Spooky Season in the Ghoulden Triangle: Your Guide to Thrills & Chills in Downtown Pittsburgh

Spooky season is upon us, and Downtown Pittsburgh is packed with frightfully fun events to enjoy! From sipping themed cocktails to catching a surprise horror movie screening, there’s no shortage of ways to get into the Halloween spirit. Whether you’re in the mood for eerie adventures or cozy fall fun, Downtown is the place to be this month — and we’ve rounded up some of the best events to make the most of it. 🎃🍂

Haunted River Cruises

📍Gateway Clipper Fleet

📅 Friday, September 26 – Thursday, October 30

Set sail for Halloween fun with the Gateway Clipper Fleet! The Haunted Three Rivers Cruise runs through the end of October, featuring eerie tales and spooky Pittsburgh lore. For a lighter take, enjoy the Boo ’n Brew Dance Cruise on October 25 or 105.9 The X’s Halloween Cruise on October 30. Families can also hop aboard the Halloween Fun Cruise on October 25 for trick-or-treating, a DJ dance party, prizes, and more!

Cocktails from the Crypt Pop-Up Bar

📍130 7th St

📅 Friday, October 10 – Saturday, November 1

Cocktails from the Crypt is back from the dead for another hauntingly fun Halloween season! This chilling pop-up bar blends eerie ambiance with expertly crafted cocktails, turning every corner into a perfectly spooky photo op. Gather your friends for a night out filled with ghoulish drinks, haunting decor, and plenty of surprises lurking in the shadows. Whether you’re a horror buff or just love a good themed cocktail, this crypt is calling your name.

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Haunted Speakeasy at the Omni William Penn

📍Omni William Penn

📅 October 2 – November 1

Something wickedly fun is brewing in downtown Pittsburgh, at an original Speakeasy. Step into a haunted hideaway where potions are poured, cobwebs are chic, and every cocktail comes with a curse (the fun kind). Whether you’re in it for the boos or just creeping it real with friends, this Halloween pop-up is your go-to for ghoulish vibes, eerie elixirs, and frightfully good photo ops. Costumes optional—but highly encouraged.

Steel City Spooky Markets

📍Frankie Pace Park

📅 Saturday October 18 & Saturday October 25

The Steel City Spooky Market is in full swing, bringing eerie delights to Downtown every Saturday through the end of October! Explore a market filled with strange and unusual finds — from eerie art and tarot cards to crystals, taxidermy, and more. With rotating vendors each week, there’s always something new to discover and plenty of spooky charm to get you into the Halloween spirit.

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Fall Fest at the Pittsburgh Playhouse

📍Pittsburgh Playhouse

📅 Thursday, October 16 – Sunday, October 26

After its major success last year, the Pittsburgh Playhouse Fall Fest returns for another season of fun! This year’s celebration will take place inside the Pittsburgh Playhouse and extend onto Forbes Avenue, featuring food and drinks, games, local vendors, arts and crafts, and a special Halloween performance of Boo’s Halloween House Party.

Pittsburgh Pop Up: Boozy 5k

📍North Shore Riverfront Park

📅 Friday, October 17

Run straight into the Halloween spirit at the Boo-zy 5K! Both runners and walkers are welcome, with walkers starting at 7 p.m. and runners at 7:30 p.m. Participants can enjoy an alcoholic beverage at each of the three drink stops along the route, with non-alcoholic options available too. After crossing the finish line, celebrate with food, music, and prizes for the best costumes.

Día de los Muertos Kick-Off Lunch

📍Kara Family Lobby at the Greer Cabaret Theater

📅 Thursday, October 23

Kick off the Día de los Muertos celebration at the Greer Cabaret Theater with a flavor-packed lunch! Enjoy authentic tacos, tamales, and more as you celebrate the season with delicious food and lively entertainment. Then, take part in a hands-on sugar skull painting activity that honors the vibrant beauty and spirit of this cherished holiday.

Haunted History Center Halloween

📍Heinz History Center

📅 Sunday, October 26, 2025

If you’re looking for a day of family-friendly Halloween fun, the Heinz History Center is the place to be! Kids 17 and under receive free admission and can enjoy eerie tales, spooky crafts, festive treats, and themed drinks from The Coffin Bean & Co.

Steel City Horror Show

📍Harris Theater

📅 Sunday, October 26

The Steel City Horror Show returns to the Harris Theater just in time for the spookiest month of the year! October is all about thrills and chills, and this month’s mystery movie is sure to deliver both. Last month’s audience was teased with one cryptic clue — “DREAM.” What could it mean? There’s only one way to find out, grab your popcorn and prepare for a fright-filled night in the Steel City.

Haunted Fest Pittsburgh feat. Levity and Daily Bread

📍Stage AE

📅 Friday, October 31

If you’re looking to end spooky season on a high note, Haunted Fest Pittsburgh is the place to be. Taking over Stage AE Outdoor on October 31, the festival features performances from Levity, Daily Bread, and Capochino. Whether you’re there for the music or the atmosphere, Haunted Fest brings all the energy you’d want from a Halloween night out.

Dracula

📍Benedum Center

📅 Friday, October 31 – Sunday, November 2

If jump scares aren’t your thing, enjoy a more refined Halloween experience as Count Dracula returns to the Benedum Center. Michael Pink’s Dracula transforms Bram Stoker’s classic into a breathtaking ballet filled with romance, suspense, and stunning visuals. With dramatic choreography, opulent costumes, and a haunting score, this gothic performance offers a perfectly chilling night at the theater.

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