Still, Scarsdale reigns as the Über-burb -- for better and for worse. Founded in 1701, it didn't begin attracting urbanites until the New York Central railroad line was electrified around 1910. In the decades after World War II, the town came to represent a particular baby-boom ideal: You could work in the city but live like a country squire amid tree-lined streets, stately homes, very little crime, and schools that siphon students directly to the Ivy League. By the sixties, it was renowned as an enclave dominated by educated upper-middle-class commuters.

But it also came to be used as shorthand for nouveau riche insularity, snobbishness, materialism, provincialism, and conservatism, the Jewish counterpart of the Waspy New Canaan depicted in Rick Moody's The Ice Storm. In the fifties, Guys and Dolls' Sky Masterson sneered about a "Scarsdale Galahad, a breakfast-eating, Brooks Brothers type"; in the nineties, Jonathan Larson (who grew up in White Plains) made it the hometown of Mark the filmmaker and his nagging Jewish mother in Rent. Native daughter Gish Jen lightly lampooned it (as "Scarshill") in her novel Mona in the Promised Land.

The town is notoriously sheltered. Its biggest political strife concerns leaf-blower noise and property zoning; change is so abhorred that plans for downtown commercial development have remained stymied for decades. "People want to keep things here the same, keep it a bulwark of safety and peace," notes the editor of the Scarsdale Inquirer, Linda Leavitt, 52, herself a returnee following a divorce. "You read the police blotter -- all these reports of 'suspicious people.' People seem nervous about outsiders and threats to their security."

Meanwhile, Scarsdale keeps getting ritzier. In 1996, Worth magazine estimated Scarsdale's average household income at $222,200, the highest in Westchester (and more than double the county's average). Houses that cost the previous generation $100,000 are selling for $1.5 million; the median is now around $650,000. In the small downtown, froufrou boutiques are replacing homey and service establishments, and in the high-school parking lot, shiny sport-utility vehicles far outnumber used rattle-heaps. At the annual sidewalk sale, I overheard two separate conversations about hair color.

Whereas 25 years ago doctors and lawyers could afford the nice homes, in recent years it's mostly people from Wall Street or with inherited wealth (or Japanese and Indian businessmen temporarily stationed in New York). This demographic holds less true for the returnees, who want in no matter how much it might stretch the budget. When software designers Paul and Penny Bauersfeld told their parents they wanted to move back, "if anything, our parents were trying to talk us out of it," says Bauersfeld. "They thought it was going to be too expensive."

For the previous generation, Scarsdale represented the upper rung of a climb that in many cases began on Ellis Island and the Lower East Side. This unwittingly created a conundrum for their kids: Though they were being groomed for even further success, where could they go that was "better"?

John McCann, 36, who sells ads for CNBC, first lived on 108th and Amsterdam, then in Tuckahoe; he looked at Chappaqua, Rye, and elsewhere, but, he says, "in terms of house prices, taxes, and everything offered -- all the reasons my parents moved here from Eastchester -- there wasn't a place that could compare." He bought a small house in Scarsdale's less expensive Edgewood neighborhood. A few years later he bought out his parents, and now he sleeps in their former bedroom. ("We made some changes in how it looks," he stresses.) He enjoys being recognized by teachers and store owners, though, he admits, "my wife says she doesn't want to hear anymore what store that was twenty years ago." And at his tenth reunion, she asked him, "What's the big deal? You see these people every day."