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From Great Neck to Wading River

With its graceful bays and breathtaking views of Long Island Sound -- not to mention its unbeatable proximity to Gotham -- the North Shore is a spectacular stretch of real estate. It's no wonder the country's newly rich industrialists chose to build their mansions here at the turn of the 20th century.

The towns that line this coast have been inhabited by some of America's wealthiest citizens for decades, and this still holds true. During the Roaring Twenties, the Gold Coast, as it came to be known, was transformed into a playground of the rich, who built sumptuous homes and gardens, threw lavish parties, groomed racehorses, and indulged in, well, just about everything. Barons -- with bold-faced names like Astor, Vanderbilt, and Chrysler -- bought up to 1,000 acres of land and built 100-room mansions modeled on English manor houses and French châteaux.

Yes, this is Great Gatsby country -- and lucky for you, you can still glimpse some of these estates from the Long Island Expressway, and see others up close, through a tour or a house visit. Drive out from Manhattan, past the densely populated, mall- and car-choked sections closest to the city, and pick up Route 25A in exclusive Great Neck -- the inspiration for Fitzgerald's West Egg, by the way. Continuing east, watch as the traffic slowly starts to dissipate, and sit back and take in some of the North Shore's unexpected gems.

Old Westbury House and Gardens, Sands Point Preserve, and Planting Fields/Coe Hall are well worth a visit, with gorgeous gardens and grounds that beg you to linger, while Sagamore Hill -- Theodore Roosevelt's summer home -- makes for an excellent stop. But the North Shore's charms go beyond the mansions: There are also museums, sweeping vistas, hidden gardens, and historic villages that seem to become more charming the farther out you drive onto the island.