DAY 1

Taking Route 9 out of New York City, I stop in Tarrytown at the home of writer Washington Irving (“Rip Van Winkle,” “The Legend of Sleepy Hollow”). Guides in period costume offer tours of Sunnyside (914-591-8763; 89 West Sunnyside Lane; adults, $9; children ages 5 to 17, $5), the quaint cottage where the well-traveled author spent his final days. A quarter mile north, I also pop in to see Lyndhurst (914-631-4481; 635 South Broadway; adults, $10; children ages 13 to 18, $4), the grand Gothic revival mansion of Wall Street tycoon Jay Gould, who traveled by yacht from his waterfront property to New York City. Highlights of the tour include Gould’s Renaissance-art collection and the fine stained-glass windows.

Stop in Tarrytown for lunch: a Portuguese feast at Caravela (914-631-1863; 53 North Broadway). Grilled octopus melts in the mouth, just as it should, and the codfish croquettes are rich, yet fluffy. Heading north up 9, let’s keep Kykuit, John D. Rockefeller’s expansive family home, for another trip and move on to Croton Gorge Park (914-827-9568; Route 129, Cortland), a favorite local picnic spot. The park sits at the base of the Croton Dam, built in 1842 to hold most of New York City’s drinking water.

Just past Peekskill, take Route 9D, which runs along the river. Soon you’ll be on a long and winding road, beside granite cliffs. With a bit of imagination, this could be the Italian Alps. The tricky part ends at Bear Mountain Bridge, which crosses the Hudson at the place where American Revolutionary forces blocked the path of the British fleet with a giant iron chain. From here it’s only a half-hour drive to Cold Spring. You can putter in and out of the knickknack shops of a Main Street that runs steeply toward the river–it really should be turned into a giant skateboarding park–and take stock of the Lower Hudson’s east side over farfalle al limone ($14) and a glass of Cabernet at Cathryn’s Tuscan Grill (845-265-5582; 91 Main Street). Cold Spring has a number of B&Bs, but the Courtyard by Marriott (845-897-2400; 17 Westage Drive; $149), a few miles north in Fishkill, puts you closer to Beacon, the next day’s first destination.

DAY 2

“This place is changing overnight,” says the teenager in the Chthonic Clash Coffeehouse (845-831-0359; 418 Main Street) as he fixes me a latte. “Some locals don’t like it, but I say the quicker the better.” Named after Mount Beacon, where colonists lit fires to warn of British troops during the Revolutionary War, the town of Beacon has been reborn, thanks to the opening last year of Dia:Beacon (845-440-0100; admission, $10; kids under 12, free), one of the most impressive art galleries in the country. Inhabiting a sprawling 1929 Nabisco factory, the airy 240,000-square-foot space (much of it lit by skylights) is perfect for viewing large art installations. The museum is home to pieces by 22 artists, including Andy Warhol, whose 1978 “Shadows” is a single work on 72 canvases, and Richard Serra, represented by seven monumental sculptures.

You do a lot of walking at Dia, and by the end you’ll be hungry. Head into town for a taste of the old Beacon–bacon and eggs at the wonderfully gaudy Yankee Clipper Diner (845-440-0021; 397 Main Street; lunch special, $6.95), a recently renovated downtown institution. After browsing the galleries and antiques shops that are contributing to the town’s renaissance, stop for an excellent slice of apple pie at the Upper Crust Cafe and Bakery (845-838-2890; 472 Main Street; pie slice, $3.50).

Up next is Hyde Park (845-486-7770; tour, $14). The town is dominated by the 290-acre National Historic Site built around Franklin Delano Roosevelt’s family home and the separate house built for Eleanor Roosevelt a few miles east of Route 9. FDR’s father bought the family home, Springwood, in 1867. Visitors can view the house, FDR’s grave site and the Franklin D. Roosevelt Library and Museum, which includes some 44,000 books along with his White House desk and chair. Nearby is Wilderstein, the majestic home of FDR’s cousin Margaret (Daisy) Suckley (845-876-4818; admission, $8; kids under 12, free), who served as one of the president’s most cherished confidants during the last years of his life.

The late-afternoon light is fading slightly as I drive out of the Roosevelt site, so I put my foot to the floor. There’s a piece of Hudson Valley history that I really want to catch–the ostentatious estate of Frederick William Vanderbilt, also in Hyde Park. Built in 1899, the 54-room Vanderbilt Mansion (845-229-9115; admission, $8; kids under 16, free) was meant to evoke European nobility, and the approach certainly feels as if you’ve entered a royal estate. I’m too late for the house tour, but the grounds are lovely. As the sun begins to set over the western banks of the Hudson, the light casts an orange glow all around.

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 (845-876-7080; $95 to $190), a favorite resting place and watering hole for the weary traveler since 1766. The smell of cooking food and a roaring open fire greets you on arrival.

DAY 3

It’s time to cross the river. The Kingston-Rhinecliff Bridge offers clear views both north and south. 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 cafe and deli called Ann Marie’s (845-246-5542; 216 Main Street; specials, $10). But Saugerties’s most extraordinary attraction, Opus 40 (845-246-3400; adults, $6; kids, $3), 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 6-1/2-acre composition of bluestone ramps, terraces, pools and fountains, with a nine-ton monolith as its centerpiece.

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, cut inland on Route 32. You’re heading for 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 (845-255-1000; 1000 Mountain Rest Road) 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 4

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. Turn right off Route 9 just south of Marlboro and head up a steep hill to Benmarl Winery (845-236-4265; 156 Highland Avenue; tour and tasting, $6), site of America’s oldest vineyard. Kids are allowed on the tour–but no sipping.

Leaving Benmarl, 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 cafes and restaurants. My choice: Cafe Pitti (845-565-1444; 40 Front Street; lunch, $12), a brick-oven pizza joint with outdoor seating and a fine view of Dia:Beacon across the river. An espresso and some raspberry gelato will make the afternoon even more enjoyable and prepare you for the final drive back into New York City.

Make quick time through West Point, hop onto 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.