Southold

Southold sits on Long Island's North Fork, the quieter, wine-focused counterpart to the Hamptons across the bay - and BarFinder's data reflects that directly: wineries make up 17 of the town's 23 listed venues. Real local wineries like Duck Walk Vineyards, Old Field Vineyard, and Kontokosta Winery anchor the North Fork wine trail, with only a handful of classic bars and a brewery rounding things out. A night out here means a vineyard tasting room far more often than a traditional bar.