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Chesterton Tribune
The Port Drive-In is 50 years young
by Kevin Nevers
March 30, 2007

The old license plates, the roller-skating waitresses, the tin signs advertising Hudson Hawks and other classics: The Port Drive-In is a nostalgic celebration of the car culture of the ‘50s and ‘60s, of a simpler, more innocent time, if not in fact at least in our hearts.

Yet for two generations of Dunelanders a trip to The Port conjures a much more personal nostalgia: for hot beach days and lazy summer nights, first dates, hanging out, ice cream sodas after Little League, a youth spent in the shadows of the steel mills and on the shores of Lake Michigan.

For half a century the Gassoway family has been making memories, ever since Elsie and Virgil Gassoway bought a drive-in restaurant at 419 N. Calumet Road from a man named Studtman in 1957.

Elsie and Virgil brought their German work ethic to the business—and their German recipe for chili—and they prospered. Then they retired and in 1978 sold The Port to their son Terry and his wife, Beth.

Over the years the menu has grown and shrunk. When Roman Catholics let meatless Fridays go by the wayside, the Gassoways did the same with tuna and egg salad sandwiches. For awhile the Gassoways offered a soup and salad bar but later abandoned the experiment as impractical. Meanwhile, the hamburgers have increased incrementally in size, by a quarter pound, then a third, then a half. And if you’ve got a taste for it—and many do—you can order yourself a fried pickle.

Other things have changed as well. In the old days The Port was just a drive-in with no indoor seating. In 1976 the Gassoways added the dining room and hard though it may be to believe now—it was the ‘70s after all—they decorated it in wicker and green plants. Now, too, the waitresses may roller-skate, or they may roller-blade.

But the more things change, the more they stay the same. “What’s important for us is to try to maintain the old-fashioned feel,” Beth says. “You need to give customers a good value to keep them coming back. But we also have to keep it fun. It’s a drive-in. It’s supposed to be fun.”

Take the menu. At the moment it’s huge, with everything from phosphates, sundaes, and floats, to chicken, shrimp, and clams. And even if you’ve never eaten at The Port, chances are good you know at least some of the menu items. Put some smelt under your belt. Tacos two for one, Muy Bueno.

But it’s the chili, liberally spread on hot dogs and fries, that truly links the present to the past. It’s still made from scratch on the premises according to Elsie’s recipe. So’s the root beer, home-brewed in specialized equipment to give it a flavor and body unobtainable anywhere else. “Terry’s our chili master and he’s our brew-master too,” Beth says. “These are our signature items. They’re unique products. We’re known for them.”

The Port is known for something else too: the hundreds of Duneland teenagers who found their first jobs serving and cooking there. “‘Where do you find these nice young girls to waitress?’ people ask all the time,” Beth says. “We get a lot of compliments. I can’t take much credit for that. They’ve been raised at home to be nice and polite. We’re really like a family here. We’ve even had second-generation employees.”

And then there’s the sign out front, its chit-chatty teasers constantly changing, advertising specials, welcoming regulars, and—one of the surest signs of spring in Duneland—announcing the season opening. “‘We couldn’t wait for you to open. We were watching your sign. We knew it would be soon.’ We hear that every spring,” Beth says.

Not only Dunelanders, though, flock to The Port when it turns green and warm. “We have a tremendous following from Chicago, Indianapolis, all over the country,” Beth says. “When they go to the National Lakeshore or the State Park for a vacation, they always stop here. People come off the Interstate. This is part of their Dunes experience. I find that heart-warming.”

And it’s always been that way. “We used to have a big map of the U.S. on one of the walls,” Beth says. “We’d ask customers where they came from and we’d give them a push pin to stick in their hometown. We had customers from every state and a dozen foreign countries.”

For Beth the interview is a chance to take a nostalgic stroll of her own. She recalls how once upon a time a young man and woman chose The Port for their first date. A year later he popped the question to her on the sign in front. She accepted, as the entire staff, having conspired in the proposal, watched from inside. Beth knows of another couple who return twice every year with their daughters and sit in the same booth where once and then a second time they sat to celebrate news of the stork. So The Port isn’t simply an institution in Duneland. It’s an intimate landmark in many Dunelanders’ lives.

Last year The Port Drive-In was presented with a Governor’s Half Century Business Award in honor of its longevity. “That was a very pleasant surprise,” Beth says. “We just do what we do and to be recognized for just plodding along was pretty nice.”

Plodding along may not be the best way of describing the Gassoways’ business philosophy but it does capture something of their commitment to tradition. “The way we do things, when we do things, has evolved because it feels comfortable to us,” Beth says. “We do it our way because that’s the way we’ve always done it.”

The Port Drive-In is open seven days a week during the season from 10:30 a.m. to 9 p.m. Complete carry-out service is available. Call 926-3500. And visit The Port’s website at www.theportdrivein.com.

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