Sixty-Something: Holiday Season in the Hamptons

It’s now December, and the holiday season is upon us. The hamlets of the East End are showcasing their festive spirit, transforming each village into a scene reminiscent of a Hallmark Card. Driving across the Hamptons after rush hour when darkness falls, a weekly ritual for me becomes a delightful experience. Witnessing the windmills illuminated with enchanting lights is a sight I can never tire of. Montauk Village, Bridgehampton, East Hampton Village, Water Mill, and Quogue, all excel in creating a festive atmosphere. However, reminiscing about decades ago when I delivered a free weekly paper throughout the Hamptons and Shelter Island, Southampton Village, with its double lanes of Main Street and Jobs Lane, adorned with charming alley shops, truly felt like Christmas. There’s a certain magic to walking its streets during this time.

This season brings with it parties, gift buying, and home decorating. Some individuals wholeheartedly embrace the holiday spirit, adding a unique personal touch to their homes with seasonal wreaths, lights, trees, and the now-popular huge air-filled inflatables that have become signature pieces. Personally, I’ve always believed there’s no place like home for the holidays, prompting me to festively adorn my home each year.

Many people enjoy covering their shrubs and bushes with multicolored Christmas lights, while others prefer basic colors such as all white, green, or blue. Some homeowners go to great lengths, either personally adorning their homes with lights or enlisting specialized help to illuminate trophy homes. I vividly recall my father, when I was young, bravely ascending a ridiculously high ladder to decorate the roof of our home. That’s a feat I could never replicate.

Then there are those who go all out with elaborate displays, featuring Santa Claus, his sleigh, reindeers, The Grinch, nativity sets, and an assortment of Christmas decor. For families with young children, creating a festive home is almost a given. In the Hamptons, many grandparents take joy in decorating for the delight of their grandchildren. While my own grandchildren reside in England, I strive to make my home as festive as possible, pulling out cherished Christmas photos from various eras.

Christmas allows everyone to revisit the past, creating new memories while cherishing old ones. Gathering the family to decorate the tree, with each person contributing to the placement of ornaments, is a tradition for many. Most families still possess ornaments crafted by their children, themselves, or even grandparents. Do you remember the days before LED lights when bulbs behaved like lava lamps due to the fluid inside?

The choice of holiday trees remains a significant personal statement. Some opt for live trees, later planting them in their yards, while others faithfully reuse the same artificial tree year after year. In the Hamptons, some embrace an old-school approach, cutting down a tree in special locations only known to them. Over the years, I’ve enjoyed the spontaneity of pulling up to a pop-up Christmas tree stand, pretending to be knowledgeable about tree selection. There was even a time when my daughters took charge of picking the tree, making the process easier. I once impulsively purchased a Christmas tree at a pop-up stand in New York City and drove it down Park Avenue in my little convertible Volkswagen, from the high nineties all the way to Gramercy Park where I was staying.

Having lived in several East Hampton locations over the years, each place held a distinct holiday ambiance. Montauk Village, my most recent residence, will always hold a special place in my heart. Singing Christmas songs at Liar’s Saloon Karaoke just before Christmas became an annual tradition during that time. Walking through Montauk Village when the entire hamlet is aglow and decorated is a truly special experience. Yet, it was my one year living in the heart of East Hampton Village that stands out as perhaps the most magical Christmas I’ve ever had. Late on Christmas Eve, a sizable group of us, without our families nearby, enjoyed a late (until midnight) dinner at the Palm. As the evening concluded at midnight, with snow flurries in the air, the nearby church bells began to chime through the wispy snowfall. I continued to hear them as I walked home, no more than an eighth of a mile. It was as magical as Christmas can get.