Annual 2025 CityScope® Summer Issue
By Tory Irmeger / Photography by Kristina Armstrong
For some, the roaring of a train along its tracks might be considered a nuisance. At Ooltewah Whistlestop, however, it’s all part of the experience, harkening back to an era when railways defined and connected Southeastern communities.
Situated along Main Street, Ooltewah Whistlestop is a themed café offering comfort eats and iconic sweet treats. The owners, Melissa and Josh Cain, chose Ooltewah 14 years ago as the place to raise their family. “We have devoted much of our time and efforts into maintaining the hometown integrity of Ooltewah,” they share. “Keeping to Ooltewah’s original roots, we decided after extensive research, travel, and thoughts that the Ooltewah Whistlestop was exactly what was missing in our community.”
From the outside, one might guess that the building is original, but the flatiron-shaped restaurant is actually a tribute to the Ooltewah passenger depot. The Ooltewah Depot was built in 1882 along the “Ooltewah Cutoff” line, which connected Chattanooga and Atlanta by way of Ooltewah to Cohutta, GA. The depot closed in 1976 and is no longer standing. “Paying homage to the original depot located directly beside the railroad tracks, we decided to create the Whistlestop with it in mind, keeping as many vintage aspects as possible,” says Cassie Quintard, restaurant general manager.
From wall to wall, the Ooltewah Whistlestop immerses guests in a nostalgic design reminiscent of a mid-century diner. Brassy light fixtures punctuate a row of booths, while barstools at a garage-style window provide front-row seats to the trains rolling by. On the hike up to the rooftop patio, guests on the stairwell can view a gallery wall of vintage photos from bygone days.
Meanwhile, the menu is as full of charm as the décor. Classic fare of sandwiches and small bites earn rock ’n’ roll titles like “Good Golly Miss Molly Grilled Cheese” and “Jailhouse Rock Roast Beef.” If guests have saved room for dessert, they’re in for signature milkshakes piled high with candy, snack cakes, Tasty Donuts, whipped cream, and even whole slices of cake. These larger-than-life creations are a feat of engineering, winning the awe and delight of customers of all ages. Specialty milkshakes rotate throughout the seasons, including concoctions inspired by Shark Week, the U.S. Open, and the “Harry Potter” franchise. For folks who prefer to keep it classic, there are malts, floats, and even a “Boogie Woogie Bugle Boy Banana Split.”
Quintard describes the atmosphere of Ooltewah Whistlestop as “nostalgic, family-oriented, and fun.” The café celebrates local history and offers a place for friends and family to gather, celebrating life milestones or simply enjoying a summer night. She adds, “Each time a train passes, customers – regardless of age – light up and get so excited.” Although the trains no longer pick up passengers at the Ooltewah Depot, guests at the Ooltewah Whistlestop can imagine what it would be like to step back in time – all while enjoying a monumental milkshake. These exceptional treats reflect the heart of the café: good food and good memories are to be shared.
