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October is the swing month: afternoon events can be warm while anything after sunset drops fast, so the answer is always layers, base, zip layer, packable shell, plus closed shoes for grass and gravel venues. Toss gloves and a beanie in the bag after mid-October for night tours and outdoor screenings. Check the hourly forecast at event time, not the daily high.
Stake out the route, not the staging area: arrive 30-45 minutes early at a mid-route spot with a wall or storefront at your back for kids' sightlines. Bring your own lantern or glow items only if the event invites it. Transit beats driving, since road closures wrap the route, and know the dispersal point so your group reunites after the crowd releases.
Community events run on volunteers, and signing up transforms the season: host a trunk at a trunk-or-treat, judge a costume contest, staff a festival craft table, or join a parade group. Sign-ups post in September through schools, libraries, and neighborhood groups, and shifts are usually two or three hours, leaving time to enjoy the event. Volunteering is also the best free ticket in town.