If you look north as you cross the Tappan Zee Bridge (I-287) over the Hudson River, you take in what Dutch explorers saw almost 400 years ago. The river here runs nearly three miles wide, carving between mountains and promontories—a glittering path into an emerald land. You will follow the trails of Indians, adventurers, George Washington's Continental Army, and Gilded Age millionaires, while enjoying vistas that inspired the Hudson River school artists more than a century ago. Sharp peaks, deep valleys, woodlands, and farms divide artsy, gentrified communities. Historic sites and many of the grandest mansions in the nation—including FDR's longtime home at Hyde Park—abound.
The drive runs from the town of Nyack, on the Hudson's western bank, northward to Kingston and Rhinebeck, then south along the Hudson to Tarrytown. Highlights include museums, grand estates, West Point, and an aerodrome.
Start in Nyack
Begin in the funky town of Nyack, an old Dutch farming community settled around 1680 that now lures city folks seeking weekend refuges. Trendy boutiques, galleries, antiques shops, and ethnic restaurants give Nyack something of a Greenwich Village feel. Edward Hopper, the 20th-century painter known for Nighthawks and other stark portrayals of loneliness, grew up here. His home, the Edward Hopper House Art Center, contains materials depicting his life and provides exhibit space for local and national artists.
Bear Mountain State Park
From Nyack, head north on U.S. 9W along forest and rolling hills through the town of Stony Point. As the forested mountains rise above the misty Hudson, you reach 5,067-acre (2,051-hectare) Bear Mountain State Park. Take the George W. Perkins Memorial Drive to the top of 1,284-foot (391-meter) Bear Mountain, where you'll find commanding views of the river far below. During the Revolutionary War the Americans commanded two forts here. The park also offers a wildlife center, camping, hiking, golf, boating, and the Bear Mountain Inn, with a restaurant. U.S. 6 and NY 17M lead west to the village of Monroe, and the Museum Village, which re-creates a 19th-century village.
Continue west on NY 17M through farm country to Goshen. This prosperous town is the site of the Goshen Historic Track, tucked just off the main street. The harness-racing track looks like a mini Churchill Downs, with 1890s turrets and wooden bleachers. Few races are held today, but horses and drivers still train here. Nearby is the Harness Racing Museum and Hall of Fame, which tells the story of the sport.
The drive continues northeast on NY 207 past farms, then north on NY 208 to New Paltz. This town's claim to fame is the Huguenot Street National Historic Landmark District, a street boasting seven house museums (six are original) depicting the lifestyle of upper-middle-class French Protestants who settled here in 1677. New Paltz gains its vitality from the students attending the local state university, as well as from the rock climbers who come to test their skills on Shawangunks Ridge. Also known as "the Gunks," these 300-foot (91-meter)-high cliffs rate as one of the nation's most popular rock-climbing areas. Beyond you'll spot the gates to the Mohonk Mountain House, a sprawling, quirky 19th-century resort hotel by Mohonk Lake that looks like an Old World castle-lodge and is a member of Historic Hotels of America.
A few miles beyond Mohonk, County Rd. 6 joins County Rd. 1, bringing you to the river port of Kingston, settled by the Dutch in 1652 and designated New York's first state capital in 1777. Filled with old stone buildings with half-open Dutch doors, the Stockade District forms the heart of Old Kingston. The Visitor Center of the Kingston Urban Cultural Park has information on the area. Also head down to the river and stroll the Rondout, Kingston's 19th-century waterfront district buzzing with cafes, shops, and boat tours. Also here: the Trolley Museum of New York and the Hudson River Maritime Museum.
Take U.S. 9W north and cross the Hudson on the Kingston-Rhinecliff Bridge into the genteel world of the Gilded Age. At the heart of this world stands the village of Rhinebeck, with over 300 sites on the National Register of Historic Places. Check out the Beekman Arms, one of America's oldest continually operating hostelries (1766). Also here is the Old Rhinebeck Aerodrome, where local resident Cole Palen created a World War I-style airdrome to display and fly his collection of vintage aircraft. On summer Saturdays pilots reenact flights from the 1930s; Sundays, it's World War I "battles." In the vicinity are numerous historic mansions, part of the Hudson River National Historic Landmark District, including Clermont State Historic Site, home to seven generations of the influential Livingston family; Montgomery Place, a classical revival estate open seasonally; and Staatsburgh State Historic Site, reputedly one of the settings for novelist Edith Wharton's The House of Mirth.
Soon you enter the village of Hyde Park, where architecture buffs will want to stop at the Vanderbilt Mansion National Historic Site. The 54-room beaux arts palace was built in 1898 by Frederick Vanderbilt, grandson of railroad magnate Cornelius Vanderbilt. Once called "the finest place on the Hudson between New York and Albany," the estate is nothing short of a monument to the wealth that made the Vanderbilts America's richest family in the 19th century. Less grand but perhaps more historic is another Hyde Park estate, the Home of Franklin D. Roosevelt National Historic Site. FDR grew up in this Georgian colonial house, part of the family estate known as Springwood. On display: Roosevelt memorabilia and the presidential library. Nearby sits the Eleanor Roosevelt National Historic Site, known as Val-Kill, where FDR's wife lived in her later years. A final stop in Hyde Park is the Culinary Institute of America, one of the nation's premier cooking schools. You can eat in four different restaurants, but you'll need reservations.
United States Military Academy, West Point
Back on U.S. 9W, continue south through Newburgh, where George Washington and his troops stationed themselves at the close of the Revolutionary War. Continue to NY Route 218, which offers heart-stopping vistas as it twists around Storm King Mountain high above the Hudson. This route carries you through West Point. The best way to see this military icon—a community unto itself—is to take a one-hour bus tour from the Visitor Center.
Exiting the academy to the south, cross the river and go south on NY 9D for a few miles. Follow U.S. 9, NY 9A, and NY 100 to Sleepy Hollow, and Philipsburg Manor, an 18th-century working farm. A shuttle leaves here for Kykuit, the country home of several generations of Rockefellers and the crown jewel of Hudson Valley mansions. Sleepy Hollow Cemetery is the final resting place of writer Washington Irving and other notables. Next door, the Old Dutch Church of Sleepy Hollow was said to be the haunt of a headless Hessian ghost—giving birth to Irving's The Legend of Sleepy Hollow.
End at Tarrytown
Proceed a bit farther south to the site of Lyndhurst. An 1838 Gothic Revival mansion loaded with original furniture and art, it was at one point the home of railroad magnate Jay Gould. Finally, dreamers and literary fans will want to tour Washington Irving's Sunnyside, where the author lived off and on from 1835 until his death in 1859. Costumed guides lead you through this architectural flight of fancy, which Irving once referred to as being as "full of angles and corners as an old cocked hat."
This 210-mile (338-kilometer) drive makes a nice three-day excursion. Summers bring added volume to scenic back roads, so the best times for fewer cars and temperate weather are April through mid-June and September through mid-October. For more information, visit www.vintagehudsonvalley.com, travelhudsonvalley.org, and www.hudsonvalley.org.
—Text by Randall Peffer, adapted from National Geographic's Driving Guides to America: New York