Back in August, we made a reservation at Blue Hill at Stone Barns for dinner with our friends. You have to call exactly two months before the date you want to reserve. Don't plan anything else for the evening - dinner will take no less than 4 hours and 5 or 6 if you take it slow! And bring the credit card where you get the most points (read: it's not cheap). There's no menu - you pick whether you want 5, 8, or 12 courses. You'll eat a lot, but so much of is impossibly fresh vegetables, so you actually feel quite healthy leaving.
The original Blue Hill opened in in the Vilage in 2000 (and it's where Jennifer Aniston got engaged this year!) but the Stone Barns outpost, which opened in 2004, is an agrarian paradise an hour north of the city. Go before your reservation, because you can see the incredible farms and fields where most of your dinner will come from. All of the structures are on the old Rockefeller estate, which lends a very cool mid-century vibe. I really want an inn to open and think it will one day.
Andy and I love the Hudson River Valley, so we made a whole day of it before dinner and tried to see some things we haven't done before, like the Walkway over the Hudson, an old railway bridge turned awesome 1.28-mile walk over the river. Millbrook Winery has a great tour, wine tasting, and views of the valley, and downtown Millbrook is super cute. Some of my favorite places for lunch are Gigi Trattoria in Rhinebeck or the super casual Apple Bakery & Cafe at the Culinary Institute of America.