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The Saturday before Halloween is the main event: biggest parties, biggest crowds, and the night costumes are mandatory. Halloween night itself skews mellower with locals and die-hards, often with cheaper covers. Big years give you both weekends, so split them, marquee party on peak Saturday, favorite neighborhood bar on the night itself. Fridays split the difference on price and crowd.
Arrive before 10 pm at clubs and big parties; lines go from ten minutes to an hour between 10 and 11 on peak Saturday. Have IDs out and masks off as you approach, and know that "ticketed" rarely means "walk straight in" at capacity. If the line looks hopeless, pivot to your second venue early rather than sunk-costing 45 minutes on the sidewalk.
The basics, executed: drinks stay watched or covered and never accepted open from strangers, the group uses a buddy check-in at each venue change, and live locations stay shared until everyone's home. Masks hide faces, so confirm identity before leaving with anyone. Preset the ride plan, keep your phone charged with a battery backup, and screenshot tickets and addresses against dead signal.