Grab bagels to-go and hop in your car for a full day exploring the historic Hudson Valley. Drive US 9 north as it hugs the eastern shore of Hudson River on its way to a serene landscape of mountains, forests, and farms. Enjoy the scenery on your way to Hyde Park, about three hours by car (a bit quicker, though less scenic, if you take the NY State Thruway and exit for US 9 at Poughkeepsie).
Hyde Park is the historic home of at least two familiar millionaire families—the Roosevelts and the Vanderbilts. Tour The Franklin D. Roosevelt Home, Presidential Library & Museum—a massive home and museum interpreting the lives of Franklin and his wife Eleanor. Open year round, the site is especially charming when decorated for the winter holidays. Don't miss the Rose Garden when in bloom.
Fast forward a few decades and jet to the Eveready Diner for your fill of burgers, malts, and nostalgia. Its cozy vinyl booths set off the stark light of neon signs. The menu is pages long, offering just about any diner fare you can imagine.
The Vanderbilt Mansion lies just north of town and is a winding estate with imposing white-columned porch and elaborate, formal gardens. The grounds are large enough for a vigorous hike on its old carriage trails. Catch the sunset from one of its many scenic overlooks.
One last stop, the town of Rhinebeck, fifteen minutes north, is worth the trip. Great restaurants, trendy boutiques, and local arts and craft shops line the historic main street. Dinner at the Beekman Arms, which claims to be the oldest inn in America, is a warm and romantic treat. The New York Times lauds a newer establishment, Terrapin, for its flavorful organic cuisine. For something less pricy, try dinner at Bread Alone Bakery--and don't forget to grab a loaf of their artisan bread to bring home.