Southwestern Connecticut Restaurants

We’ve compiled the best of the best in Southwestern Connecticut - browse our top choices for Restaurants during your stay.

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  • 1. Sycamore Drive-In

    $

    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.

    282 Greenwood Ave., Bethel, Connecticut, 06801, USA
    203-748–2716

    Known For

    • The "Dagwood Burger" with everything on it
    • Eat inside or in your car
    • Saturday "Cruise Night"
  • 2. The Stamford Diner

    $$

    The menu at this art deco–style diner, alive with bright colors and shiny chrome, runs the gamut from griddle cakes to smoked salmon Benedict at breakfast, classic sandwiches to Greek specialties at lunch, chicken in a basket to rib-eye steak at dinner—or anything you'd like at any time of day or night. If that's not enough, the diner hosts occasional musical, comedy, and kids' events.

    135 Harvard Ave., Stamford, Connecticut, 06902, USA
    203-348–7000

    Known For

    • Classic diner menu—v-e-r-y long and varied
    • From early-morning breakfast to late-night dinner—every day
    • Family-friendly atmosphere
  • Recommended Fodor’s Video

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Recommended Fodor’s Video