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How to Celebrate Halloween Like a Hedge Fund Boss

How does the urban luxury class celebrate Halloween in New York City? Do they even notice it? You might be surprised to learn that like many other Americans, the wealthy financiers of the Upper East Side of Manhattan love Halloween. We can’t say whether or not it’s their favorite holiday, but it has to be in their top 5. How else to explain the over-the-top decorations currently gracing the quiet tree-lined side streets of the tony Upper East Side? Here at Dandelion Chandelier we’ve been on a mission to investigate the most luxurious Halloween experiences. We posed the critical question of town or country: is the perfect Halloween rustic-chic, surrounded by trees, pumpkins and hay bales? Or is it big-city glamorous, with stately townhouses decorated in the most sinister possible way? If you live in or are visiting greater New York, you have to go to The Great Jack O’ Lantern Blaze, which is the perfect rural Halloween road trip. But if you want pavement under your feet and big-city glamour, head to the Upper East Side between Fifth and Park, between 65th and 79th Streets. In that small, highly wealthy enclave, you’ll find lots of crazy-fun Halloween decorations – and some seriously beautiful historic brownstones.

We went out on a reconnaissance mission a week before October 31st, and here’s what we found:

–East 78th and Fifth is a great starting point for your Upper East Side Halloween crawl. On that block, on the south side, you’ll find a fanciful brownstone wrapped in faux spider webs and crime scene tape. A nattily-dressed skeleton with a red bow-tie and red pants lounges at the foot of the front steps, and ravens, huge black spiders, and bats hover near the oversized picture windows. There’s a mini-graveyard in the front garden with a hand-painted sign warning “Keep Out.” Black lanterns, pumpkins, and random skeletons line either side of the entrance, and the sidewalk in front of the home has been declared a Zombie Crossing. Duly noted.

–East 74th between Park and Madison has two lovely, understated brownstones with a slim and chic witch, a reclining skeleton, a Calvin-Klein inspired ghost, and a bat affixed to a gorgeous wrought-iron metal door. A golden glow emanates from inside, even by day. We totally want to go to their party. They seem like people who would serve really good food.

–We found a sweetly whimsical display on East 73rd between Fifth and Madison. A witch has had a mid-air collision with a handsome Georgian red-brick townhouse that is adorned with autumn leaf garlands, pumpkins, seasonal flowers and tiny colored spiders. We imagine she got distracted looking at the lovely setting and slammed right into the house. We think she’ll be OK. This kind of thing is common this time of year.

–On 72nd Street between Madison and Park (on the north side of the street), there’s a townhouse covered head to toe – all the way up its 5 stories to its roof – with every possible creepy, bloody, spooky, outrageous Halloween icon imaginable: a witch guards the door, the main stairwell is lined with bleached white skulls and rustling corn stalks; and an enormous spider leers at passersby from the front bannister. The lower entry is awash with corpses, gargoyles, rattling chains, skeletons, The Grim Reaper, an undertaker, numerous coffins, a dismembered robot and a mad doctor. Plus a fire-breathing dragon. The trees are hung with shrunken heads, witches caught in mid-shriek and ghosts. Gravestones line the perimeter of the property. In each of the picture windows on the upper floor of the property, there are various monsters, scarecrows and ghouls. In case anyone is missing the point, there’s also a helpful sign pointing the way toward the Haunted House. Yep, we figured that out, but thanks anyway! It’s pretty freaky by day, and at night, it’s a real scene. Expect crowds posing and taking pictures both night and day through November 1. The home is rumored to be owned by a media executive or a Loeb. No one is quite sure. But whoever owns it has a great sense of humor.

–69th Street between Fifth and Madison seems positively tame by comparison: a gracious townhouse there boasts hay bales, bright red and orange peppers, scarecrows, zombies, witches, pumpkins, and a collection of bodies wrapped in shrouds, hanging upside down from the doorjamb (they kind of look like cocoons, actually). You could bring a small one here and they would not be even remotely put off or frightened. However, if you’re looking for a serious scare, this is going to feel way too cheerful for you.

–The final stop on our little tour was a townhouse on East 67th between Fifth and Madison. Owned by hedge fund manager Phil Falcone, this home is always Halloween Central. The black wrought-iron gates are covered with thick blankets of spider webs. A zombie family, all dressed up, walks its skeleton dog. The second-floor bay windows host a trio of black-clad witches (Shakespeare’s Weird Sisters, perhaps?) Skulls nest in the grilles of the gates, and the ornate front door is guarded by a witch, a bloody corpse, and two quite cheerful jack-o-lanterns. The small front yard has been transformed into a “high voltage” gate-guarded zombie prison – like the Walking Dead, this guy moves, and he scared the bejeebees out of a little one passing by. In a nearby shrub, an enormous horned swamp creature menacingly raises his arm. A group of tourists from Central Europe took this as an invitation for a selfie while we there.

That did make us wonder; what on earth do the tourists from other countries make of all of this Halloween excess in our country? Do they think we’re crazy? The ones we saw on our Upper East Side crawl were having a fine time with it all. Maybe it makes even the richest Americans seem more human.

On Halloween itself, the tradition has been that a couple of streets on the Upper East Side close to traffic between Fifth and Park, so that kids and their families can trick-or-treat and have a big block party without fear of vehicular traffic. Some apartment buildings are full of trick-or-treaters going floor to floor, as well. If you decide you’re more of an Upper West Side type, head for West 69th Street between Central Park West and Amsterdam; it’s a big block, entirely decorated for Halloween, and there’s lots to see. And of course, there’s the annual Greenwich Village parade on Halloween night, stepping off at 7:00P for the 44th time. The route runs straight up 6th Avenue, from Spring to 16th Street. You have to be in costume, but anyone can march in this parade (a friend did it last year for the first time, and he loved it).

We’ve previously shared our ideas about the perfect luxurious Halloween treats and the best ways to add some chic bling to your Halloween costume. Now it’s up to you. Happy Haunting.

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