For New Years, we’ll usually rent a house in Round Hill. We have friends who go to the Rockhouse Hotel but the two are like the Lower East Side versus the Upper East Side: Rockhouse is much cooler; Round Hill is pretty square—very old school, 50s, not hipster at all—but that’s why we like it. You get these old houses that are literally from the Poolside with Slim Aarons book. This place has its own clear identity that is luxurious, but also super homey. The people and the food are still very much their own culture.
Sometimes we’ll play tennis, but usually everyone just flips and reads books, hangs out at the pool, drinks beer, and takes naps. We’ll also order Dark ‘N’ Stormies, which are really strong and delicious. The place is weirdly super full service so we’ll refer to this amazing old guy, Kingsley Blake. He wears this turquoise black lapel tuxedo jacket and has been there forever. He’s known everyone who has ever gone there and is this amazing grandpa of the whole spot.