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Last summer, on a typical weekend at Surf Lodge in Montauk, Jaden Smith performed Saturday night while the surfer Evan Valiere cheered him on and Tiffany Trump and Naomi Biden posed for photos — with each other. The next day, the rapper Lupe Fiasco would draw almost 400 people at a packed, outdoor performance; some guests showed up on kayaks to watch from nearby Fort Pond. It was so crowded that the guest list ceased to make a difference.

“Last year it was politician year, all the kids,” said Alan Rish, a spokesman for Surf Lodge. “Malia Obama comes every year over the Fourth of July for her birthday.”

The Surf Lodge, a casual-chic hotel and lounge known for free concerts and its outdoor deck, attracts celebrities like Rosario Dawson and Jon Bon Jovi, as well as local fishermen and weekenders.