From Manhattan, northern Dutchess County is a 2 1/2-hour drive up the Taconic State Parkway to Route 199 and Red Hook, or via the Saw Mill River Parkway to I-684, then Route 22 to Amenia or Millerton. Amtrak service between New York and Albany stops in Poughkeepsie and Rhinecliff. Metro-North, the commuter train, has two lines to the county: the Harlem Line (its terminus is Dover Plains) and the Hudson Line (which ends at Poughkeepsie). You can also fly into Stewart International Airport, across the Hudson River in Newburgh. However you travel, you'll need a car once you get there.
Beekman Arms 4 Mill St., Rhinebeck; 914/876-7077; doubles from $85. Built in 1766, the Beek is the oldest continuously operating hotel in the country. The inn has 59 rooms spread throughout the main building, the Delamater House (an American Gothic dating to 1844), and newer buildings added to accommodate business meetings. While done in classic American prints, antiques, and reproductions, rooms all come with modern conveniences—cable TV, dataport access, refrigerators, and air-conditioning (though you'll never really need it).
Simmons' Way Village Inn 33 Main St., Millerton; 518/789-6235; doubles from $145. The Carters—Richard, Nancy, and their son, Erich—are the perfect innkeepers: helpful, efficient, and friendly. You'll be sorry to leave the peaceful, nine-room rambling Victorian, especially if you stayed in one of the rooms with private balcony and working fireplace (No. 2 has the best view). In the lobby, the African gray parrot Max keeps guests amused with his thousand-and-one voices.
Troutbeck Leedsville Rd., Amenia; 914/373-9681; doubles from $375. This beautiful 1920's stone Tudor manor house is a conference center during the week. On weekends, it opens its doors—as well as its 600 acres of gardens and nature preserve—to individual guests. The 42 rooms are blessedly frill-free, with Early American fabrics and European-repro furniture. But the real draw is the building itself, all leaded-glass windows, built-in bookshelves, and fireplaces. No children under 12.
Veranda House B&B 82 Montgomery St., Rhinebeck; 914/876-4133; doubles from $90, no credit cards. The four-room inn, awash in flocked floral wallpaper and fabrics, has a great full breakfast. If it's sunny, eat your orange yogurt pancakes on the flagstone terrace; then head out for a bit of shopping: Veranda House is just three blocks from the town center. There's a two-night minimum on weekends.
BEST VALUE Red Hook Inn 31 S. Broadway, Red Hook; 914/758-8445; doubles from $75. The five spacious guest rooms are decorated simply with framed antique prints, large wooden armoires, and dried flowers. The dining room and forest-green bar are packed on weekends (but they quiet down at 10 or so; it is the country, after all).
Poet's Walk Romantic Landscape Park River Rd., Red Hook; 914/473-4440, ext. 229. The popular Hudson River path was frequently trod by Washington Irving and nature poet Fitz-Greene Halleck. A viewing pavilion, with clear sight lines across the river to the Catskills, is a natural spot for contemplating the bigger questions.
Harlem Valley Rail Trail Mechanic St., Amenia; 518/789-9591. So far, the converted railbed trail is only nine miles long, one section beginning in Amenia and one winding through the hills to Copake Falls in Columbia County. But when completed, it'll go for 23 miles. It's a great way to explore the countryside—the path always has people on it, from kids with training wheels to retirees on cruisers. Tip: Trail etiquette requires a "Hello" (or at least a smile) when passing.
Innisfree Garden Tyrrel Rd., Millbrook; 914/677-8000; open Wednesday-Sunday (call for hours). There's something akin to Yeats's "bee-loud glade" in this 200-acre fairyland, a garden and park designed by the former owner, painter Walter Beck. Distinctly Eastern in feel, the plantings in and around the central lake and lotus pond are serenely beautiful.
Mary Flagler Cary Arboretum Rte. 44A, Millbrook; 914/677-5359. Nineteen hundred acres of research and education facilities are also home to the Institute of Ecosystem Studies, and the trails and public gardens are open throughout the year. Visitors can wander around the outdoor perennial beds (where about 1,000 varieties grow), a native wildflower and fern glen, a butterfly garden, forest trails, and the tropical greenhouse.
Start in Red Hook and drive east on Route 199. In no particular order, you'll pass shops, beautiful farms, diners, some run-down barns, lakes full of rushes, ponds full of ducks, leaping deer, small-town main streets, undisturbed forest, and the occasional wild turkey. The road's curves are fun, but be careful: the speed limit dips to 30 in spots.