8 Best Restaurants in Southwestern Connecticut, Connecticut

Locals come here for outstanding oysters and the freshest fish in town; expect an especially lively crowd on weekends. Menu standouts include the fresh oysters, of course, along with classic lobster rolls, and fish tacos.

Mainly a chophouse, where you might choose a 40-ounce Tomahawk steak, 10-ounce filet mignon, double-cut pork chop with a choice of sauce or herbed butter; but the rather extensive menu also includes grilled fish, burgers, and several small plates. 

A modern take on a classic (and classy) French bistro, you'll find the usual French standards on the menu like steak frites, along with international dishes such as Madras lamb curry, Peking duck, and San Francisco cioppino. As for decor, you'll find potted palms, ceiling fans, a partially open kitchen, and floor-to-ceiling windows in the bright, airy dining room.

Enjoy a full view of the waterfront while partaking of USDA Prime dry-aged steak, chops, or seafood with classic steakhouse sides and enhancements such as horseradish cream, Bearnaise, blue cheese, or Bordelaise sauce. Start with a selection from the raw bar, wagyu meatballs, octopus carpaccio, or caramelized figs, among other options—and end with a "movie theater" sundae.

The theme for this neighborhood favorite is horse, of course; the atmosphere reflects the historic building (circa 1808), and the menu offers old-fashioned comfort foods with modern flourishes. The grilled pork chop has a whole-grain mustard glaze, chicken Milanese includes a side of lemon yogurt sauce, steak frites comes with Parmesan fries—and items on the Pony Menu will delight the kids.

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.

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.

Within the Terrain garden store, you'll find a bright, cheery café that offers exquisitely prepared dishes using locally sourced organic produce so fresh you'll want to become a gardener yourself. Enjoy brunch all afternoon; dinner entrées like line-caught Atlantic halibut with barley risotto or the duck breast with braised endive come with a delicious (and, frankly, adorable) terracotta pot of baked bread.