Halloween is a magical time on Shelter Island, falling leaves, pumpkins in every size and shape lining stairs and guarding doorways and huge inflatable ghouls that lie like colorful wreckage during the day.
The Halloween parade (on Monday, October 31 at 4 p.m. in the Center) is one of the best parts and gives us adults a chance to see the costumes and be part of the festivities after we’re not allowed to accompany our children trick-or-treating anymore. Anyone can participate, dressed in whatever their imaginations can dream up: dogs dressed as hot dogs or cowboys, mortified expressions on their doggie faces; a baby slumped in a wagon decked with flowers; an Eskimo, a mime and sixth grade boys, unafraid to dress as girls or the Tooth Fairy. Last year, there was a boy dressed only in a blue towel and shower cap, fake suds cascading down his shoulders. It was a clever costume but maybe not the best choice for late October in New York, as you could see the goose bumps from across the street.
The parade is followed by a party at the firehouse where the Fire Department Auxiliary hands out trick-or-treat bags and hot dogs, so at least the kids have something in their stomachs besides candy, before the main event of trick-or-treating on Smith Street.
Our first Halloween here, somewhere between the parade and Smith Street, we lost track of our sixth grade son. For an hour and a half, we never saw him. He was with friends, so it was okay. This was Shelter Island and someone knew where he was; he was safe. We finally met up with him at Chrissy Gross’s house.
Chrissy is the Queen of the Halloween scene. At the corner of Smith Street and South Ferry Road, her house is the end of the line for trick-or-treaters. To get her goody bags, kids have to go under the huge inflatable tree, its glowing eyes watching, into the fog, up the stairs and into the house, where two witches hand out candy. Afterward, they can take a walk around the yard — if they dare. Watch out for “Marcus the Carcass” with only his head, hands and feet sticking out of his grave, the huge inflatable scarecrows with pumpkin heads and the dragster, complete with Dracula, just emerging from his coffin. The community donates all of the candy for Smith Street residents to hand out. Chrissy and her volunteers put together close to 300 bags of treats every year for her own house.
Our reputation as the place to trick or treat even crosses the moat, as kids from Sag Harbor and other far-flung places take advantage of our Island generosity.
There were years when Joanne Calabro hosted a haunted graveyard at St. Mary’s Church. Joanne plundered her impressive collection of Halloween decorations and the teenagers would chose their roles, outfits and accessories from boxes filled with costumes, toy chain saws and more fake blood than was ever seen outside of a horror movie. The hall was transformed into a spooky place, complete with an 8-foot-tall inflatable Grim Reaper arch that had to be passed through to gain entrance.
The graveyard was strung with lights and fake spider webs, eerie music emanating from somewhere in the darkness and featured “tours” of the graveyard. The teenagers were not supposed to scare the little kids, the ones who clutched their glow necklaces like protective amulets. But some of those intrepid kids wanted to be scared. They’d walk off the lit path, away from the group, daring to look at the dead bride, covered in blood, the banquet table that had a real head served on a platter, stifling a scream when a kid wielding a plastic chain saw jumped from the bushes. A recent grave added to the creepiness.
Halloween is a time when we come together, after the hectic activity of the summer. We look around and see friends we may not have seen in awhile and celebrate a child’s holiday.
If a community defines itself, in part, by the way it celebrates its holidays, then no place does it better than Shelter Island.