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. Boxcar Cantina

    $$

    If it's Southwestern food you're craving, Boxcar Cantina delivers the freshest and most authentic Tex-Mex dishes in the area. Diners rave about the margaritas, pairing them happily with fish tacos, quesadillas, enchiladas, and burritos.

    44 Old Field Point Rd., Greenwich, Connecticut, 06830, USA
    203-661–4774

    Known For

    • Chefs take special care to source local organic ingredients
    • The restaurant has a stand at the nearby Westport Farmers' Market on Thursday
    • Takeout is available

    Restaurant Details

    Rate Includes: No lunch weekends
  • 2. Heibeck's Stand

    $

    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.

    951 Danbury Rd., Wilton, Connecticut, 06897, USA
    203-917–9313

    Known For

    • The ice cream
    • Patio dining in the back
    • Easy in, easy out, easy parking

    Restaurant Details

    Rate Includes: Closed early Oct.–mid-Apr. Closed Mon.
  • 3. 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"
  • 4. The Ginger Man

    $$

    Come for lunch when shopping along Greenwich Avenue, brunch on Sunday, dinner anytime, or just liquid refreshment, as The Ginger Man has a long, friendly bar and casual seating up front, a cozy dining room with a fireplace in back, and formal dining upstairs via a grand curved staircase. Whether you order a burger and fries, fish-and-chips, or a NY strip with roasted fingerlings, you won't leave hungry—or thirsty.

    64 Greenwich Ave., Greenwich, Connecticut, 06830, USA
    203-861–6400

    Known For

    • Burgers famously served on an English muffin
    • Relaxing, local atmosphere
    • More than 50 beers, half on tap
  • 5. 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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