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  • Essex (CT): A walk past white-clapboard houses to the active waterfront on this narrow, unspoiled stretch of the Connecticut River rings all the right bells. You won’t encounter an artificial note or a cookie-cutter franchise to muddy its near-perfect image. Be sure to take a ride on a vintage steam train or Mississippi-style riverboat. 

  • Hanover (NH): It’s the perfect college town: the handsome brick buildings of Dartmouth College, a tidy green, a small but select shopping district, and a scattering of fine restaurants. Come in the fall, and you’ll be tempted to join in a touch football game on the green.

  • The Kennebunks (ME): Chic yet relaxed, this pair of historic shipbuilding towns have long lured summertime visitors with enchanting architecture, first-rate beaches, and the vibrant Dock Square waterfront shopping and dining district. It’s still a bit of a best-kept secret, though, that “The Bunks” stay lively in the off-season, when you may get an even better sense of the community spirit that imbues the town with individuality. 

  • Marblehead (MA): This enclave of the yacht set has major picture-postcard potential, especially in summer, when the harbor fills with boats of all sizes. From downtown, stroll toward the water down the narrow, flower-dotted streets. The first glimpse of blue sea and sky is breathtaking. 

  • Oak Bluffs (Martha’s Vineyard, MA): Stroll down Circuit Avenue in Oak Bluffs with a Mad Martha’s ice-cream cone, and then ride the vintage Flying Horses Carousel. This island harbor town is full of fun for kids and parents. Don’t miss the colorful “gingerbread” cottages behind Circuit Avenue. Oak Bluffs also has great beaches, bike paths, and the Vineyard’s best nightlife.

  • Northampton (MA): “Noho” is the cultural center of the Pioneer Valley, the north-south corridor in central Massachusetts that runs along the Connecticut River. Home to Smith College, handsome Northampton beats out neighboring college towns Amherst and South Hadley by virtue of its diverse restaurants, funky shopping, and top music venues. 

  • Stockbridge (MA): Norman Rockwell famously painted Main Street in this, his adopted hometown in the southern Berkshires. Then, as now, the Red Lion Inn and the other late-19th-century buildings make up the commercial district, with residential areas a beguiling mix of unassuming saltboxes and Gilded Age mansions. The Norman Rockwell Museum gives an excellent overview of the artist, the town where he worked, and the social issues he addressed in his mid-20th-century art. 

  • Woodstock (VT): Woodstock has a stunning village green, a whole range of 19th-century homes, woodland walks leading just out of town, and a settled, old-money air. This is a good place to explore on foot or by bike, or to just sit and watch summer unfold. 

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.