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Hamptons.com
December 2, 2023

Sixty-Something: Holiday Season in the Hamptons

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T.J. Clementeby T.J. Clemente
in Community, Trending
Home Community
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.

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Over the past week, there were 21 Listings that went into contract from Westhampton to Montauk.




Compared to this same week last year (2025), there were 20 Listings that went into contract.




Which is a year over year INCREASE of 5%.

This same week in 2024, there were 28 Listings that went into contract.

Compared to this past week, there was a DECREASE of 25%.

Hamptons Real Estate Market Data – Week of 7/14/2026

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Which is a year over year INCREASE of 5%.

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  • Sant Ambroeus has become one of the East End’s most beloved dining destinations. The place has style, serves gelato and espresso all day, offers inviting outdoor seating, and delivers a world-class dining experience.

Their fresh pasta is made with eggs, and doesn’t weigh you down like other pasta does. The signature branzino dish has become a calling card for the Southampton location.

No visit is complete without a stop at the gelato counter, where handcrafted gelato and sorbetto are churned in-house, offering a cool, classic finish to a summer meal.

You’ll see me there again sipping an espresso and pretending to be Italian. Diet starts tomorrow.
  • Ralph’s Coffee is popping up at Mulford Farm for the summer season. Stop by from 8am - 5pm for specialty drinks, pastries, outdoor seating, and lawn games until September 7th.
@ralphscoffee 
#Popup #ralphscoffee #coffee
  • Today, @childrensmuseumoftheeastend hosted its 16th Annual Family Fair in Bridgehampton, raising funds for its on-site food pantry, providing summer camp scholarships to local children, and supporting other initiatives that serve East End families year-round.

A special thank you to CMEE and lead event sponsor Saunders & Associates for welcoming us to capture the day’s magic.
  • We stopped by Pre-Loved in Montauk to see where founder @sunnymelet sources her vintage pieces. You can visit Pre-Loved any day of the week from 10am - 6pm.
@prelovedmtk
  • Last week, Rebecca Minkoff, alongside RummiKlubLA founders Laura Galvan and Marnie Wekselblatt, celebrated the launch of their first collaboration, a limited-edition blue terrycloth RummiKlubLA game set, with a Hamptons-style game day at the picturesque Maidstone Inn in East Hampton.

The limited-edition game set features a vibrant cobalt-blue terrycloth carrying case, playing pieces, and racks featuring the signature Rebecca Minkoff logo. The set feels luxurious and is a summer essential.
@rebeccaminkoff @rummiklubla

#rummikub #rebeccaminkoff #easthampton #maidstone #collab
  • If you’re into Mediterranean cuisine, Calissa is the spot for you. From the moment you arrive, you’re greeted with complimentary valet parking, amazing front-of-house staff, and an oasis of Greek fine dining. The place runs like a jet engine: an open kitchen, sexy interior, an energetic environment, a long bar, and an enormous outdoor dining area.

We sat down and started with the Saganaki, the world-famous fried Greek cheese. They do it right at Calissa: coated in sesame seeds and drizzled with fresh honey, the dish is a flavor bomb. I recommend ordering the steak here, it comes out cooked perfectly with fresh tomatoes. We also tried the grilled octopus, which is listed as an appetizer but could easily stand in as your entrée if you’re looking to eat a little lighter that evening.

If you feel like dancing, the restaurant transforms into a lively bar after 10pm making for a real Hamptons memory. The entire evening at Calissa is special. Highly recommend.
@calissahamptons
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