September 30 & October 1
Various times

It’s home to world-class universities and hospitals (aka eds & meds), is Pennsylvania’s third biggest economic corridor and brims with culture. And thanks to its towering Gothic landmark (the tallest educational building in the Western hemisphere), it can be spotted for miles all around the city.

Oakland Forever
Courtesy Oakland Forever.

The best place to explore Oakland—where some 100,000 people work, study, live and play—is at this weekend’s annual showcase of the neighborhood. One big celebration of the people, places and things that make it fantastic, the free all-ages festival is your chance to find out why Oakland has been dubbed “the world in a neighborhood.”

Oakland’s premier two-day community fest, which takes place this year in conjunction with the 200th anniversary of Pittsburgh’s incorporation, spans the bustling central business district to show off a rich historical legacy, 21st-century innovation hubs, and strong community pride. Festival-goers are invited to explore countless area amenities—from arts and culture and higher learning, to parks, restaurants, boutiques, and more.

Oakland Forever kicks off Friday with a festive Night Market and Fashion Show from 5 to 11 p.m. along S. Bouquet Street. Local vendors will sell an array of handmade merchandise such as clothing, jewelry, art, gifts and prepared foods.

Over at Oakland’s new Forbes Digital Plaza, the fest will host live music by Good Dude Lojack, Indigo Zoo, Slowdanger and others. Don’t miss Friday night’s Fashion Show—also in the Digital Plaza—organized by style consultant and Art Institute of Pittsburgh profosser Suzanne Mauro, which will feature work by six local designers.

From 2 to 10 p.m. on Saturday, attendees can enjoy an urban playground featuring brand new sports, street games, social activities and outdoor recreation during City of Play’s free Come Out & Play Festival.

The Brass Roots
The Brass Roots

Also on Saturday is the outdoor movie night on the sprawling Schenley Plaza lawn. Spread out a blanket, grab some popcorn and watch two cinema classics—the 1999 action-comedy, Inspector Gadget, starring Matthew Broderick, and the 2004 sports docudrama about the U.S. men’s hockey team, Miracle, featuring Kurt Russell.

Saturday’s events in Schenley Plaza will also feature live music by Pittsburgh-based ensemble, The Brass Roots.

Looking for more events? Read our 12 Pittsburgh events not to miss in SeptemberEverything you need to know about Pittsburgh concerts in September and 10 great family adventures in Pittsburgh this September feature stories.

Jennifer has worked at the Mattress Factory, Brooklyn Museum of Art and Dahesh Museum of Art and is co-author of Pittsburgh Signs Project: 250 Signs of Western Pennsylvania. She also is co-coordinator of Handmade Arcade. Musically, she is in a band called The Garment District and is a founding member of Brooklyn's The Ladybug Transistor.