93 Best Sights in Long Island, New York

is one of the few former Long Island estates still intact, and today the grounds and 1906 Gold Coast mansion built by financier-sportsman John S. Phipps are open to the public. The mansion showcases the home's original furniture and the family's art and belongings; the beautiful 160-acre property includes formal gardens, fountains, woodlands, and lakes.

Top wines here, like the rich Cabernet Sauvignon, are becoming serious players, but the winery still knows how to have fun. During prime season they offer plenty of picnic tables on the lawn (pack your own lunch), three BBQ stations, a volleyball net, an outdoor bar, and live music on weekends. Try the 2011 Carmenere. For a true taste of the holidays, go for the spice wine, and serve it warm.

A small, old-fashioned tasting room leads out to a wooden deck and lawn—a top spot for watching the sun set over acres of vines and farm fields. Palmer wines regularly impress top critics, especially the "41/72" merlot cuvée. The Sauvignon Blanc and Cabernet Franc are among the most popular vintages here. In-season, look for special events including live music, yoga, food truck, and Friday night firepit with open mike.

The Massoud family tends the vines, makes the wine, and greets visitors in a tasting room that has a great view of the whole wine-making operation; ask, and you might be shown the extensive catwalk system. Paumanok wines, traditionally crafted, consistently receive top marks, and the Chenin Blanc and Rieslings are the most popular.

The working farm on 13 riverfront acres west of Riverhead grows more than 700 varieties of plants, including herbs, heirloom vegetables, beautiful shrubs, and roses. Wander through the trail gardens, visit the eight greenhouses, and (in season) stop by their farmers' market. Garden-related workshops and other events are offered off-season. Artists and photographers are welcome to utilize the gardens for inspiration.

With a tower over the tasting room and an interior courtyard, this winery is an architectural standout and provides a beautiful envoronment for a wine tasting. Unlike the many wineries these days that are augmenting their attraction with music, fun, and games, at Pellegrini it's all about the wine. Coupling old world traditional methods—like growing and harvesting the healthiest and ripest grapes and employing the best winemakers—with new winemaking technology, Pellegrini is known for producing some of the finest wines, including the limited reserve Petite Verdot, Encore, Vintner's Pride Chardonnay, and Finale. Weddings are held here almost every weekend in warm-weather months, so call ahead before visiting, as hours many change.

As the region's largest producer, Pindar can attract visitors three-deep at the bar, with a fun crowd enjoying ample free tastes of approachable wines. Tours are a real education for beginners and experienced hands alike; on November weekends a special tour shows how sparkling wine is made. The Mythology Meritage is a standout, and, on the sweeter side, the Sweet Scarlet and Winter White are easy drinking for wine newbies.

The home of insurance magnate William Robertson Coe from 1910 to 1955, Planting Fields is now a public arboretum with 160 acres of gardens and plant collections and 250 acres of lawns and woodlands. Two greenhouse complexes nurture native plants. Coe Hall, the estate's magnificent Tudor-style manor, is filled with period furnishings and antiques, including windows from the home of Henry VIII's second wife, Anne Boleyn. Guided tours of the house are available.

The house where abstract expressionist Jackson Pollock painted his masterpieces is now a museum and study center. You can see the paint-splattered floor of his studio, plus exhibits on Pollock and his wife and fellow artist, Lee Krasner. Call for a schedule of art exhibits, lectures, workshops, and guided tours.

Housed in an 1892 freight station, the museum exhibits a Reading Railroad track car, a 1907 snowplow, and a 1925 Long Island Rail Road caboose. Admission includes a guided tour and admission and tour of the Riverhead site, where most of the train cars reside and much of the restoration work takes place. If you want to make a day of it, for an extra fee, ride the nearby LIRR for a tour of both sites.

More than a home for old railroad cars, this museum, with another location in Greenport, outlines the history and development of Long Island railroads. Created in 1990, the museum and its curators preserve and restore cars and artifacts that contributed to the island's communities and industries. A World's Fair miniture train ride operates spring through autumn, weather permitting. Admission includes a guided tour of both sites. If you want to make a day of it, for an extra fee ride the nearby LIRR for transportation between the sites.

The winery is a boutique producer of high-end merlot, but the lavish Spanish mission–style winery, built with wrought iron and stone, is worth a visit on its own. The best-selling wines here are the First Label Sauvignon Blanc 2013 and La Fontana 2010 Bordeux-style blend. Live music takes place on Sunday.

Three generations of the Townsend family, renowned merchants and ship traders, lived in this colonial saltbox structure dating from the American Revolution. Sally Townsend was responsible for alerting her father to the fact that a certain Benedict Arnold was going to betray his country. Many of the original family furnishings are in the house, and there are rotating exhibits of Civil War memorabilia and holiday decorations. The house-museum reveals much about Oyster Bay from the time of the Revolution through the town's affluent Victorian period.

One of the oldest stock-car racing tracks in the country and the only NASCAR track in the New York Metropolitan area, Riverhead Raceway also hosts monster truck rallies, school bus demolition derbies, and hosts special events including amusement rides and fireworks. Bring ear plugs if you don't like loud noises.

Built in 1767, this Georgian Colonial manor is one of Long Island's finest and best-preserved homes of the era. Home to Josiah Martin, a wealthy West Indian planter and British Loyalist during the Revolutionary War, it was given to the Town of Hempstead in 1948, and is presently on the National Register of Historic Places and part of the New York State Revolutionary War Heritage Trail. The home is now a museum with period furnishings and educational and cultural programs for all ages.

Four severe blazes in town in the 1800s led to the establishment of the first volunteer fire department in New York State. The museum, housed in an 1833 building that served as fire-company quarters as well as town hall, displays an 1890 hand-pulled hose cart, a 1920s fire chief's vehicle, model fire trucks, and other old firefighting equipment.

Noted 19th-century architect Minard Lafever designed this striking 1845 Greek Revival mansion for shipowner Benjamin Huntting and his family. Museum displays include scrimshaw pieces, a boat collection, period furnishings, and model ships. Special exhibits take place in the summer, events include the Harborfest Party, and tours of a whaling captain's house are offered.

Known for a time as the "summer White House," this 23-room Victorian was President Teddy Roosevelt's cherished family retreat from 1885 until his death in 1919. In addition to the original furnishings and some personal effects, the house contains animal heads and skins from Roosevelt's many hunting expeditions. The servants' quarters offer a behind-the-scenes look at life here.

Docents in period dress are on hand to take you on a tour of this historically important home dating back to 1697. The manor served as a military headquarters for the British Army during the Revolutionary War, and George Washington slept here after the war, in 1790. Today the 150-acre estate holds a substantial collection of antiques and historical exhibits depicting its early days. Special events including seasonal festivals, holiday celebrations, and art, antiques, and car shows are held here throughout the year.

Overlooking Long Island Sound, this 216-acre preserve, once part of a Gold Coast estate, occupies the tip of the Port Washington Peninsula. The grounds include natural and landscaped areas, with forests, meadows, freshwater ponds, and shore cliffs. Also here are three castlelike mansions. The 1904 Castlegould, the visitor center, houses changing exhibits on natural history. Falaise is a Normandy-style manor house built for Harry F. Guggenheim in 1923; the home is notable for its medieval and Renaissance style and artwork. The Tudor-style Hempstead House, used for various exhibits, overlooks the harbor. Tours through Falaise and nature walks are available.

This tiny village 4 mi north of Roslyn is filled with turn-of-the-20th-century homes, most lovingly restored to their original grandeur. Shops and restaurants in the village make it a pleasant destination for an afternoon visit.

At the Sea Cliff Village Museum, displays of documents and photos trace the history of Sea Cliff. A scale model of a village Victorian house is also on exhibit.

The second house built in Montauk, this 1700s farmhouse holds a collection of early photos and artifacts that depict the era when it was surrounded by pastures, sheep, and cattle. Now enveloped by gorgeous lawns, rose gardens, and hydrangeas, it is the site of daily tours and two well-attended summer crafts fairs in July and August.

The museum encompasses seven historic structures, including an 1843 whaling captain's home (awarded a unique design designation on the National Register of Historic Place), a country store, an old-fashioned apothecary, a pre–Revolutionary War barn, and a blacksmith shop. Montauk and Shinnecock tribal artifacts are also on display. Art exhibitions, music recitals, classes, and year-round special events are held, including summer cocktail parties (and an occasional "yappy hour" for the pups), Harvest Day in September, a Latin Fiesta in October, and the Hearthside Cheer celebration in December.

The complex, run by the Southold Historical Society, encompasses a dozen buildings, several of which are listed on the New York State Register of Historic Places. Arranged as a quaint village, they include the home of the society's founder, Ann Currie-Bell, with antique dolls and toys, costume collections, and period rooms; the Thomas Moore House, a mid-18th-century carriage house and blacksmith shop; the circa 1821 Old Bay View School, which now looks as it did in 1914; and a buttery and icehouse.

At this 96-acre water park you can ride an inner tube down the 1,300-foot-long Lazy River, passing waterfalls, geysers, and wave pools, or go for something more exhilarating (or scary). Attractions include Monsoon Lagoon, Mammoth River Ride, Kiddie Cove, and the new Bootleggers Run and Battle of Mutiny Bay water roller coasters. The park has three pools, a beach area, four restaurants, and the Parrots of the Carribean show.

William K. Vanderbilt's 24-room Moroccan-style mansion, called Eagle's Nest, sits on 43 acres and houses collections that Vanderbilt acquired as he traveled throughout the world. Summer brings various theatrical performances to the mansion's courtyard. The adjacent planetarium is one of the best equipped in the nation, with a 60-foot domed Sky Theater. Sky and laser shows are held regularly.

Down the road from Sagamore Hill, Teddy Roosevelt's family home, is this 12-acre bird sanctuary—the perfect legacy of the environmentally active president. More than 125 species of birds live here. Roosevelt is buried in a cemetery on the grounds.

You can see a blacksmith at work using traditional, antique tools at this historic shop behind the old schoolhouse in the center of town, and the artisan on site is enthusiastic about answering questions about his craft and the history of blacksmithing in Greenport. Housed in an old East Marion onion shack, the building is a replica of the original, destroyed by a nor'easter in 1992. You can purchase small, handmade items made here including wall hooks, and the proceeds help fund the site, which is part of the East End Seaport Museum.

This was the boyhood home of Walt Whitman, one of America's greatest poets. A typical example of native Long Island craftsmanship of the time, the snug house, built by the poet's father circa 1819, has survived virtually intact since the Whitmans left it in 1823. Whitman portraits, letters, and manuscripts are on display. The home is off Route 110, across from Walt Whitman Mall.