Boston's Hidden Restaurants

Rawley's Drive-In

1886 Post Road, Fairfield, CT 06824
(203) 259-9023 Find location!

Photo of Rawley's Drive-In, Fairfield, CT On the surface, Fairfield seems like your typically quaint and charming Southwest Connecticut town, with tree-shaded lanes, interesting boutiques, and one of the most picturesque main streets in all of New England. But look beneath the surface and you will discover that Fairfield also happens to be a place full of classic roadside food joints, including nationally-known spot in Super Duper Weenie and hidden treasures such as Wilson's BBQ. And within a stone's throw of Wilson's is an easy-to-miss drive-in called Rawley's, which rivals Super Duper Weenie in the hot dog category, though the two places certainly have different ways of cooking them.

Rawley's is located west of the center of Fairfield on a rather plain stretch of road that runs alongside high-tension wires and railroad tracks, befitting the working-class feel of this dining spot. In a way, Rawley's has a similar feel to Blackie's in Cheshire (a ways north of Fairfield), in that it is a classic roadside stand housed in a rather forlorn-looking spot, though Blackie's is admittedly in a much more rural setting. But both reside in structures that look more like houses than commercial buildings, both have very old, dark seating areas inside (including counter seating with stools), and both feature some of the best hot dogs and hamburgers in the area.

Although Rawley's serves a handful of different items, including chicken sandwiches and burgers, the hot dogs are perhaps the biggest draw, as they are deep-fried rather than grilled (as they are cooked at Super Duper Weenie), giving them an outstanding mix of crunchiness on the outside and juiciness on the inside. They can be ordered with a number of toppings, including cheese, chili, and something called "hellish relish," which is fairly hot and very delicious, with a mix of ingredients including onions and peppers. For those who aren't looking for hot dogs, the griddled burgers here are also excellent, with the high fat content of the thin patties giving them a ton of flavor. The crispy and fresh handcut fries are also decent, and go perfectly with the burgers and dogs. One other item of note at Rawley's is the superb milkshake, which is thick and rich, yet not overly syrupy or sweet.

In a strange way, Fairfield, CT, has a bit of a "restaurant row" when it comes to snack shacks and roadside dining. Who would have thought that such a tidy, well-heeled community would have several dining spots like these? But it is indeed true, and Rawley's is certainly one of them. Deep-fried hot dogs may not be for everyone, but for those who love a little slice of Americana when they dine, this little drive-in on the western end of town is a real winner.