After so much local history, a motel really won't cut it. Nearby Rhinebeck, a sophisticated town in its own right, is home to the Beekman Arms, a favorite resting place and watering hole for the weary traveler since 1766. The smell of cooking food and a roaring open fire greet you on arrival.

Day three: Rhinebeck to New Paltz

It's time to cross the river. The Kingston-Rhinecliff Bridge offers clear views both north and souththis far upstream, the river is still over half a mile wide.

Saugerties is another of those cute antiquing towns that seem to pop up every 30 miles along this part of the valley. It also has an excellent little café and deli called Ann Marie's. But Saugerties' most extraordinary attraction, Opus 40, is a few miles outside the town limits, in the foothills of the Catskills. Harvey Fite, a devotee of Mayan architecture, spent 37 years working with hand-powered tools to create a six-and-a-half-acre composition of bluestone ramps, terraces, pools, and fountains, with a nine-ton monolith as its centerpiece. He died in 1976, but the sculpture and a museum dedicated to his work are open from Memorial Day to Columbus Day.

The road down from Opus 40 is narrow and winding, so it comes as some relief to get back on 9W, on the western side of the Hudson. At Kingston, I cut inland on Route 32. I'm headed to New Paltz and one of the region's most impressive landmarks. A 251-room Victorian castle on Lake Mohonk in the Shawangunk Mountains, the Mohonk Mountain House was a getaway destination for Teddy Roosevelt and Andrew Carnegie, among others. Today it's an exclusive retreat far beyond my budget. But you can buy a day pass to the grounds for $15 ($11 for kids) and spend the afternoon wandering.

Day four: New Paltz to New York

It takes about 25 minutes to get back to 9W from New Paltz, but from that point on, the road is right by the river. This part of the valley is wine country - at least six vineyards lie between New Paltz and Newburgh, and most offer tours and tastings. I turn right off Route 9 just south of Marlboro and head up a steep hill to Benmarl Winery, site of America's oldest vineyard. A rugged driveway leads to the main house, also the home of owner Mark Miller, who in the '50s and '60s was an illustrator for romance magazines and novels. Miller offers a lively narrative as he guides you through the cellars and a gallery devoted to his former profession. He might even join in a tasting of his trademark Chardonnay and Zinfandel.

Leaving Benmarl, I drive into Newburgh, toward the newly renovated waterfront. Newburgh Landing is part of a $1.8 million state-funded scheme to tidy up the Hudson River. It's home to a number of cool cafés and restaurants.

I choose Café Pitti, a brick-oven pizza joint with outdoor seating and a fine view of Dia:Beacon across the river. An espresso and some raspberry gelato make the afternoon even more enjoyable and prepare me nicely for the final drive back into New York City.

I make quick time through West Point, hop on to the Palisades Parkway, and zip back down to the George Washington Bridge and New York City, stopping just once more to marvel at the tall, sheer vertical drop of the ancient Palisades cliffs that tower over the Hudson below.

Finding your way

From JFK airport, head north on the Van Wyck Expressway to the Bronx-Whitestone Bridge. After crossing, take 678 north to the Cross Bronx Expressway west; exit at Route 9 north.