As the crisp autumn air FINALLY settles over Pittsburgh (those 80+ degree days felt like they would never end), the city comes alive with events for all ages from October 27 to November 2. Whether you choose to take in the last of the Halloween scares with various parties or wish to take advantage of some simple downtime, we promise there’s something that’s worth leaving the house for. After all, once November 2 hits, we’ll officially be switching over to holiday mode!
Pittsburgh Events Happening October 27-November 2
Hallo-week Paint + Sip & Costume Contest
October 29, Urban Tap
Get ready to sip, paint, and compete in the Hallo-week Costume Contest! This spooky-chic night at The Urban Tap in Shadyside combines creative fun, cozy vibes, and festive flair. Your ticket includes two specialty cocktails (mocktails and espresso bar options available), a small paint-by-numbers canvas, a spooky charcuterie cup, exclusive treats, and automatic entry into the costume contest. Enjoy local vendors, a trick-or-treat bar, and drinks all night.
Woodworking 101 with David Bielewicz
October 30, Contemporary Craft
Learn the fundamentals of woodworking in this beginner-friendly workshop. Students will explore core woodshop machines, safety procedures, and the lumber milling process—turning rough-sawn boards into dimensional lumber. Participants will gain confidence using the studio space and tools, and will create sample pieces demonstrating their new skills. This course is an excellent introduction before taking other project-based workshops.
Bugs Bunny at the Symphony with the Pittsburgh Symphony Orchestra
October 31-November 2, Heinz Hall
Celebrate Halloween at Heinz Hall with costumes, candy, and the return of Bugs Bunny at the Symphony! The Pittsburgh Symphony Orchestra brings classic Looney Tunes to life with live music perfectly synced to beloved cartoons on the big screen. Festivities kick off Friday with special Halloween fun before the show, making this the perfect outing for families and friends alike.
Phantom’s Pour: A Halloween Masquerade
October 31, Black Dog Wine Company
Step into an evening of decadence, disguise, and dark delight at Black Dog Winery’s Halloween masquerade. Enjoy live music from Cover 2-Acoustic Show for their Black Dog debut, costume contests, and hauntingly crafted cocktails in a setting made for mystery. Each ticket includes a complimentary glass of wine and sharable snacks.
Hops & Hex at Trace Brewing
November 1, Tace Brewing
Celebrate spooky season at Hops & Hex, a night of haunted fun for the adults hosted by The Pittsburgh Creative. Guests can shop local vendors, get a tiny tattoo, enjoy close-up magic, and even enter to win the costume contest. With eerie local lore woven into the evening, this witchy gathering offers a playful mix of shopping, entertainment, and Halloween vibes all while sipping on your favorites at Trace Brewing.
Story by Kylie Thomas
Featured Photo Courtesy of Trace Brewing
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