City Winery sits on Beverly Street between Haymarket and North Station, a short walk from Faneuil Hall — equal parts working urban winery, restaurant, and music hall. While the main stage draws national touring names, the Haymarket Lounge is the intimate side room, where singer-songwriters and small Boston ensembles play close enough to touch while the house pours wines made on the premises.

Expect table seating, a dinner menu of elevated comfort food, and a wine list built around the house’s own small-batch bottlings. The lounge suits date nights and low-key evenings more than rowdy ones — you’re there to listen, sip, and linger. Check the calendar for the lounge’s rotating lineup alongside the venue’s comedy and wine events.