Chimney Stories: Santa Delivers to Indians, Settlers, Whalers, Visitors

Before the Hamptons was “the Hamptons,” Santa was making his regular Christmas deliveries by reindeer and sleigh to the Native Americans who lived here. They were the Montauketts, the Manhansetts, the Shinnecocks and a host of other tribes.

The Indians did not live in teepees, they lived in domed huts with holes at the top to let out the smoke from fires inside. Santa had no problem with the huts when the residents would remember to put the fires out on Christmas Eve. He’d land by the holes and drop the presents down. But on very cold days when the residents would either forget or decide not to put the fires out, he’d early on pass up on those Indian residences. This led to an outcry. But in the end, Santa solved it by strapping bags of gifts to the tops of the domes where the fires were. And everyone was happy. The parents made a game out of scrambling up to the top to get the gifts. The children loved it.

In colonial days the settlers built a total of 13 wood-shingled windmills throughout the East End to grind corn into flour to make bread. Nearly all of them remain today, treasures of this community. One year, Santa’s sleigh knocked one of the blades off a windmill on a hill in Southampton as he came in to land on a roof. After that, the settlers put Christmas tree lights up on the blades. They do this to this day. Another year, Santa’s elves decided to give every kid in the Hamptons little toy windmills, six inches high. Hundreds and hundreds of them were made. The kids were puzzled to receive them. They spun the blades around for a few minutes and then set them aside. The parents sent Santa a letter asking he not do that again. He didn’t.

On Christmas Eve during the War of 1812, when the British landed at Long Wharf, hoping to march into town and burn the place to the ground, a pitched battle took place between them and the locals. The locals knew the British were coming ahead of time. They had been tipped off. So beforehand, they evacuated the women and children to Bridgehampton. Santa started going down the chimneys of the houses in Sag Harbor around midnight in the middle of the battle, but quickly people told him what was going on, and so instead of finishing up he went to Bridgehampton with double rations and a note telling the kids of Bridgehampton to share, which is what they did. By the way, in the end, the British were driven off.

Around 1830, another problem developed in Sag Harbor. In those years, Long Wharf in that town was home to over 100 whaling ships that sailed the seas as far off as Japan, Australia and China. Many homes were built with wooden hatches that opened up onto the top of the roof. People, especially women, could go up into their attics and, with a wooden ladder, climb up inside and peer out, hoping to see the ship bearing their husbands coming back home to port after a yearlong absence. At that time, when a ship would be sighted heading in, low in the water because of the caskets of whale blubber on board, church bells would sound and the “widows” would head up top.

This resulted in Christmases, on several occasions, with Santa climbing down the hatches and leaving the bags of presents in the attic. It took a while before the parents of the disappointed children figured out what was going on. After that, there was this famous catchphrase in town: “Not in the fireplace, look in the attic.” It worked.

By the way, some of the wealthier ship captains built entire covered platforms up there for their wives. They were called “Widow’s Walks,” because some were big enough for the wives to pace back and forth on. You can see some of them on rooftops in town today, although there hasn’t been a whale ship come into town in 150 years.

About 1860, wealthy New Yorkers began coming out to the Hamptons by train to giant summer residences they built. They had no intention of occupying them after the summer ended. Most didn’t even have heat. The idea was to enjoy the “fresh air” of the summer away from the city, and then, at Labor Day, leave town and not return until the spring.

This created serious problems for Santa Claus, because he couldn’t tell which houses were occupied and which not. Some families would arrive back at their summer homes in June to find presents in the fireplace. They were delighted at first, but then, when they realized the situation, they discussed things with the townspeople and it was decided to put up a little red flag on a chimney top when they left to go back to the city at Labor Day. Still today, you sometimes see a red flag on a chimney on a big house.

Around 1920, telephone poles were built throughout America to provide electricity to all the houses. Santa opposed this at first, saying that his reindeer and sleigh could get tangled up in these wires, but then, when they electrified the North Pole workshop and his home, he changed his mind. As a result, at that time he obtained the services of a reindeer named Rudolph, who had a very shiny nose that glowed. With that, Santa and his reindeer worked out various flying maneuvers to get over or under the wires where he encountered them.

During World War II (1941–45), there were times when “blackouts” were ordered for the Hamptons and elsewhere. Residents were required, after sundown, to close the curtains on all windows and keep all the lights off until dawn. There was fear that the Germans might conduct air raids over America and the idea was that if no lights were on in a town or city, the pilots would be unable to see their targets.

This was very successful. No German planes ever bombed the East Coast. But it did cause distress for Santa Claus. For one thing, one night when a blackout coincided with Christmas Eve, he couldn’t even find eastern Long Island, much less the Hamptons. The reason was, he had to abide by the law as did everybody else, which in his case meant he had to switch off Rudolph’s nose. After that, secret negotiations were conducted between the Americans and the Germans, and with an agreement that the Germans wouldn’t bomb on Christmas Eve, everything returned to normal.

Today, celebrities occupy many houses in the Hamptons. When they first started coming here, this presented another kind of problem. Inside the houses, the children lay in their beds, dreaming of sugarplums and waiting for their presents. But up on the roofs, security men, hired by the celebrities and always on the lookout for paparazzi trying to sneak in to photograph where they shouldn’t, mistook the sound of sleigh bells for an arriving celebrity magazine helicopter. A whole incident happened that first year, but after that Christmas, it all got sorted out.

Today when Santa approaches, all he has to do is shout “ho, ho, ho” and the security men hop to it, directing the sleigh to a proper landing and keeping guard on him as he slides down the chimneys to leave off the presents.

And so, today, Christmas remains a wonderful time. And everything has been all worked out. It is a day to celebrate the birth of our Lord and, well, you know the rest.