8. GAP Relay: Oct. 15 & 16
Experience the great outdoors along the Great Allegheny Passage when this fall favorite returns to challenge and inspire runners. Unveiling a new course for the 150-mile relay — as well as a new 60-mile, one-day option — the GAP Relay is open to runners of all fitness levels. There’s more good news: Runners will now start the carbon-neutral event right here in Pittsburgh rather than in Cumberland, Maryland. Teams of eight, six or four will tackle the full 150-mile distance. If you want to see what all the excitement is about, join a smaller team of two or four runners to experience the 60-mile Saturday course. There’s even a finishers’ party like no other. Register now.
9. Steel City Big Pour at Construction Junction: Oct. 16
Beer and conservation will converge when this granddaddy of brew fests returns for frothy in-person fun. Grab tickets now because the event has been reconfigured to offer one evening session only from 5 to 8 p.m. Within CJ’s cool warehouse environs, you’ll sample suds crafted by 14-plus local and national breweries — from Allegheny City, Arboretum Trail and Dancing Gnome, East End and Toppling Goliath. The brewhaha will also feature live music and art and a maker market. Tickets include a Big Pour T-shirt, taster glass and brew caddy — plus scrumptious food from local restaurants. Proceeds support the reuse and conservation of building materials. Buy tickets.
10. Monster Pumpkins Festival at 3 Crossings: Oct. 16 & 17
Where can you watch world-renowned carvers turn pumpkins into a medieval tableau? Or see graffiti artists spray paint towering walls of pumpkins? How about competing in a pumpkin pie plunge? Monster Trucks have nothing on these colossal cucurbits. Back with a sprawling new home in the Strip, the city’s favorite new pumpkin patch will create a sea of orange along Railroad Street. Squash lovers can take a horse-drawn carriage ride, watch glass pumpkins being made, check out a 2,500-pound Atlantic Giant pumpkin and much more. The fall fantasia will feature artisan vendors, seasonal foods and Halloween-themed attractions. The grand gourd finale will be when a 1,800-pound pumpkin is dropped 100 feet into a pool of water. Why?! All to raise money for Project Bundle Up.
11. John Waters at Carnegie Music Hall: Oct. 21
Be there when John Waters makes his first in-person appearance since the start of the pandemic. Whether you adore him for his seminal cult films such as “Polyester” and “Hairspray,” his devious wit, his signature pencil stashe, or his “Charm City” upbringing, you can’t miss the inimitable writer and director when he graces Pittsburgh fans with a brand-new version of his solo stand-up show. The revamped take on his nationally touring monologue will celebrate the iconic personae, illustrious career and “obsessional tastes” that can only be attributed to Waters. Named an officer of the Order of Arts and Letters in France in 2018 and nominated for a Grammy Award for Best Spoken Word Album, Water’s latest book, “Mr. Know-It-All: The Tarnished Wisdom of a Filth Elder,” was published in 2019. Buy tickets.
12. Classic Horror at Carrie Carpool Cinema: Oct. 29 & 30
Celebrate Halloween in the long tall shadows of a steelmaking relic. Be spooked by a double feature weekend of classic horror films as the wind howls in the distance, the moon rises in the night sky and the leaves crunch underfoot. The weekend kicks off with The Bride of Frankenstein, James Whale’s 1935 classic starring Boris Karloff. For even more chills, head back on Saturday — if you dare — to catch John Carpenter’s 1982 horror flick, The Thing, starring Kurt Russell as a researcher in Antarctica who encounters a parasitic extraterrestrial life form. Stay late into the witching hour for a ghost tour of the landmark site. Buy tickets.
For live music, check out 20 must-see live music events this September in Pittsburgh.