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What started as a food truck, slinging Philly cheesesteaks outside the Best Buy in Bay Shore in 2014, now includes five brick-and-mortar locations across Long Island and Queens.
Chiddy Cheesesteaks’ newest location has just opened its doors in Oakdale.
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The new Chiddy’s is located in the former Island Empanada location, which closed earlier this year, at 1551 Montauk Highway.
Prior to that, the pretty, two-story building played host to Wild Side Organic Bistro & Bar.
Aside from its food trucks (also available for private parties), one of which parks outside CitiField for Mets games, the rapidly growing chain has brick-and-mortar locations in Commack, Farmingdale, Astoria, West Islip and, now, Oakdale.
They offer the Philadelphia staple, along with fries, but also signature sandwiches, vegetarian options, empanadas and more. Click here for the full menu.
Photo: Chiddy’s Cheesesteaks on Facebook
How the whole thing happened
Mike Chidester ventured into the cheesesteak business after almost 30 years in the corporate world, having worked in management for such big companies as Coca-Cola and IBM, Greater Long Island previously reported. But he said he had long been interested in owning a sandwich shop, and it just so happened his nickname made for a catchy business title.
“I’ve been a cheesesteak fanatic all my life. I used to vacation on the Jersey Shore, and that’s when my love for cheesesteaks came to be,” Chidester had said. “Chiddy is actually my family nickname, so a lot of people didn’t know I had a first name, Mike. They just called me Chiddy.”
At the time, hot dog trucks were the most common type of food truck on Long Island. Chidester said he decided to explore the cheesesteak concept further, adding that he felt there was a “void” in authentic Philly cheesesteaks across the island.
So, he merged the two concepts and launched Chiddy’s Cheesesteaks food truck in 2014 in Bay Shore.
After that proved immensely popular, Chiddy’s second food truck kicked off in 2017 and not long after, Chiddy’s Cheesesteaks debuted its first physical storefronts in Farmingdale and Commack, six months apart in 2018.
Chidester said instead of continuing to put more food trucks on the road, he decided the future of the company lay in brick-and-mortar restaurants.
The wheels really started turning for the business during a discussion over beers between him and two buddies.
“We joined forces, and once we decided we really wanted to explore this opportunity, I think that day we jumped in the car and started looking for spots,” Chidester said.
They also offer franchise opportunities. Scroll down to follow their journey on Instagram.



















