Restaurants in Fairfield, CT

Although the fancy town of Westport is just to its west, Fairfield’s best eats are more ballsy, like Bridgeport to the east. In particular, we’re talking hot dogs: deep-fried and griddle-crisped rippers at Rawley’s (to which Martha Stewart used to venture from her home in Westport), chili dogs topped with thermonuclear Kuhn’s chili at a Five-O convenience store where the view from its two dining tables is shelves of motor oil, and a place called Super Duper Weenie. Starting as a food truck with cordon bleu standards, S-D-W became a restaurant serving what one hates to call artisan wieners (because that term implies punctiliousness and these franks are bold and jivey) but what are, in fact, hot dog royalty. The franks and buns are locally sourced and condiments are all made in house. The S&S Dugout is one other Fairfield treasure: an inconspicuous diner, circa 1950, where roast beef sandwiches are works of art.

Fairfield’s Most Famous Dishes

Char-crust New Haven pizza topped with crushed tomatoes and a bit of grated cheese... but no mozzarella

Tomato Pie (Northeast)

Cafeteria tray holds a square meal of BBQ chicken, mac & cheese, collards, cornbread, sweet tea, and banana pudding

Dinner Platters

Extreme close-up of sausage bites in a drift of melted cheese on a thin-crust pizza

Sausage Pizza

hot dog with hot mustard and relish

Classic Hot Dogs

Fairfield’s Best Restaurants

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Great Fairfield Recipes

Mighty Ity


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