Rye

The 411: Many call this, the county’s smallest city—approximately 15,000 residents live within its six square miles—its loveliest. And with good reason. This exclusive, picture-perfect community boasts an expansive Long Island Sound beachfront, excellent schools, and a quaint New England-like downtown shopping district complete with town square and dotted with high-end fashion boutiques, gift galleries, and its very own “Restaurant Row” of both fine-dining establishments and family eateries. Very much an old-fashioned small town in feel, Rye attracts plenty of Lily P-clad preppies with deep pockets as well as other upper-middle class families with its traditional, family-oriented ambiance. Its immaculately maintained homes—some of the region’s most expensive—include everything from quaint Victorians and refurbished Cape Cods with charming white picket fences to historic, old-money estates tucked behind gates, many with spectacular water views. Rye is also home to the famed art deco Rye Playland amusement park, and its old-fashioned boardwalk, and the exclusive Rye Country Day School, alma mater of Barbara Bush. And while it has more than its fair share of private golf, yacht, and beach clubs, the city’s own public Oakland Beach and Rye Golf Club, the latter featuring an 18-hole course, swimming pool, and historic castle for fine dining, are equal to them all—and at much more pleasing price points.

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