We have a complicated relationship with Crabtree’s Kittle House. We love how this place oozes history, how they were name-checking local farms and rotating seasonal ingredients long before it was cool, and how the wine list will silence the biggest grape snob you know. On the flip side, you can’t always tell who’s waiting on your table, and the menu never seems to pick a lane—smoked salmon, falafel bowls, and truffled mac and cheese all make an appearance. But we keep coming back, because there are two great ways to play Crabtree: bring your parents to the stately main dining room for a civilized, grown-up meal. Or, camp out in the dark, cozy tap room that serves as Chappaqua’s unofficial living room, with live piano music, a killer veggie burger, and a huge glass of your new favorite wine.