From its origins as a Connecticut River trading post in 1633, Hartford has become not only the state capital but also the insurance capital of the world, with a slew of historical attractions, a thriving arts and entertainment centre, a revitalized riverfront and beautiful parks and public gardens. It was here that the lovable Huck Finn and Tom Sawyer were born in the imagination of celebrated author Mark Twain and immortalized on paper during the writer's Hartford years. Twain's home and those of fellow literary figures Harriet Beecher Stowe and Noah Webster are open to the public. The Wadsworth Atheneum, the oldest public art museum in the U.S., houses Pilgrim-Century furniture, the Amistad collection and a special treasure hunt system to entice kids to explore the museum's works. If your timing is right (end of June, beginning of July), you'll catch the Elizabeth Park rose gardens in bloom, but fall is also great for brilliant leaf colours, and spring yields colorful gardens and blossoming trees. For a bird's-eye view of the city, visit the observation deck of Travellers Tower, where you might also spot two resident falcons.

The legendary Hamptons, a cluster of wealthy enclaves on Long Island's South Fork, remains a celebrity summer playground, with splashy restaurants and nightclubs galore. But lovely beaches, fishing and kayaking attract off-the-A-list visitors, as well. Old money oozes throughout Southampton, while new wealth reigns in East Hampton. Montauk is a hit with fishermen and surfers. The Long Island Railroad travels the Hamptons in an hour. The Sag Harbor Whaling Museum and Montauk lighthouse are popular stops.

The first time you go to New York, go ahead and be a sight-seer—everyone should visit the Statue of Liberty, the Met, Times Square, etc. But on a return trip, pick a neighbourhood and go deep. You’ll find hole-in-the-wall bars, great delis, quirky shops… exploring the non-touristy side of New York is an incredibly rewarding experience for a traveller.

Artists, farmers, scholars and professionals come together in harmony in beautiful Northampton, where the Connecticut River winds through the wooded hills of the Pioneer Valley. Once home to such diverse notables as U.S. president Calvin Coolidge, abolitionist Sojourner Truth, author Kurt Vonnegut and punk rockers Kim Gordon and Thurston Moore, and current home of the all women's Smith College, the city is famed for its arts scene and liberal values, plus a thriving lesbian community.