2 Best Restaurants in Southwestern Connecticut, Connecticut

Just south of the Ridgefield town line on U.S. 7, you'll see a huge ice-cream cone on the roadside marking Heibeck's Stand, where you can choose a made-to-order burger or hot dog with a variety of toppings or a sandwich, Philly cheesesteak, lobster roll, taco, salad---even a house-marinated portobello mushroom "burger." Best of all is the ice cream, which is rich, creamy, and deee-licious—in midsummer, try the fresh peach ice cream.

Heading north from Fairfield County toward the Litchfield Hills along rural Route 53, definitely stop at the Sycamore Drive-In in Bethel for a burger, fries, milkshake, and authentic 1950s atmosphere. During the summer, Saturday "Cruise Nights" (5-8 pm) see classic cars and "hot rods" fill the parking lot (more parking across the street) and rock 'n' roll music fills the air.