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The longtime owners of a landmark Chesterton drive-in, one of only a few left in Northwest Indiana, are looking to sell so they can retire.

Terry and Beth Gassoway want someone to take over The Port Drive-In Family Restaurant, where carhops have served chili dogs and frosty mugs of root beer at 419 N. Calumet since 1953. They've been running the vintage eatery, where you can wash down a half-pound burger or pork tenderloin with a shake or a Green River pop, since 1978, but Terry Gassoway turns 70 in May.

This is likely to be their last season.

“We’re second-generation owners, but we don’t have a third generation,” Beth Gassoway said. “We hope he can retire by his birthday, but we need a successor, someone who will carry it to the next level.”

The Gassoways hope to sell the drive-in, including family recipes for chili and root beer, to someone who will keep it going as a restaurant and not just tear it down and turn it into a pharmacy or strip mall. They say The Port is still thriving, drawing in loyal regulars and tourism traffic from the nearby Indiana Dunes.

The Port is one of the few remaining Region drive-ins, along with Carlson’s in Michigan City and the Blue Top in Highland. It’s been a Chesterton institution where many high school kids work their first jobs.

“There are so many memories,” Beth Gassoway said. “They’d have squirt gun fights when it would get hot in the kitchen. It could be a nonstop party atmosphere.”

The staff is known for being very friendly, and often has the orders of regulars memorized.

“It’s a fun place,” she said. “People come from the beach in shorts or swimsuits, and sit in their car or listen to the jukebox. I like it when the windows are open and you can hear the motorcycles roaring. It’s like being invaded by a motorcycle gang. It’s the sound of summer.”

The Gassoways have tried to maintain an authentic drive-in experience and a nostalgic atmosphere, and say they’ll miss the place where they spent so many summers.

“My husband has root beer in his veins,” she said. “He’s the one who makes it. We wish we could run the place as a mom and pop for another 40 years, but the reality is we’re not bionic and age is setting in.”

Anyone who’s interested in purchasing the Port Drive-In should call Century 21 real estate broker Terry McCaleb at (219) 945-6965.


Business Reporter

Joseph S. Pete is a Lisagor Award-winning business reporter who covers steel, industry, unions, the ports, retail, banking and more. The Indiana University grad has been with The Times since 2013 and blogs about craft beer, culture and the military.