Old Town after dark splits into two worlds: the club corridor with its velvet ropes and bottle sparklers, and a handful of rooms where people actually care about what’s in the glass. Second Story is firmly the second kind — a dim, speakeasy-styled den where the bartenders free-pour conversation and stir drinks like they’re being graded.
The cocktail list rotates, but the play is to name a spirit and a mood and let the rail decide. Food punches above bar-snack grade; this is a full night, not a pre-game stop.
When to go: weeknights are relaxed and conversational. Friday and Saturday it fills by 8:30 PM, and standing room defeats the purpose of the place.