4 Gatsby-Style Celebrations to Kick-Off the Holiday Season

This holiday season, do as Jay Gatsby did. (You just might want to leave your yellow Rolls Royce at home.)

vanderbiltmuseumchristmas-courtesyvanderbiltmuseum

Christmas at the Vanderbilt Museum • Photo courtesy of the Vanderbilt Museum

To this day no one does glamorous soirée better than the captains of industry who once called Long Island home. From the Vanderbilts to the Guggenheims, these self-made American royal families not only helped build our country, they defined play hard, commissioning gorgeous homes across the island that served as the setting for the lavish parties they threw. While, sadly, many of the estates that once provided the industrialists with the ultimate getaway have crumbled, a few have been preserved and some are open to the public. This holiday season experience the swoon-worthy Gatsby lifestyle of the past for yourself when four mansions decked out in holiday finery throw open their doors for elaborate dinners, high teas and of course tours.

Hempstead House in the snow • Courtesy of Sands Point Preserve Conservancy

Hempstead House in the snow • Courtesy of Sands Point Preserve Conservancy

Not Quite Christmas Cabaret
Saturday, December 3, 6:00-10:00 p.m.
Hempstead House at Sands Point Preserve
27 Middle Neck Road, Sands Point
$125-$250

The Guggenheims of Sands Point were partiers. They threw extravagant, lavish celebrations at Hempstead House, mostly during the summer, but every holiday season the Sands Point Preserve Conservancy, hosts “Not Quite Christmas Cabaret,” in their former home. The annual holiday concert begins with cocktails for VIP ticket holders in the breakfast room, where windows offer a view of the expansive grounds. Dinner and the concert featuring a cast of Broadway performers, follows. If the concert isn’t your speed you can venture into Hempstead House later in December for Christmas stories and carols.

Old Westbury House • Photo by Vince Kish

Old Westbury House • Photo by Vince Kish

House Tours & Visits With Santa
Saturday & Sundays, December 3-18
Old Westbury Gardens
71 Old Westbury Road, Old Westbury
$7-$12

Tucked into 200 acres of gardens, landscaped grounds and woodlands, Westbury House was built by a British designer for the Phipps family in the early 1900s. Every year the place becomes a holiday dream—rooms decorated with Christmas trees, wreaths and other topiaries and antique furnishing and toys displayed make it the perfect setting to visit Santa or tour the house in all it’s splendor. The holiday offerings at Old Westbury Gardens this season include crafts for kids, wreathing making classes and chocolate and tea pairings. Check out their website for the full list of opportunities.

Holiday Dinner
Saturday, December 3, 6:00 p.m., and 8:00 p.m.
Vanderbilt Museum
180 Little Neck Road, Centerport
$115 ($100 for members)

With breathtaking views of Northport Bay, it’s no wonder one of America’s most famous families loved to entertain at the elegant, mansion once called Eagle’s Nest. To kick off the 2016 holiday season, the Vanderbilt Museum opens up William K. Vanderbilt’s II home for an evening in the Spanish Revival house where the Vanderbilts threw parties for Hollywood stars and European royalty in the 1930s. Enjoy wine and hors d’oeuvres in one of the galleries before taking a tour of the mansion dressed to the nines in holiday finery. Dinner is held overlooking the harbor.

West Wing of the Manor.

A photo posted by Howie Guja (@howieguja) on

Holiday Tours
Saturday & Sunday, December 10 & 11, 10:30 a.m.-3:00 p.m.
Sagtikos Manor
677 Montauk Highway, Bay Shore
$8-25

Travel deeper into America’s past at Sagtikos Manor. Built in 1697, the colonial era-house hosted both the British Army who used it as headquarters during the Revolutionary War and George Washington who later stayed in it. This year the historical society will trim the house in a Myths & Legends theme with docents celebrating a different story through decorations in each room. Tours leave every 15 minutes and take just under an hour. After the tours enjoy hot chocolate, cider or other hot beverages with cookies.

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Bridget is the digital strategy editor for Edible Manhattan, Edible Brooklyn, Edible Long Island and Edible East End.