Extreme
Don’t let Mount Washington’s modest altitude (6,288 feet) fool you. New Hampshire’s signature summit is home to some of the world’s worst weather: hurricane-force winds, 40-below-zero temperatures, and occasional snow even in summer. The 4,250-foot elevation gain over the 4.2-mile Tuckerman Ravine Trail (watch for moose) will make you beg for Sandy Pittman’s short-roping Sherpa. But the vistas of the granite Presidential Range and beyond are worth every step (603-466-3347; nhparks.state.nh.us; trips take one long or two short days).
Challenging
Indians named Mount Marcy’s 5,344-foot summit—the highest of the Adirondacks’ 46 peaks—Tahawus, or “cloud splitter.” That’s spot-on. The final section of the rugged Van Hoevenberg Trail, which gains 3,166 feet over 7.4 miles, brings you above treeline, and sometimes above the cumulus and cirrus. Up there, ravens circle above and Lake Champlain and the Green Mountains loom far, far below. Unless you’re in Herculean shape (or you’re Pittman’s Sherpa), pack for an overnight (518-327-3000; northnet. org/adirondackvic; one and a half to two days).
Moderate
The trek up to Overlook Mountain’s 3,140-foot Catskills summit comes with a bonus: a reminder, in this sad-sack economy, that things could be worse. Two thirds of the way up the 1,400-foot climb, you’ll encounter the remains of the Overlook Mountain House, a grand hotel that was under construction but never completed after the stock market collapsed in 1929. The 2.4-mile Overlook Trail tops out above the Indian Head Wilderness, a scenic span stretching from the Hudson Valley to the New England foothills (845-256-3000; catskillcenter.org/towers/ olooktrail.html; four to six hours).
Easy
You can reach Bear Mountain’s 1,306-foot summit via the Appalachian Trail in just two hours, then extend the outing, if you like, by making a full-day loop on the well-marked trail network. The views explain the Hudson River School painters’ rheumy-eyed devotion: On a clear day atop the summit’s Perkins Memorial Observatory, you can see the bald heads of Dunderberg and Timp, the majestic river’s big dogleg right, and the setting sun twinkling off the skyscrapers in Manhattan (845-786-2701; roughly two hours).