Best Bites: The Gray Goose

Right around the corner from Southport Center, across from the Delamar Hotel, is The Gray Goose. Under the same ownership as Westport’s Spotted Horse and Fairfield’s The Chelsea, this environment has a similar comfortable ambiance.
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Best Bites: Bodega Taco Bar

In the plaza across from Chef’s Table in Fairfield Center is a small taco bar known as Bodega. The environment appears to be urban and hipster and is solidified by the trendy soundtrack. Their guacamole is on par with some of the best I have had in my life.

Best Bites: 55 Wine Bar

Right near the Fairfield Train Station is 55 Wine Bar. Their wines by the glass are quite good and pair well with their Mediterranean cuisine. They have a country club-like atmosphere with high ceilings that make it perfect for an upscale date night. In the warmer seasons, outdoor seating is available. Although the inside is so elegant you will most likely want to dine indoors.
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Best Bites: Spotted Horse

The Spotted Horse is right around the corner from the center of Westport. The bright orange awnings are the only aspect preventing one from mistaking it for a house. The interior resembles a barn with wood, playing a major role in its décor. It has a cozy atmosphere and the staff is warm and inviting to match.

Best Bites: Post 154

Before 154 Post Road East morphed into a restaurant called Post 154, it was Westport’s historical post office. Now newly renovated, the atmosphere of Post 154 is one of the classiest in town. In the evenings there is a valet service that is particularly convenient and adds to the upscale ambiance.

Best Bites: Tarry Lodge

Located just off the Saugatuck River in Westport is your destination for excellent Italian-inspired cuisine. The environment is casual while the menu is on the formal side. As a Mario Batali partnership, you can imagine the quality of the dishes. The pizza makers are especially talented. Their oven heats up to over 700 degrees, causing their perfect pizzas to cook in just 90 seconds. If you have been to Italy, your palate will not be able to decipher pizza from here or from San Gimignano.

Best Bites: The Dressing Room

Tucked behind the Westport Country Playhouse is your home away from home. The Dressing Room is the first farm-to-table restaurant in Westport, opened in 2006 by chef, cookbook author and food activist Michel Nischan and actor Paul Newman. They support a movement for sustainable food and their mastery of comfort food makes this restaurant the ideal fall destination.

Best Bites: Pane e Bene

If you are a fan of authentic Italian food and the classic white tablecloth atmosphere that often comes with it, Pane e Bene is your new spot. It is incognito from the street and I have managed to drive past it several times and consequently had to turn around. Nonetheless, once inside, the large windows and relaxing scene manage to clear the mind. But getting down to what you need to know: The food is tremendous.
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Best Bites: Cru

Located underneath the Gap in Westport center, Cru, which opened in June, is a restaurant and lounge with a modern and luxurious atmosphere. The dining room tends to fill up because of its popularity; therefore I recommend making a reservation. The lounge is an excellent area to have drinks and small plates, and dishes are paired with recommended wines.