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Downtown Events & Happenings to Get in the Halloween Spirit

Monday, October 18, 2021

Halloween is just around the corner, and we have the ultimate guide to get into the spirit of all things fall. From costume parties on the three rivers to finding fresh fall produce around Downtown, there are so many things to do this season.

Looking for fall-themed treats around the city? Explore our guide on Where to Find Pumpkin Spice (and More Fall Treats) Downtown.

Market Square Farmers Market

Thursday, October 28 from 10 a.m. – 2 p.m. | Free to Attend
See your favorite vendors dressed in costume and visit their booths for tasty treats. Enjoy a special Halloween set live from Slim The DJ on the PNC Stage from 11:30 a.m. – 1:30 p.m.

Mellon Square Block Party

Thursday, October 28 from 5 – 8 p.m. | Free to Attend
Come out for the final Mellon Square Block Party of the season, hosted by the Pittsburgh Parks Conservancy! Enjoy live music, games, scary outdoor movies, and cocktails and food provided by Talia.

Hocus Pocus Movie Night with the Sanderson Sisters at the Hard Rock Cafe

Thursday, October 28 from 7 – 9:30 p.m. | $10 Tickets
Calling all witches! Meet up at the Hard Rock Cafe for a special Halloween event featuring a screening of the Walt Disney Pictures Halloween favorite, HOCUS POCUS. This all-ages event will feature a screening of the movie, special Hocus Pocus trivia, prizes, and will be hosted by Pittsburgh’s own Sanderson Sisters.

Pittsburgh Tattoo Company

Friday, October 29 (Must be 18+)
Get a spooky tattoo for a scary-good price at Pittsburgh Tattoo Company! Choose from pumpkins and ghosts, or whatever you love most to get in the spirit of Halloween.

Halloween Party at Howl at the Moon

Friday, October 29 from 6 p.m. – 2 a.m.
Get your costumes ready for Halloween! Come have a ghoulish time at the annual Howl at the Moon Halloween Party with drink specials, games and – everyone’s favorite – a costume contest with $500 in prizes! Don’t forget to enter to win a Happy Hour party by entering your information in the form here.

Five Iron Halloween Party

Friday, October 29 from 8 – 11 p.m. | Tickets starting at $20
Come for the golf and stay for the boos! Five Iron Golf and Espolón Tequila are teaming up to host a spooktacular Halloween event full of boos, brews and birdies. Treat yourself to drink and open bar packages with Espolón tequila, a costume contest, longest drive competition, giveaways and more.

Halloween Party at Redbeard’s on Sixth

Friday, October 29 from 10 p.m. – 2 a.m.
You’re invited to a Halloween costume party at Redbeard’s! Dress your best and participate in the costume contest, dance to music from DJ Billy Badazz, and enjoy adult tricks and treats.

Terror at Tetto

Saturday, October 30 from 2 p.m. – 2 a.m.
Come dressed in your best Halloween costume and enjoy specialty Halloween cocktails, food specials, costume contests with prizes, and more at Sienna Mercato’s rooftop bar!

Saturday Night Market

Saturday, October 30 from 5 – 7 p.m. | Free to Attend
Go trick-or-treating right in Market Square! Pittsburgh’s most creative vendors are celebrating Halloween in costume with decorated booths and treats and sweets. Shop spooky art pieces from After Dark Illustrations, knit items that are perfect for fall from Jekyll and Plaid, and even Halloween-themed clay earrings from Peace Love n Little Gems. Visit Songbird Artistry’s decorated booth to get in the spirit of Halloween. Hear Miss Freddye and The Yeggs perform scary-good music and enjoy circus tricks from O’ryan the O’mazing.

Pittsburgh City Paper Downtown Halloween Cocktail Crawl

Saturday, October 30 | No Ticket Necessary (Must be 21+)
Visit the Pittsburgh City Paper and Bacardi booth at the Saturday Night Market to pick up a guide to the Downtown Halloween Cocktail Crawl. Play games, spin the prize wheel, and take spooky pictures in front of their backdrop! Explore spooky cocktails from 15 bars and restaurants around Downtown including the Apple Chai Margarita from August Henry’s Burger Bar, the Pumpkin White Russian from Emerson’s, and the Half Blood Prince from täkō.

Monster’s Ball at Revel & Roost

Saturday, October 30 from 9 p.m. – 2 a.m. | Variety of Ticket Packages Available (Must be 21+)
See Revel + Roost transform into a Monster’s Ball Halloween Costume Party! Win up to $500 cash by dressing up in your scariest, sexiest, or funniest Halloween costume, and vibe to the best music all night long. Admission is free before 10 p.m. with RSVP, and food is complimentary until midnight.

Penn Society Halloween Party

Saturday, October 30 at 10 p.m. | Reservations Recommended – Please email kellyg@ampdgroup.com
Make Penn Society your first stop on the Downtown Halloween Cocktail Crawl! Indulge in their Magic Trick cocktail that features a magical combination of Grey Goose, blackberries, St. Germaine, lemon, and citrus smoke. Also, join Penn Society for their annual Halloween party and for the chance to win a $250 gift card for the best costume. Music will be provided by DJ Hipnotik.

Liberty Magic: Todd Robbins’ HAUNTED DECEPTIONS

Saturday, October 30 through Sunday, October 31 | $45 Tickets
Is death the end of existence? And if not, is it possible to make contact with the dead? Todd Robbins invites you to join him as he reaches out to the dead with his new immersive seance experience, Haunted Deceptions. Mr. Robbins will use arcane retro-paranormal ghost hunting techniques to open the souls of the living in order to invite the dead to return.

Propel Schools Foundation – Trick or Trot 5K & Fun Run

Sunday, October 31 at 9 a.m. | Registration ends October 24
Put on your best costume and head to the North Shore Riverfront Park to run or walk along the Monongahela River in support of the Propel Partners in Wellness Program. Stay after the races to grab a snack from some local food trucks and dance to the DJ while you visit booth sponsors for fun, games, and wellness education!

Black & Ghost Tour

Adults $25, Children $15 (age 6-13)
Experience the spookiest of Pittsburgh’s Downtown! Get to see outstanding historic landmarks during the quiet evening hours and learn about their history and which spirits lurk in them…

Cocktails From The Crypt

Open Daily from 4 p.m. – 12 a.m. until Halloween (Must be 21+)
Come in if you dare… to Cocktails From The Crypt, a Halloween cocktail pop-up bar! Sip on scary-good creative cocktails like Transfusion, Crypt Keeper, and Bordello of Blood for a spooky night out.

Whiskey Walking Tour

Saturdays | Adults $25 (Must be 21+), children and dogs welcome with advance notice and proper supervision
Warm up on brisk fall days with a Whiskey Walking Tour. From the mill to the still, whiskey has been a cornerstone in Pittsburgh’s history. Discover how whiskey has fueled political, labor and social movements throughout the region and find hidden speakeasies around the Burgh. The tour includes a sample of the oldest and longest continuously produced whiskey in America (or a hot toddy for the colder days), 3 additional samples of whiskey, as well as discounted whiskey cocktails for only $5 from Wigle Whiskey.

Liberty Magic: Chris Capehart in “Journey of the Master”

Tickets starting at $40
Fall for mind blowing, close-up illusions created by accomplished magician Chris Capehart and join him on the Journey of the Master.

Haunted Pittsburgh Downtown Walking Tour

Thursdays – Sundays | Adults $18, Children $10
Haunted Pittsburgh is the curator of Pittsburgh’s nightmares and of all things that go bump in the night. The Downtown tour starts at the City-County Building. See the many haunted sites around the city and hear their greatest ghost stories.

The Gateway Clipper

The Gateway Clipper has a variety of Halloween-themed cruises to fit every vibe!

Thriller Halloween Moonlight Dance Cruise
Friday, October 29 from 11 p.m. – 1:30 a.m. | Tickets starting at $35 (Must be 21+)
Sail the Three Rivers aboard Pittsburgh’s only floating dance club with a full service bar! Jam out on the water with WAMO 1073 and enter the Halloween Costume Contest for a chance to win great prizes.

A “Spooky” Afternoon of Halloween Fun
Saturday, October 30 from 1:30 – 3:30 p.m. | Adults $32, Children $20
Come aboard a Pittsburgh sightseeing tour for a kids’ costume party with frightfully friendly characters, tons of fun prizes and more! Enjoy a “spooky” afternoon of Halloween fun with music, dancing and treat bags for all the kids.

Boo N Brew Halloween Dance Cruise
Saturday, October 30 from 8 – 11 p.m. | Tickets starting at $30 (Must be 21+)
Experience free psychic and tarot card readings, prizes and mingle with your favorite BOB FM on air personalities out on the docks at 6 p.m. At 8 pm, the party hits the water with the band “Random Play” playing all your favorites hits – BOB FM style. Don’t forget to wear your Halloween costumes for your chance to win great prizes including concert and event tickets, and a grand prize – $1500 Green Apple Barter Travel Certificate!

Haunted Pittsburgh Cruise
Fridays, Saturdays, & Sundays | Adults $32, Children $20
Does the “Monongahela Monster” really exist? Who haunts the old Allegheny County Jail? Learn the answers to these questions and hear a rich collection of ghost stories and tales aboard this spooky cruise!

The Dinner Detective Murder Mystery Dinner

Book now through December 18 | Tickets starting at $65.99
Tackle a challenging crime while you feast on a fantastic dinner. Just beware, the criminal is lurking somewhere in the room, and you may find yourself as a Prime Suspect before you know it! (Hurry, tickets sell out fast!)

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