In 1996, when congress declared a certain piece of this country "the landscape that defined America," they didn’t mean Yellowstone, Yosemite, or the Grand Canyon. They were talking about New York’s Hudson Valley, where Teddy Roosevelt summered, James Fenimore Cooper penned The Last of the Mohicans, Thomas Cole made his name as a painter, and Washington Irving set his international best sellers. Had Rip Van Winkle overslept a few centuries, he would have found his beloved Catskills relatively unchanged: Bald eagles still soar over tree-lined tributaries (though so do gliders), and sleepy hollows provoke the same shivers that spooked Ichabod Crane one misty autumn night.
Fifty miles north of Manhattan, the Hudson Highlands offer the greatest geological show in the Valley: Storm King Mountain rises suddenly to the west, Breakneck Ridge to the east. The riverfront village of Cold Spring sits in the thick of it all. Drop your bags just a quarter mile from the trailhead at the Pig Hill Inn ($150; pighillinn.com), then take the four-hour, 1,400-vertical-foot Washburn Trail loop around Mount Taurus, aka Bull Hill, for big, panoramic vistas.
Little-known fact: Wurtsboro, New York (pop. 1,234), is home to the oldest glider airport in the country. Hop into a two-man sailplane with a pilot-instructor and catch thermals 5,000 feet above the Shawangunks, keeping an eye out for the New York City skyline ($75 for a 20-minute flight; wurtsboroairport.com). Calm your nerves with a glass at Brimstone Hill Vineyard and Winery (tastings, $2; brimstonewinery.com) before calling it a night at the Catskill Mountain House Bed & Breakfast ($99; catskillmountainhouse.com).
Every October some 50,000 leaf-peepers bum-rush Catskill Park—and with good reason. Dodge the conga lines for a mountain bike ride on Elm Ridge, covered with red oaks, sugar maples, and 15 miles of cleared singletrack (plus ten more slated to open this fall). "It’s true forest, so it’s hard to find a great view," says Nick Bove, founder of Windham Mountain Outfitters. "But that’s why I love fall up here. You get to see the foliage from within" (bike rentals, $35 a day; windhammtoutfitters.com).
This past spring Larry Federman made a major discovery in the RamsHorn-Livingston Sanctuary: two bald eaglets sitting in a tree. According to Federman, who has been leading canoeing tours in the marsh since 2003, the sighting bumped the number of known Hudson Valley nests up to 20. Follow the avian guru on a half-day, out-and-back paddle through the sanctuary to the Hudson River and keep your binocs handy—chances are you’ll see at least one baldie ($20; 518-678-3248).