1 Porterhouse at The Willett House
Don’t tell your wife. Don’t tell your doctor. But do it anyway. This giant carnivorous indulgence of bone-in pleasure offers the best of both worlds: a juicy strip steak and buttery tenderloin. It arrives tipped on its platter to collect all those shamefully delicious juices. Your cholesterol will pay, but, man, is it worth it.
2 Autumn Sunset at X2O Xaviars on the Hudson
X2O is Westchester to the 20th power, offering stunning views, excellent food, and a Yonkers-born celebrity chef. If you’re looking for the ultimate at X2O, have the sugar-crusted cowboy rib-eye at the south corner table in autumn, where all around you is the Hudson River and trees exploding in color on its banks. Who knew that saying goodbye to summer could taste (and look!) so good?
3 Evening on the Patio at Bedford Post
There’s nothing so aristocratic as enjoying luxury spiced with rusticity, like reveling in a fine wine while enveloped in the scent of roasting game. This is why we love the terrace at Bedford Post. We can sit coddled in the moneyed hills of Bedford while Chef Jeremy McMillan infuses figs and orange-scented Hudson Valley chickens with the subtle, romantic flavors of wood smoke. We defy you not to feel the same.
4 The September Farmer’s Feast at Blue Hill at Stone Barns
Cheers to you if you can afford to go to Blue Hill in every season, but, for the rest of us mortals, a BHSB meal is a splurge, at best. And if you’re only going to visit the iconic restaurant once per year (or once in a lifetime), then make sure that you sit down to the Farmer’s Feast, a multi-course tasting prepared around the day’s harvest, in September when the fields are practically groaning with bounty. Don’t make any post-prandial plans and settle in for a mind-bending food ride that practically makes a fetish of farm-to-table dining.
5 Omakase at Sushi Nanase
With sushi, perfection exists in the details—and no one masters details like Sushi Nanase’s Yoshimichi Takeda. This veteran of Nobu and Masa sources his pristine fish daily, and blends his own soy sauce for subtle, umami-rich perfection. Look for rare Japanese herbs and fruits as garnishes—but remember, be respectful: Book your table and omakase (chef’s choice) dinner ahead, because no walk-ins are admitted.
Photography by Andre Baranowski
6 Pig Dinner at The Cookery
This call-ahead orgy offers the ultimate expression of pigphilia: You and five of your best buddies will commune under a mural of a pig as Chef David DiBari carves up an entire roasted pig for your delectation. It’s barbarism at its best. And, PS: Don’t skip the cheeks.
7 Tasting Menu at 42 The Restaurant
You can’t beat Anthony Goncalves’s unique brand of high-flying, molecular-Portuguese cuisine—especially when it’s paired with wraparound views from the top of Westchester’s tallest building. It’s over-the-top in every way possible.
8 Dinner and Drinks at Equus at Castle on the Hudson
Here’s the plan: If you’re going to drop the cash, get the most out of Westchester’s greatest castle. Start with drinks on the veranda that overlooks the wide expanse of the Hudson, and then dinner in the Oak Room by the stone hearth scavenged from a Scottish estate. Sure, the Castle’s ownership has changed, but it’s still as luxe as we get (and nothing beats a baller night of living like a robber baron).
9 Wine Dinner at Crabtree’s Kittle House
Age and size have their benefits, especially when it comes to wine cellars. Crabtree’s Kittle House’s cellar is so deep and wide that it’s able to offer incredible deals on its stunning wine list, making this Westchester icon one of Food & Wine’s top five “Pairing Meccas” in America.