The Five Hundred-Dollar Hamburger

An aviation tradition becomes a bucket-list project for a father and daughter.

“Here, hold the stick for a second while I take a picture.” My dad is already turned to the left, camera in hand, snapping photos of the scenery gliding by 3,000 feet below us in his Cessna 172. My stomach dips. I’m not a particularly nervous flier, but I want no share of the responsibility for actually keeping the plane in the air.

He turns back before I can protest. “No? You know, I could drop dead up here; then you’d have to learn to fly this thing real quick,” he says. That is my dad: dark sense of humor; no sympathy for the tightly wound. “Maybe some other time,” I say, trying to keep my knees as far away from anything resembling a control as I can. “How about I take the pictures instead?”

We’re somewhere over central Virginia, on our way to the next town over for pizza. It’s questionable whether this pizza is any better than the pies we can get in my hometown of Charlottesville, Virginia, but I'm home for the holidays, the weather is beautiful, no flight students have rented his plane for the day, and we both want an excuse to get out of the house. And so, here we are, at an altitude where the entire landscape looks like one sprawling scale model, floating over glittering lakes and the long snaking thread of I-64.

Hopping in a plane for a meal and an afternoon flight is a common practice among those who fly for fun; in aviation slang, it’s known as a “hundred dollar hamburger,” since by the time you factor in the cost of plane rental and fuel, you’re paying a rather high price for your lunch. Trips like these are excuses for afternoon joyrides as much as they are a way for a pilot to keep his skills sharp.

The practice is so popular it’s spawned a website and a book with multiple editions (both authored by private pilot John Purner), essentially Zagat guides to airport restaurants. When my dad got his pilot’s license in 2003, we adopted the tradition as our own. It’s a good way to fritter away an afternoon together doing something we’re both very passionate about—flying (him) and eating (me)—without having to do too much actual talking (we’re a family of introverts).

Traditionally a hundred dollar hamburger involves eating at an on-site airport restaurant. But we prefer to go exploring instead, taking advantage of the courtesy car that most small airports lend you after you land. We keep a list going of the spots we want to visit, and over the years it has accumulated restaurants faster than we can check them off: a beautiful seafood place on the water in Stonington, Maine; a crab shack in Stevensville, Maryland; a fine-dining gem unexpectedly situated in a small town in Virginia.

If flying commercial has turned into something of a horror show, then a spin in an ultralight is the antidote; it restores every bit of the magic that’s been lost in the security lines, endless fees, and cramped seating of a commercial flight and allows the full force of what flying really is to hit you: you’re in a machine, invented by man, which transports you across great distances while suspended in the air. Adding an incredible meal to an experience like that makes the whole trip that much more unforgettable.

8 Great Destinations for a Hundred Dollar Hamburger

While my father and I are just as likely to fly to a hole-in-the-wall takeout joint as a white-tablecloth destination restaurant, it’s easier than ever to turn an afternoon jaunt into a luxe dining experience—chasing lower rent and more intimate relationships with farmers, more and more talented chefs are deserting large cities in favor of smaller towns. Here, our picks for the best restaurants to seek out, all within driving distance of regional runways on the East Coast. Because some are only open for dinner—and just because it’s fun to make a weekend of it—we’ve included recommendations for where to stay in some cases, too.

Chef and the Farmer
Chef Vivian Howard, the subject of PBS’s multi-part documentary and cooking series A Chef’s Life, opened this spot in eastern North Carolina in 2006 with her husband Ben Knight. Expect innovative dishes heavily focused on local ingredients and techniques, like rice-crusted catfish with charred collard slaw and ramp remoulade and pan-roasted Cornish game hen with sorghum grain salad and buttermilk sauce. The restaurant is only open for dinner, so go early—or make a weekend of it and stay at the Fearrington House Inn (rooms from $350; 2000 Fearrington Village Center, Pittsboro, NC; 919-542-2121), a Relais & Chateaux property that’s a 45-minute flight away. 120 W. Gordon St., Kinston, NC; 252-208-2433;

The Shack
The late food writer Josh Ozersky put this tiny restaurant in Staunton, Virginia, on the national map in 2014 when he declared it the food writer’s—and food traveler’s—Holy Grail: or as he put it, in Esquire, “The Incredible Restaurant in the Middle of Nowhere that Nobody Knows About.” Chef Ian Boden is certainly doing some creative cooking in this 26-seat spot at the foot of the Blue Ridge Mountains; expect dishes like chilled lettuce soup with goat’s milk yogurt, olive oil croutons, boquerones, and onion blossoms and roast chicken thighs and benne dumplings with spring vegetables, mushroom, and bacon dashi. If you’d rather linger and not fly home, Frederick House, a charming 23-room inn in downtown Staunton (rooms from $135, 28 N. New St, Staunton, VA; 540-885-4220;, is the closest option, or Keswick Hall (rooms from $374; 701 Club Dr., Keswick, VA; 434-979-3440;, a resort set on a 1912 country estate, is about an hour to the east. 105 S. Coalter St, Staunton, VA; 540-490-1961;

Bartlett Pear Inn
After working under Michel Richard at Citronelle, Thomas Keller at Per Se, and Christian Delouvrier at La Goulue, chef Jordan Lloyd returned with his wife Alice to their hometown of Easton, Maryland, to open the Bartlett Pear Inn in 2009. Their 30-seat restaurant sits on the first floor of the boutique property; you’ll find a menu full of subtle updates of classic Chesapeake dishes and Eastern Shore ingredients, presented in three-, five-, or seven-course tasting menus with optional wine pairings. Stay the night in one of their seven rooms. Rooms from $234; 28 S. Harrison St, Easton, MD; 410-770-3300;

Crystal Springs Resort
You might not expect one of the best wine cellars in the country to be located in northern New Jersey, but the restaurant at this four-season resort in Hamburg has a cellar that’s staggering in its quality and quantity. The late owner of the resort, Gene Mulvihill, set out to build one of the best wine cellars in the world, and wine director Robby Younes and sommelier Susanne Lerescu have continued on that path, amassing more than 135,000 bottles—including more than 100 vintages of Chateau Latour, a personal favorite of Mulvihill and the namesake of the attached restaurant. While the tome of a wine list (so large it’s delivered on an iPad) is full of rare, hard-to-find (and expensive) vintages, Younes and Lerescu have an equal affinity for affordable wines and wines from small producers and lesser-known regions. Taste your way through a vertical of Domaine de la Romanée-Conti or try a $20 organic/biodynamic zinfandel; either way, you’ll want to make a night of it: book the Fireplace Deck Suite at the property’s Grand Cascades Lodge. Rooms from 399; 1 Wild Turkey Way, Hamburg, NJ; 866-348-0958;

Blue Hill at Stone Barns
Chef Dan Barber’s restaurant, situated at the Stone Barns Center for Food and Agriculture in Pocantico Hills, New York, is a dining destination for people all over the country, and it also happens to be just a 20-minute drive from the Westchester County airport. Open since 2004, Blue Hill—a staple on the World’s 50 Best Restaurant list and James Beard Award winner—has been long lauded for its innovative menu that showcases the farm’s bounty and the terroir of the lush Hudson River Valley. It’s famously difficult to snag a reservation, but once you do, expect to be spoiled with a tasting menu that’s as many courses as you want it to be. Stay at the nearby five-star Castle Hotel and Spa (rooms from $310; 400 Benedict Ave, Tarrytown, NY; 914-631-1980; 630 Bedford Rd, Pocantico Hills, NY; 914-366-9600.

Prairie Whale
Restaurateur Mark Firth (the “Mar” of Marlow & Sons) famously left New York—and the Brooklyn restaurant empire he built with Andrew Tarlow—for Great Barrington, Massachusetts, in 2009. The plan was to set up shop as a farmer, but it wasn’t long before he began to miss the restaurant world and opened up Prairie Whale a few years later. The food is of the same ilk as the restaurants Firth helped open in NYC—rustic and made with lots of local ingredients and simple techniques. Think deviled eggs with trout roe, brick chicken, and escarole salad. They are open for brunch on the weekends, as well as dinner Thursday through Monday. Stay at the Wheatleigh (rooms from $815; 11 Hawthorne Rd., Lenox, MA; 413-637-0610; in nearby Lenox. 178 Main St., Great Barrington, MA; 413-528-5050.

Twin Farms
Though it’s not a quick drive from the nearest airport, this luxury resort nestled in the Vermont mountains is worth the 40 or so minutes you’ll spend getting there—and with everything from cycling to fly fishing to keep you occupied, a wine program featuring over 15,000 bottles, and menus customized to every guest, you’ll want to stay a while. All meals and drinks are included, and the kitchen staff takes into account each guest’s culinary preferences to create a custom menu tailored to each person. All-inclusive rooms from $1,500; 452 Royalton Tpke., Barnard, VT; 802-234-9999;

Situated right on the water in picturesque Stonington, Maine, Aragosta serves refined, locally focused fare like Taunton Bay oysters, grilled ribeye with Maine potatoes, and, of course, whole local lobster. Chef Devin Finigan worked under Thomas Keller and Dan Barber before opening the spot in 2013; go for a flight and lunch (they’re open for lunch Wednesday through Sunday) or make a weekend of it and stay at nearby bed and breakfast Blue Hill Inn (rooms from $220; 40 Union St., Blue Hill, ME; 207-374-2844; 27 Main St., Stonington, ME; 207-367-5500;


Photos: Laura Sant; Lyndsay Cayetana Bouchal / Laura Sant​; Courtesy Twin Farms Resort and Spa