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Located between Boston and New York, Connecticut is the third smallest state in the U.S., stretching just 100 miles east to west and 60 miles north to south. Driving across its varied landscape takes about two hours, transporting travelers from country roads and estates to seaside towns and lighthouses.

In the northwest corner of the state, colonial villages dot farmland and the Housatonic River curves past the Appalachian Trail. The peak foliage season runs from early October to early November, when rolling hills throughout Litchfield County turn bright with fall color. In Woodbury and Putnam, antique aficionados shop storefront boutiques specializing in period furnishings and art. Hopkins Vineyard in New Preston serves 11 varieties of wine in its tasting room, tucked inside a red barn overlooking Lake Waramaug.

The capital city of Hartford, home to several insurance-company headquarters, is nicknamed the Insurance Capital of the World. Suits and ties aside, visitors to the city can unwind at the first public park in the U.S. or tour the homes of literary legends Mark Twain and Harriet Beecher Stowe.

Forest covers approximately 60 percent of the state, and outdoor activities abound, from freshwater fishing in the Litchfield Hills to hiking in Gillette Castle State Park, rafting on the Housatonic and camping on the Appalachian Trail.

At the mouth of the Connecticut River sits the village of Old Saybrook with its antique shops, eateries and old-fashioned soda fountain. In Mystic, a seaport town just 30 minutes away, visitors can explore Connecticut’s seafaring history at the maritime museum with a recreated 19th-century village, historic vessel cruises and a preservation shipyard. For a mealtime break, Abbott’s in the Rough in Noank—just five minutes from Mystic—makes a traditional Connecticut lobster roll, served hot and topped with drawn butter.

Home to Yale University, New Haven brings urban life to Connecticut with a burgeoning scene of notable restaurants and theaters, such as the Yale Repertory Theatre and the Shubert Performing Arts Center. Visitors can also stroll through prominent galleries and museums, including the Peabody Museum of Natural History and the Yale Center for British Art.