Henry's on the Market has been at 54 North Market Street since 1932, which makes it the oldest continuously operating restaurant in Charleston and in all of South Carolina - that claim is real, and it shows in the building. It's a multi-level deal: a main dining room, the Whiskey Lounge, Henry's Music Hall, the Anson B. Lounge, and a rooftop, all stacked on top of each other across from the City Market. Live music happens nightly, the room is warm and comfortable rather than polished, and the crowd is a genuine mix of tourists and locals who have been coming in for decades.
The food is Southern and casual - shrimp and grits, jambalaya, seafood pasta, the chicken salad sandwich that one review called the best she'd ever had, and a she crab soup that keeps showing up in the good ones. The drinks lean on the classics rather than inventions: Moscow mules, Old Fashioneds, Manhattans, and margaritas all come out at a friendly price with generous pours, and the Old Fashioned made with a local whiskey is the one people remember. It's the kind of place a girls' trip ends up at three times in one trip, and the rooftop keeps a quieter corner for the people who want a break from the music.