There are some great spots nearby that will surprise you, if you haven’t been (or even if you have). Best of all, you don’t have to go through TSA to get there!
Bethel
From Bethel’s central shopping area clustered around PT Barnum Square—try La Zingara for delicious Italian (also the upstairs Ecco bar); The Relay for books and character—you can venture out for independent cinema, a hip cultural scene, and one of Connecticut’s loveliest little postcard images: the Sunday River Covered Bridge. This place has hidden spots everywhere—and it’s on Metro-North, as well.
Pound Ridge, NY
Take Route 124 from New Canaan to this little hamlet—its cheese shop, small bookstore, diner (Blind Charlie’s!!!), Restaurant Jean-Georges, quirky antiques and tools spot, and home décor vendors are great. From summer-December, there’s a Sunday Farmers Market; a Summer Fine Arts Fair and a Harvest Festival during appointed weekends, too.
New Haven
Haven’t “done” New Haven yet? Why not? The Yale area of town explodes with culture (bookstores, cafes, shops, museums and libraries—all world-class), and the pizza is famously exquisite: Sally’s, Pepe’s and Modern (“Apizza” with “Muzz”). But for pastry, don’t forget Libby’s; for coffee, try Willoughby’s; for vegan/vegetarian, try Claire’s; and to test your sweet tooth, try Sugar Bakery—their cannoli cupcakes beat Bobby Flay’s.
The Bronx
As far as NYC boroughs go, the Bronx is closest, and usually overlooked, though Arthur Avenue packs people in. Not only does it have a zoo and the Botanical Gardens, but the Bronx also features the Edgar Allan Poe Cottage, a culture trolley (Wednesdays), and the 150-year-old Woodlawn Cemetery, one of the nation’s most majestic—final resting place of Duke Ellington, Herman Melville and F.W. Woolworth, to name a few. Oh, and don’t forget to tour Yankee Stadium, the (re-built) House That Ruth Built.
Milford
I like Milford because, apart from its proximity, its Town Green is HUGE, often hosting great events. In addition, there’s the eclectic, fabulous menu at Café Atlantique (OK, and the Main Cup for soup, and Colony Pizza), and the bookstores, such as Collected Stories, and the gigantic Barnes & Noble. There’s great shopping, and a walkable shopping district, as well (the Metro-North is convenient).
Kent
Driving up Route 7 is a joy, and Kent, when you stop there, will take your breath away, especially if you like antiques and all things vintage. This place is a jewel box, perfect to drop the car off in, wander through—shopping, eating and relaxing. It’s Litchfield County, so you may bump into a celeb (especially an author, particularly on weekends), so have that iPhone at the ready. Spectacular.