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Read the listing: "costumes encouraged" means half the room dresses up and nobody cares, while "costume required" events can refuse the door or charge extra without one, especially themed balls. Peak Saturday, you'll feel more out of place without a costume than in one. The minimum viable move: one strong accessory, hat, cape, face paint, that reads as participation.
Often the best value of the season: trivia nights, themed dinners, scary-movie bar screenings, and early crawls run cheaper, quieter, and more conversational than peak Saturday. Weeknights suit costumes you actually want people to look at, and bartenders have time to make the themed cocktails properly. Save the marquee spend for the big Saturday and fill October's calendar with weekday gems.
Older bars are the wildcard, basement venues, narrow doors, step-up entries, so call or message the venue about step-free entry and accessible restrooms before buying tickets, and ask where the accessible entrance actually is, since it's often around back. Crowded costume nights complicate navigation, so early arrival helps. Ticketed seated events, themed dinners, cabarets, are generally the more reliable choice.