10 Wickedly Fun Things To Do in Downtown Pittsburgh This Spooky Season

As Halloween approaches, there’s no shortage of spooky sights and fun frights in Downtown. Whether you’re looking for a pop-up bar for your next night out or a family-friendly haunted river cruise, there is something for everyone to enjoy. They don’t call us the “Ghoul”-den Triangle for nothing! 👻

Haunted River Cruises

📍Gateway Clipper Fleet Docks
⏰October 1st – October 26th

Besides their classic Haunted Three Rivers Cruise, the Gateway Clipper offers special tours throughout the season for a truly terrifying time. Secure your spot on the Thriller Halloween Moonlight Dance Cruise or the Boo N Brew Halloween Dance Cruise for a spooky evening on the water. Or enjoy a treat for the whole family with the Halloween Fun Kids Cruise on Saturday, October 26th! 

Cocktails from the Crypt

📍130 7th St
⏰October 10th – November 3rd

The long-awaited opening of Cocktails from the Crypt is finally here! This fan-favorite Halloween pop-up bar has returned, and they’re serving everything from the classic Vampire Ballerina cocktail to their new Crypt Spritz. This pop-up is open Wednesday through Sunday from 5 p.m. to midnight. Grab your friends and stop by for some bubbling brews! 

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Halloween: Season of the Sketch

📍Arcade Comedy Theater
⏰October 17th & 18th

This two-night Halloween special from Arcade Comedy Theater will get you into the spooky season spirit. From the masterminds behind “Revue This!” and “Sketch Madness” comes this chillingly hilarious sketch show. Grab your friends and head out for a night of ghoulish giggles!

Fall Fest at Pittsburgh Playhouse

📍Pittsburgh Playhouse
⏰October 17th – October 27th

The first Pittsburgh Playhouse Fall Fest is officially here! Enjoy two wicked weekends of fun featuring live entertainment, carnival boots, local vendors, tarot readings, and plenty of food and drinks. Attend performances of the Playhouse’s brand-new Halloween show, Boo’s Halloween House Party. This Fall Fest brings frightening fun for the whole family.

Hocus Pocus Bar at Barcadia

📍24 Market Square
⏰October 22nd – October 31st

A spooky spin is coming to Barcadia this season. For ten days only, a Hocus Pocus Halloween Bar will be taking over! Head to the upper floor of Barcadia for some sinister sips. Check out the schedule of events for the week, which includes everything from karaoke night to a costume party! The drinks are truly to die for.

Fright Up Nights at the Night Market

📍Market Square
⏰October 25th & 26th

The final weekend of Market Square’s Night Market will be the most thrilling of the season. For two nights, Market Square will be transformed into a haunted Halloween marketplace. With themed entertainment, spooky decor, and special vendors, there is something for the whole family to enjoy. No tricks, just treats at Fright Night!

Ofrenda Happy Hour 

📍The Lounge at the Greer Cabaret Theater
⏰October 24th from 6 p.m. to 9 p.m.

In collaboration with the Pittsburgh Metropolitan Area Hispanic Chamber of Commerce (PMAHACC), join the Pittsburgh Cultural Trust for a lively happy hour event to kick off the celebration of Día de Los Muertos! Enjoy a taco bar and sip on signature cocktails inspired by Mexican and Latin flavors while enjoying a vibrant atmosphere with DJ Mateo Mattos spinning tunes to keep the energy high! 

Howl at the Moon Halloween Party: Night of the Undead

📍125 7th Street
⏰October 25th from 6 p.m. to 2 a.m.

Howl at the Moon will host an unforgettable night of the undead. Their Halloween Party will feature spooky drinks like the Voodoo Ranger IPAs and Sweet but Psycho Cocktails and Buckets. Take home a win with their iconic costume contest. Secure your spot now for a ghoulishly good time!

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Ritual House Halloween 

📍524 William Penn Pl
⏰October 26th from 8 p.m. to 1 a.m.

This local favorite is cooking up a spooktacular Saturday night! Join Ritual House on Saturday, October 26th for their Halloween celebration. Starting at 8 p.m., enjoy a night of creepily crafted Halloween cocktails and live entertainment from a DJ. Make sure you come in your best costume!

Día de los Muertos Lunch Event

📍The Backyard at 8th & Penn
⏰October 30th from 12 p.m. to 1:30 p.m.

Head to The Backyard for a vibrant celebration of Mexican cuisine to celebrate Día de los Muertos! Savor authentic tacos, tamales, and more as you immerse yourself in the lively atmosphere, complete with a performance by Mariachi Internacional!