From melt-in-your-mouth steaks to the dessert everyone should save room for, here’s what it’s really like dining at The Eight Six.

If you've tried booking The Eight Six, you already know the struggle. Reservations disappear almost instantly, but I somehow lucked out and won a table through DoorDash.
Walking in, the restaurant immediately feels like you've stumbled upon one of New York's best-kept secrets—dimly lit, intimate, and effortlessly cool. The restaurant sits inside the old Chumley's space — the Prohibition-era speakeasy where Hemingway and Fitzgerald used to drink, and where the actual culinary term "86" was born. So the restaurant is named after the phrase that was named after the building it's in. It's giving very "the snake eating its own tail" energy, except the snake is a12oz bone-in wagyu strip. I would know, because I ordered it.

The pickles arrived before I even asked for anything
Complimentary pickles, no context, no menu yet. Just: sit down, here are pickles. Bold opener. 10/10 palate cleanser before I made several very important decisions.

I skipped apps and went straight for the meat.
Bone-In Wagyu New York Strip — 12oz, Center Cut, Rosewood Ranch, Ennis, Texas — $90
This steak comes with a hometown. Not "wagyu." Not "strip steak." A specific ranch, a specific Texas town, basically a birth certificate. And it earns the introduction — deeply beefy, the bone doing exactly the flavor-insurance thing bones are supposed to do, char on the outside like it went through something and came out better for it.
Filet Mignon — 8oz, Center Cut, Jeff Huss and Family, Mitchell, South Dakota — $69
The filet is the quiet one at the table. Buttery, almost shy about how tender it is. If the strip is the friend who tells a great story at dinner, the filet is the friend who just quietly pays for everyone and doesn't mention it.
The sides were doing the most, in the best way
Creamed Corn Pot Pie — $19
A whole pie situation for a side dish. Croissant-layered pastry over sweet corn and 2-year-aged parmesan, so it's essentially a savory pastry impersonating a vegetable.
Roasted Tivoli Farm Mushrooms — $17
Sherry-au jus glaze, cured egg yolk on top like a little golden crown. Deeply savory, slightly indulgent.
Mashed Potatoes — $17
European butter, stated plainly on the menu like a threat. They were not lying. These potatoes have never met a diet in their life and I respect that.
Then things got a little theatrical
A lemon palate cleanser, served in a bowl of scooped lemon. I don't fully know what was happening but I felt cleansed, spiritually and palate-ly.
And then dessert, which I was not emotionally prepared for
Banana Trifle — Banana Custard, Vanilla Chantilly Cream, Dulcey Crunch, Nilla Crumble, Brown Butter Salted Caramel — $21
This is banana pudding that went to finishing school. Every spoonful hits a different texture — custard, crunch, cream, crumble — like the dessert equivalent of a boy band where everyone gets a solo.

Is this an expensive dinner? Yes. Did every single dish justify its own little origin story? Also yes. The Eighty Six knows exactly what it is — a steakhouse with history literally baked into the walls. Between the ranch-specific steaks, the pastry-lidded corn, and a dessert that required four different textures to properly show off, I'd go back. I'd probably order the same things.
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