory Porter. Schedule and tickets.
Thursday, Sept. 14: Sanctuary Art + Honors Opening Reception at Hot Metal Bridge Faith Community
Art and music converge on the South Side to celebrate safe spaces and honor the creative contributions of the local LGBTQIA+ community. Organizers write that the project serves as a “direct contrast to the more than 520 anti-LGBTQIA+ bills that have been introduced in state legislatures across the country this year alone.” Along with 10 featured visual artists, the free presentation includes local musicians on most nights of the exhibit, which runs through Sept. 22. Tonight’s opening reception is a ticketed event featuring comedian Amanda Averell, co-owner of the Burning Bridges Comedy Club, plus music by Brad Yoder. Schedule.
Friday, Sept. 15-Sunday, Sept. 17: Oktoberfest at Penn Brewery
Pittsburgh’s oldest and largest brewery is the perfect place to ring in beer month — and pre-game fall fun. Head to the North Side for this beloved tradition spanning two weekends. Pair award-winning German-style craft beers with Bavarian staples like wurst, potato salad, pretzels, pierogies and strudel. Plenty of outdoor patio seating and live music will keep things festive.
Friday, Sept. 15: Pittsburgh Fashion Week at The Wintergarden at PPG
It’s a new era for Pittsburgh Fashion Week, which debuts a new owner, producer and manager — with Diamonds by Rothschild CEO Henry Rothschild at the helm. Downtown’s iconic Wintergarden at PPG provides a glistening backdrop to the runway show spotlighting talented designers who are dedicated to “fashion, education, diversity, inclusion, mentorship and sustainability.” Participating artists, who each will unveil a collection of six looks, are Emily Rouse, Deijia Williams, Starr Thomas, Brian David Thompson, Suz Pisano, Bradford Mumpower, Michael Kouri and Malcolm Staples. Tickets.
Saturday, Sept. 16: FlyBy 5K at Pittsburgh International Airport
Why run around a track when you can run along a runway? This running (or walking!) experience lets participants onto the airfield and taxiways. It’s fun and easy for anyone to earn their wings at this family-friendly race, with a 5K course, a 2-mile fun run/walk and event festivities. Proceeds benefit the Allegheny County Airport Authority Charitable Foundation. Register now to take flight.
Saturday, Sept. 16: Community Mutt Strut on the North Shore
11 a.m.-2 p.m.
Strut your stuff to help veterans, first responders and civilians in need. Guardian Angels responds to the difficult reality that approximately 22 veterans take their lives daily. But when paired with a service dog, the suicide rate among recipients drops to zero. Held during Suicide Prevention Month, the canine celebration includes a dog costume contest, prizes, food, pet and veteran vendors, music, and a silent auction. Debuting its new location along the North Shore, the FUNdraising event helps train service dogs. Register.
Saturday, Sept. 16: Rocktoberfest at SouthSide Works
Pittsburgh’s newest brew fest returns to put a musical spin on the signature Oktoberfest festivities. It’s that quintessential time to embrace crisp weather, layered clothing (lederhosen optional!), outdoor socializing, live music … and beer. The Town Square will be hopping with craft brews, cocktails and seltzer, yummy bites and dancing. See how Zero Fossil’s solar stage uses sunshine to power live music with local acts bringing the fall soundtrack. Featured breweries are Old Thunder, Fermata, Levity and Inner Groove. Schedule.
Saturday, Sept. 16: Arbor Aid at Tree Pittsburgh
The transition from summer to fall is an idyllic time to party under the stars to support Mother Nature. Celebrate the benefits of the urban forest at Tree Pittsburgh’s beautiful campus along the Allegheny River. The benefit bash serves up local delicacies including pierogies and even a themed cookie table. Toast the trees with brews from Penn Brewery and ciders from A Few Bad Apples and enjoy live music by Chet Vincent and Mani Bahia & the Mob. Tickets.
Saturday, Sept. 16: Three Stooges Film Festival at the Harris Theater
Calling all Moe, Larry, Curly — and Shemp — devotees to the Cultural District! Join plumbers, salesmen, detectives, antenna installers, Census takers and even exterminators to LOL for an entire night dedicated to the iconic American comedy team. Along with six of the best “Three Stooges” shorts spanning 1937-1952, there will be trivia, prizes and audience polls. Bonus laughs: Kids 12 and under are free! Tickets.
Sunday, Sept. 17: Pittsburgh County Fair at Allegheny Commons Park
10 a.m.-5 p.m.
It might be in the city but the inaugural Pittsburgh County Fair has all the ingredients for a fantastic late summer day. An urban agricultural celebration of all things handmade and homegrown, the fair is produced by Ferment Pittsburgh and Grow Pittsburgh. Channel your inner farmer, forager and fermenter, meet local growers and makers, enter the Best Tomato in Pittsburgh Contest and more. Schedule.