Long Island’s storied North Shore, nicknamed the Gold Coast, is famous for luxurious estates and gorgeous gardens, many of which were built around the Gilded Age of the 1920s. The era of excess was immortalized in F. Scott Fitzgerald’s The Great Gatsby, which chronicles the exploits of New York’s upper crust during the 1920s. Between 1890 and 1930, more than 1,000 opulent estates were built on the North Shore. Less than a third remain, but many of them are open to the public. Take the LIRR to Port Washington, Oyster Bay, and Port Jefferson to easily access eight stunning Long Island estates for a Gilded Age experience. Note that some locations require a short walk, bike ride (bring yours on the train), or rideshare from the station.
1. Sands Point Preserve, Port Washington
Once the extravagant home of the Guggenheim family, who bought the estate from financier Howard Gould in 1917, Sands Point Preserve is now 216 acres of outdoor features: six hiking trails, gardens, the Great Lawn, a beach on the Long Island Sound, and a castle themed playground. The preserve is also home to four dramatic mansions.
Hempstead House, the summer home of Daniel Guggenheim and his wife, Florence, features a fully restored Wurlitzer Opus 445 Theater Organ, whose massive pipes reverberate through the floors. Castle Gould, the original home of Jay Gould and his wife, Katherine Clemmons, now serves as a visitor center and Great Hall, where fitness classes and nature programs are held.
Falaise, where Daniel’s son Harry and his wife, Alicia Patterson, the founder of Newsday, lived in the 1920s, is teeming with antiques, mostly from the 16th and 17th centuries. Mille Fleur, a smaller waterside home, became Florence’s residence after Daniel died in 1930.
7 minutes by car or 17 minutes by bicycle from Port Washington
2. Vanderbilt Museum and Planetarium, Centerport
This lavish estate belonged to William K. Vanderbilt, who collected thousands of marine specimens and originally opened a museum on the grounds in 1922. Today the massive estate houses three historic museum buildings with more than 40,000 objects, including marine specimens, ethnographic artifacts, and a 32-foot whale shark. A planetarium screens laser light shows, and an observatory is open to the public on Friday nights. The Eagle’s Nest mansion, built between 1910 and 1936, is open to the public for tours. The Vanderbilt Museum hosts events including ballet and theater performances, concerts, and family activities.
7 minutes by car or 18 minutes by bicycle from Greenlawn
3. Planting Fields, Oyster Bay
This sprawling 409-acre estate was once the home of shipping insurance mogul William Robertson Coe and his wife, Mai Rogers Coe, heiress to Standard Oil. The two built Coe Hall between 1918 and 1921 to resemble an English manor. They employed the Olmsted Brothers—sons of Frederick Law Olmsted, who designed Central Park—to landscape the grounds, which has several greenhouses, rambling lawns, formal gardens, forest trails, and impressive plant collections filled with magnolias, roses, and dahlias. Visitors can come for guided tours of Coe Hall and to enjoy the Planting Fields Arboretum. Planting Fields also hosts concerts, art exhibits, yoga classes, and art workshops.
4 minutes by car or 12 minutes by bicycle from Oyster Bay
4. Sagamore Hill National Historic Site, Oyster Bay
Known as the Summer White House during Theodore Roosevelt’s presidency, the 83-acre Sagamore Hill played host to numerous foreign dignitaries and politicians of the time. It was also the Roosevelts’ home from 1885 until the president’s death there in 1919. Today it’s managed by the National Park Service, and visitors can tour Roosevelt’s house with an advance reservation, plus stroll along nature trails that traverse woodlands, salt marshes, open fields, and Cold Spring Harbor Beach. Keep your eyes peeled for bald eagles and other wildlife.
8 minutes by car or 19 minutes by bicycle from Oyster Bay
5. Old Westbury Gardens, Westbury
Two hundred acres of formal gardens surround a Charles II English-style mansion, Westbury House, completed in 1906 at Old Westbury Gardens. The home of businessman and heir John S. Phipps and his family, Westbury House is furnished with English antiques and artwork collected over the 50-plus years the family resided there.
Now, visitors can take a self-guided tour of the home and gardens, which include a rose garden, walled garden, and lilac walk, and then have lunch at the charming Café in the Woods. Programming includes nature lectures, outdoor concerts and festivals, gardening classes, yoga and Tai Chi in the garden, and a storytime stroll in the gardens for children.
6 minutes by car or 13 minutes by bicycle from Westbury
6. Caumsett State Park Historic Preserve, Lloyd Harbor
A New York State Historic Park Preserve, Caumsett was previously the estate of department store heir Marshall Field III and his wife, Evelyn. Built between 1922 and 1927, the nearly 2,000-acre estate had numerous buildings and meticulous landscaping designed by the Olmsted Brothers. Today, visitors can horseback ride, hike, bike, and cross-country ski on nature trails across 1,520 acres of woodland, meadows, rock shoreline, and salt marsh. Fishing and even scuba diving (with a permit) are also allowed on site. The Caumsett Café offers drinks, snacks, wraps, and salads.
13 minutes by car or 32 minutes by bicycle from Huntington
7. OHEKA Castle, Huntington
This famous French-style château estate has appeared in countless movies and TV shows, from Citizen Kane to HBO’s Succession. Built by financier Otto Hermann Kahn in 1919, it stands on the highest point in Long Island. At the time of its construction, the 123-room, 109,000-square-foot castle was—and still is today—the second-largest private residence ever built in the United States.
The estate hosted countless parties during its heyday in the Gilded Age, but when Kahn died in 1934, it changed hands several times, at one point becoming a military academy, which bulldozed the gardens. After the academy left, it was abandoned for several years—until developer Gary Melius purchased it in 1984 and restored the grand building and grounds to its former glory.
Today it functions as a luxury hotel with a fine dining restaurant, Ohk Bar & Restaurant, serving American steakhouse-style fare. Mansion tours are available.
9 minutes by car or 21 minutes by bicycle from Huntington
8. Bayard Cutting Arboretum, Great River
Located near Great River Islip on the South Shore, Bayard Cutting may not be on the Gold Coast, but it’s still every bit as impressive as the rest of the estates on this list, thanks to a stunning landscape designed by Frederick Law Olmsted in 1887 that stretches across 691 acres. Formerly the home of railroad magnate, lawyer, and developer William Bayard Cutting and his family, the Tudor Revival-style mansion and grounds are just across from Fire Island.
Today, the extensive gardens are open to the public. Public and private tours of the grounds are offered (except in winter), as well as private tours of the manor house for groups of 10 or more. You can get a peek inside though if you visit Hidden Oak Café, which is located inside and offers breakfast, lunch, and Victorian high tea, complete with finger sandwiches and scones.
11 minutes walking or 4 minutes by bicycle from Great River
Devorah Lev-Tov is a travel and food writer based in Brooklyn. She has been living in NYC for 15 years and writes for publications including The New York Times, Travel + Leisure, Conde Nast Traveler, Vogue, Bon Appetit, Food & Wine, Eater, Thrillist, and more.