Stop by newly opened Little Red for grilled cheese with brie, slow-roasted duck, braised cabbage, and Dijon ($24) paired with one of their local wines on tap, like Paumanok Chenin Blanc ($12), made on the North Fork in Aquebogue. The red-and-white interior is filled with abstract oil paintings by local artist Mark Humphrey, whose gallery is on Main Street, and you can also grab an order of fish and chips ($26) to enjoy lakeside in nearby Agawam Park.
Choose from five options (from $11), including vegan and mako shark, prepared by James Beard nominee Alan Hughes at the new Banzai Burger. Or order from the sushi bar, where chef Isao Yoshimura turns fluke and black sea bass he catches himself into sashimi ($17). After dinner, drink $4 PBRs and play a game of pick-up ping-pong in the gravel courtyard.
Try to get a table at the new Southampton outpost of Sag Harbor’s popular Tutto Il Giorno (56 Nugent St.; 631-377-3611), where you can enjoy refined dishes like whole branzino served with a fennel and cherry tomato relish ($33). Part-owner Gabby Karan De Felice (daughter of Donna Karan) designed the modern space, filling it with paintings from local artists and some from Haiti as a nod to her mom’s initiative to support the country at her Urban Zen shop in Sag Harbor.