City Winery

Summer produce gets the full dinner-party treatment at this City Winery pairing, where the menu is built around the season rather than treating it as an afterthought. The chef-winemaker format gives the evening a little more structure than a standard night out, with food and wine planned to work together course by course. For diners who usually have to choose between a serious meal and a tasting, that combination is the main reason to book. The summer focus also makes this feel appropriately timed: expect the menu to lean into the bright, fresh ingredients that are at their best right now. It is a good fit for a date or small group that wants dinner to feel like an occasion without going all the way into fine-dining formality. Come for the seasonal menu, stay for the wine, and let someone else handle the pairings.

D.L. Hughley has never been the kind of comedian to tiptoe around a topic, and that's exactly why audiences keep coming back. The longtime stand-up, radio host and The Original Kings of Comedy star brings his sharp, unfiltered take on politics, pop culture and everyday life to City Winery Boston for an intimate run of shows where nothing feels off limits. Hughley has a knack for making even the most divisive subjects feel laugh-out-loud funny, often leaving the room wondering whether they should be laughing as hard as they are. Seeing him in a smaller venue only adds to the appeal, trading arena-sized crowds for a setting where every punchline lands a little closer to home. If your favorite comedians are the ones willing to say what everyone else is thinking, you'll probably want to grab a seat before these shows sell out.

Alex Marley brings his music to City Winery for a night that should appeal to listeners who prefer their live shows in an intimate room. The venue's seated, close-up setup puts the emphasis on the songs and the performance rather than spectacle, making this a good option for actually paying attention to the music. Marley is part of a younger generation of artists working in a space that draws from reggae and contemporary songwriting, giving the set a natural fit for City Winery's more listening-focused format. If you've been meaning to catch him live, this is a chance to hear the material in a room where the details are easier to appreciate than they would be at a large outdoor show. Pair it with dinner or a drink at the venue and make an evening of it, rather than treating the concert as a quick stop.