Rick's Crabby Cowboy in Montauk Wins Best of the Best Award From Pilots Group

Rick’s Crabby Cowboy, situated off East Lake Drive in Montauk, might be in the ideal spot for a stroll on the beach or a walk to the docks after dinner—but its proximity to the Montauk Airport is what’s earning the restaurant some serious wings.

The BBQ/seafood joint was named this year’s Best of the Best by a Florida-based pilot association, $100 Hamburger. The group, founded by John Purner in 1994, is made up of more than 54,000 private pilots who subscribe to the organization, all in search of the country’s best “fly-in” restaurants.

In order to be considered for the Best of the Best award, said Mr. Purner, restaurants must be in walking distance of an airport and be rated five stars by members of the $100 Hamburger organization. Members of the group submit their top picks for Best of the Best, and the favorites are compiled and published in the annual $100 Hamburger book, which breaks down restaurants by state, airport manager, runway length and width, and a brief descriptor of the restaurant with operating days and hours.

“We’re at the very end of the runway,” said Rick’s Crabby Cowboy owner and chef Rick Gibbs. “Some people in East Hampton complain about airport noise, but for us it’s been great. People love the excitement of watching the planes take on and off. And a lot of people that come here to eat, come by plane.”

The notion of “fly-in” dining, especially during the height of summertime in the Hamptons, may render an image of Jimmy Choo-clad women on the arms of Manhattan’s most successful investment bankers, shuffling across the airport runway to one of the area’s most exclusive restaurants. But Rick’s Crabby Cowboy is anything but that.

“This is the epitome of a summer place,” said Mr. Purner in a phone interview. “It’s a great little seashore kind of place. And the food is incredible. It’s not Lower East Side Manhattan food. But it’s the perfect place to bring your family.”

Mr. Gibbs, who started the restaurant 19 years ago, said the Crabby Cowboy prides itself on being family-friendly, approachable, and an all-around good time, offering volleyball games on the beach, a fire pit and DIY s’mores.

“We’ve got everything from minivans to Maseratis in the parking lot,” laughed Mr. Gibbs.

And despite its name, the $100 Hamburger organization is far from being in pursuit of, quite literally, a $100 meal.

Rick’s Crabby Cowboy menu includes clam chowder, steamers, muscles, all for less than $12, and entrées like BBQ ribs, pulled pork, crab cakes, and grilled tuna, are all less than $25.

“There are times … you wanna just throw on your favorite pair of jeans and eat a burger. Rick’s is that kind of place,” said Mr. Purner. “It does a better job of being that place than any other place that we know about in the Northeast, because of everything it brings to the party. It’s at an airport, it has its own marina, there’s a beach there, there’s wonderful food there. You can watch the lobster boats deliver it—you can’t get a fresher lobster than one right off the boat.”