Each year, those things change. A Thanksgiving dinner in 2015 featured a 2-carat emerald-cut diamond engagement ring hidden in the stuffing at the base of the turkey — which one customer used to propose to his girlfriend at the restaurant. This year's dinner instead features four tickets to Hamilton, limousine service, a two-night luxury suite overlooking New York City's Central Park at the Mandarin Oriental, a $7,500 shopping spree on Fifth Avenue and a watch from Swiss manufacturer Ulysse Nardin that costs more than $20,000.
While a list like that sounds gimmicky, I realize that's not why Sherry finds so much joy in offering the world's most expensive Thanksgiving experience. Like myself, he's a Thanksgiving person.
"I'm in love with the holiday. I'm in love with the creativity of a $76,000 dinner. I'm proud of my staff and the way they put it out," Sherry says, adding that his team spent a couple months putting the experience together last year before seven customers bought in. "I love seeing the people buy this, I love seeing the expression on their face."
As I pushed the final plate away and re-contemplated Thanksgiving as a holiday, I realized something was missing — the faces of my friends and family around the table.
While my mother cooks stuffing out of a box, I look forward to it every year. It's tradition. Just like the tradition of Thanksgiving extravagance Sherry and his brother Greg have created at the restaurant they've co-owned together since taking it over from their grandfather nearly 50 years ago.
And while the whole thing seems expensive at $76,000, I can't argue that the night won't create memories. Nor can I say I wouldn't want to eat at the Homestead Thanksgiving table again if I am lucky enough to have the chance.
Maybe your table, like mine, lacks imported meats from around the world or thousand-dollar bottles of liquor. But that's perfectly fine if you realize — even at the end of the priciest Thanksgiving experience in the world — that sharing the experience with loved ones matters more than the extravagance or the price of the food that rests on top.
—Video by CNBC's Mary Stevens and Nate Skid.