99 Best Sights in Hudson Valley, New York

Born in Kinderhook, Martin Van Buren (1782–1862)—the eighth president of the United States—decided to retire to this estate, which he purchased during his presidency and called Lindenwald. Built in the Federal style in 1797, the house took on Gothic and Italianate features following a revamp in the mid-1800s. The graceful building can only be visited as part of a guided tour.

At this 130-acre winery and vineyard you may savor a chardonnay or cabernet franc against a backdrop of spectacular views. An upstairs loft is open on weekends and offers seasonal art exhibits with regional artists and a selection of the vineyard's reds and whites.

Formed from Margaret Lewis Norrie State Park and Ogden Mills and Ruth Livingston Mills Memorial State Park, the park encompasses 1,200 scenic acres along the Hudson River, about 5 miles south of Rhinebeck. The grounds include close to 9 miles of hiking, biking, and horseback-riding trails; a marina; nature center; public golf course; and the Staatsburg State Historic Site. Camping is an option; there are tent sites and 10 cabins available for rent between May and October. Atlantic Kayak offers short kayaking tours on the Hudson. Eagles can sometimes be spotted from the nature center.

The 8,000-acre preserve has more than 30 miles of historic carriage roads and trails, and more than 1,000 rock climbing routes. The Preserve's Visitor Center, on U.S. 44/Route 55 in Gardiner, is free to the public and includes an orientation theater, children's forest, and nature trails. You can also enter through the West Trapps and Coxing Trailheads in Gardiner, and the Spring Farm Trailhead in High Falls. Visitors enjoy spectacular mountain views as they hike, run, bike, rock climb, ride horses, cross-country ski, and snowshoe.

This 23-room mansion, once the Livingston family estate, sits on 434 acres along the Hudson River north of Rhinebeck. Built in the Federal style, the mansion was remodeled in the mid-19th century by noted American architect Andrew Jackson Davis, who applied a classical revival style. The well-maintained house is closed for restoration, but the grounds alone are worth seeing; they encompass orchards, flower gardens, and ancient trees, and offer plenty of picnic-perfect spots.

The county park, once a gentleman's farm, was named after a Lenape word meaning "by the swamp," because of its location near what is now part of the New York City watershed. A lively seasonal roster of special events is offered, including hayrides and demonstrations of blacksmithing, maple sugaring, and sheep shearing. Farm animals—sheep, chickens, pigs, goats, cows, horses—are permanent residents.

The stunning 61-acre park, known as Hook Mountain to locals, includes a main trail that stretches alongside the Hudson River and attracts bicyclists, dog walkers, stroller-pushers, and runners. Bird-watchers look for hawks, and area residents come with their lawn chairs and Sunday papers. Bring lunch and enjoy it at a waterfront picnic table, or visit in the colder months and cross-country ski on the trails. Parking is free daily from November through March, and on weekdays from April to mid-June and Labor Day to October.

The graves of many of Nyack's artists and writers, including Edward Hopper, Carson McCullers, and Helen Hayes, are in this cemetery.

The church was established in 1659, and a small wooden building was erected in 1661. It was burned down in 1663, during the Second Esopus War. Today's church (the third at the site) went up in 1852 and features an 1891 window made by the Tiffany Studios. George Clinton (first governor of New York and vice president under Thomas Jefferson) and a number of Revolutionary War soldiers are buried in the graveyard. Guided tours of the cemetery, sanctuary, and museum are offered by appointment.

Built in 1685, the oldest church in New York State is surrounded by a 3 acre burial ground that's mentioned in The Legend of Sleepy Hollow. Made of stone and hand-hewn lumber, the church is in a style typical of the northern Netherlands.

The late Harvey Fite put 37 years into the making of this 6-acre outdoor sculpture, created in the rock bed of an abandoned bluestone quarry. The architectural creation is an assemblage of curving bluestone walkways, swirling terraces, and finely fitted ramps around pools, trees, and fountains. The Quarryman's Museum contains 19th-century tools.

On the bank of the Pocantico River sits this 18th-century farm and provisioning plant owned by Frederick Philipse III, whose Dutch family owned most of the land in the region. Guides in period costume conduct tours of the Dutch stone house filled with 17th- and 18th-century antiques. The museum focuses, however, on the lives and stories of the 23 enslaved Africans who lived here and on slavery in the colonial north. Check out the water-powered gristmill, 18th-century New World Dutch barn, slave garden, and reconstructed tenant house.

Local historical memorabilia and changing exhibits fill this former 19th-century schoolhouse, once attended by children of West Point Foundry workers. A permanent installation and video chronicle the history of the foundry. Paintings, drawings, photographs, and other objects and artifacts round out the museum's collection.

Noted architect Frank Gehry designed Bard's extraordinary Richard B. Fisher Center for the Performing Arts. Brushed-stainless-steel panels, draped like massive ribbons over the roof and sides of the 108,000-square-foot performing-arts center, reflect the light and colors of the sky as well as the hilly surroundings. Tours are given Monday through Friday at 2 most of the year. Call ahead to make sure the theater is open and tours are available.

At the Samuel Dorsky Museum of Art, 19th- and 20th-century photographs and American and European paintings, along with a core collection of works on paper, are focal points.

You can learn about the daily life of the Shakers from one of the largest collections focusing on their culture. The extensive array of clothing and household textiles on exhibit is a highlight. The series of red barns also displays furniture, tools, machinery, and decorative objects from all of the major Shaker communities.

These open meadows and broken woods shelter kildeers, Northern harrier hawks, several types of flycatchers, a few warblers, woodpeckers, eastern kingbirds, and bluebirds. In spring, listen for the evening mating rituals of American woodcocks. In fall, watch for the occasional peregrine falcon—a few breeding pairs nest in the nearby cliffs. In spring through late summer, visitors can see bobolinks and Eastern meadowlarks nesting.

Surrounding the Old Dutch Church is the famous Sleepy Hollow Cemetery. It was featured in The Legend of Sleepy Hollow as the site of the Headless Horseman's hauntings; some of the book's characters come from names on the gravestones. The cemetery is open daily 8:30–4:30.

Great views of the Hudson River and the Tappan Zee Bridge can be seen from this 65-foot-tall all-metal beacon built in 1883.

You can walk the carriage roads and trails that vein this woodsy, 20-acre landscape. It is the only surviving example of a landscape design by A.J. Downing, the 19th-century tastemaker. Downing had designed the landscape in 1850 for the country estate of Matthew Vassar, the founder of Vassar College. A trail guide is available in the kiosk at the site.

The college, which long has attracted arts students, presents the community with a host of cultural offerings on its 216-acre campus.

This is the only Revolutionary War battleground in Rockland County. A museum with exhibits and a slide show describes the battle, and reenactments in period costume are common. It is also the home of the oldest lighthouse on the Hudson River, built in 1826. Lighthouse tours are offered the first and third Saturday of the month, from April to October.

A guide in period costume escorts you through the 1830s home of Washington Irving, whose writings include classics like The Legend of Sleepy Hollow and Rip Van Winkle. The eclectic building, one of the nation's earliest examples of romantic architecture, includes stepped gables that recall Dutch architecture and a curved roof modeled after that of a Spanish monastery. Sunnyside was often called America's Home, because it appeared in many landscape illustrations of the period. Irving's book-lined study is a highlight.

Bird-watchers search the skies for migratory birds such as great blue herons and American avocets at the 500-acre Piermont Marsh, part of Hudson River National Estuarine Research Reserve, itself part of Tallman Mountain State Park. The park is open daily from dawn to dusk, and features a running track, tennis courts, playing field, cross country skiing, walking and hiking trails, and picnic areas.

Greek Revival architecture finds expression in this 1833 chapel atop a bluff facing the Hudson River. Passing sailors have long taken pleasure in the landmark, originally built to support the spiritual lives of West Point Foundry workers. Initially a Catholic church, the nondenominational chapel now hosts ecumenical services, weddings, and other events. The chapel has no set open hours, but the facade is worth a look, and the columned porch is a great place for river gazing.

You may feel the urge to pick up a paintbrush as you take in the Catskill Mountain views from the front porch of the yellow-brick Federal house of the Thomas Cole National Historic Site. Well, at least you can understand what inspired Thomas Cole (1801–48), the painter credited with starting the Hudson River School of Art. Cole came to know the 1815 house, called Cedar Grove, when he set up a studio in an outbuilding he rented on the property; he settled down here after marrying a niece of the owner. James Fenimore Cooper and Asher B. Durand are among the 19th-century luminaries who visited Cedar Grove, 13 miles north of Saugerties.

Wallabies, chinchillas, emus, otters, parrots, snakes, and lemurs are among the more than 100 exotic and indigenous small mammals and birds that reside at this zoo on the grounds of the Millbrook School. Students, along with full-time and consulting staff, run the zoo and care for the animals as part of their curriculum at the college-preparatory school; their enthusiasm for their charges is infectious.

The museum stands on the site of the eastern terminal of the Ulster & Delaware Railroad, which ran from Kingston through the Catskills and was affectionately known as the Up & Down Railroad. Trolley cars dating from 1907 are on display; trolley tours of historic Kingston leave from the museum.

New York's first constitution was drafted on this site in 1777, in an earlier building. Then its first chief justice, John Jay, was sworn in in that courthouse. Shortly thereafter, in the same year, the British burned down Kingston; the current courthouse was built in 1818. Sojourner Truth was freed in 1826, and she immediately—and successfully—sued, in this courthouse, to have her son freed from slavery in Alabama. The courthouse is open to the public while court is in session between 8:30 and 4:30 on weekdays. No photography is allowed.

Livestock, local crafts, baking and preserves competitions, pig races, and amusement rides constitute a genuine old-fashioned county fair. Held in late July/early August, it runs Tuesday through Sunday.