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Hamptons.com
December 2, 2023

Sixty-Something: Holiday Season in the Hamptons

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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​Saturday Camp AM Drop Off: 12/20 Gingerbread Baking at the Green School!

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Blackbook Art Gallery’s Holiday Party

December 20 @ 11:00 AM - December 20 @ 04:00 PM
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Consonance Music Ensemble in Bridgehampton

December 20 @ 01:00 PM - December 20 @ 03:00 PM
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  • 🎄 This Weekend in the Hamptons 🎶✨⁠
⁠
🎷 Hamptons JazzFest Presents: NYC Spirits⁠
📅 Fri, Dec 19 | ⏰ 6:30–9pm⁠
📍 Masonic Temple, Sag Harbor⁠
An evening of world-class jazz⁠
⁠
🎻 Candlelight: Christmas Carols on Strings⁠
📅 Sat, Dec 20 | ⏰ 6–7pm⁠
📍 Guild Hall, East Hampton⁠
A magical concert where music and visuals meet⁠
⁠
🍷 Winter Wonderland at Wölffer Estate Vineyard⁠
📅 Sun, Dec 21 | ⏰ 11am–2pm⁠
📍 Sagaponack⁠
Festive drinks, cozy firepits & family fun⁠
⁠
🕎 Pop-Up Chanukah: Eitan Levine⁠
📅 Sun, Dec 21 | ⏰ 5–7pm⁠
📍 Guild Hall, East Hampton⁠
Comedy, community & a menorah lighting⁠
⁠
🚂 The Polar Express⁠
📅 Sat, Dec 20 – Sun, Dec 21⁠
📍 Southampton Playhouse⁠
A holiday classic on the big screen⁠
⁠
❄️ Igloos by the Sea at Gurney’s⁠
📅 Fri, Dec 19 – Mon, Dec 20 | ⏰ 5pm & 7pm⁠
📍 Montauk⁠
Heated oceanfront igloos with festive bites & cocktails⁠
⁠
📚 Light, Sand and Sea Book Signing⁠
📅 Sat, Dec 20 | ⏰ 5–8pm⁠
📍 Baker House 1650, East Hampton⁠
A Hamptons-centered book celebrating local artists⁠
⁠
🎶 Consonance Music Ensemble at Marders⁠
📅 Sat, Dec 20 | ⏰ 1–3pm⁠
📍 Bridgehampton⁠
Holiday shopping with live music⁠
⁠
👉 Click the link in bio for more events⁠
⁠
#hamptons #guildhall #holidays #hanukkah #booksigning igloos livemusic winterwonderland wolffer
  • The Southampton Playhouse, located at 43 Hill Street in Southampton, has quickly reestablished itself as one of the East End’s most vibrant cultural spaces. After an extensive renovation and a reimagining of its mission, the beloved historic theater is once again bringing people together through film, conversation, and community.⁠
⁠
Under the leadership of Executive Director Maria A. Ruiz Botsacos and Artistic Director Eric Kohn, the Playhouse has evolved into a dynamic hybrid of state-of-the-art cinema and community arts hub—offering everything from IMAX blockbusters and 35mm classics to live performances, themed series, and exclusive talks with filmmakers.⁠
⁠
Read the full interview at Hamptons.com (Link in Bio)⁠
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#southampton #southamptonplayhouse #hamptons #film
  • On Saturday, December 13th @heartofthehamptons held their annual Polar Bear Plunge at Coopers beach in Southampton. 

The whole community came together for treats and plunged for a great cause ❄️

#polarbearplunge #coopersbeach #southampton #heartofthehamptons
  • HamptonsFilm announced that the 34th annual edition of the Hamptons International Film Festival will take place October 2-12, 2026. The 11-day festival will feature screenings and events across the Hamptons.⁠
⁠
HamptonsFilm announced that the 34th annual edition of the Hamptons International Film Festival will take place October 2-12, 2026. The 11-day festival will feature screenings and events across the Hamptons.⁠
⁠
The festival will begin accepting submissions via FilmFreeway in February. ⁠
⁠
“As we look ahead to the 34th edition of the Hamptons International Film Festival, we’re excited to continue to bring audiences eleven days of screenings and events across the East End,” said David Nugent, Chief Creative Officer of HamptonsFilm. “Each year, our filmmakers and audiences inspire us to grow, experiment, and celebrate bold new voices in cinema. With submissions opening in February and an exciting slate of year-round programs, from our Screenwriters Lab to SummerDocs and our beloved outdoor screenings, we can’t wait to welcome everyone back this October.”⁠
⁠
⁠
Read the full article at Hamptons.com (Link in Bio)

#hamptonsfilm #filmfestival
  • Check out the Top Hamptons Events This Weekend!

Hampton Ballet Theatre School’s 16th Annual Nutcracker at Guild Hall
When: Fri, Dec 12 – Sun, Dec 14, 2025 • 7pm, 12pm & 5pm
Where: Guild Hall, 158 Main Street, East Hampton, NY
Get into the holiday season with a timeless ballet!

Polar Bear Plunge in Southampton
When: Sat, Dec 13, 2025 • 9am–11am
Where: Coopers Beach, 268 Meadow Lane, Southampton, NY
Celebrate 22 years of getting freezing for a reason! 

Holiday Tour of the Inns
When: Sat, Dec 13, 2025 • 1pm–4pm
Where: East Hampton, NY
Enjoy festive décor and treats across East Hampton’s charming inns.

A Holiday Moment in The Hamptons
When: Sat, Dec 13, 2025 • 2pm–6pm
Where: 26 Montauk Highway, Amagansett, NY
Walk through the evergreens and enjoy cocoa, cider & treats benefiting the Eleanor Whitmore Early Childhood Center.

Amagansett Life-Saving Station’s 3rd Annual Tree Lighting & Toy Drive
When: Sat, Dec 13, 2025 • 4pm–5:30pm
Where: 160 Atlantic Ave, Amagansett, NY
Arts & crafts, cookies, hot chocolate, music — and bring an unwrapped gift for the Kiwanis Toy Drive!

A Christmas Carol: A Live Radio Play — Hampton Theatre Company
When: Fri, Dec 12 – Sun, Dec 14, 2025 • 7pm & 2:30pm
Where: Quogue Community Hall, 125 Jessup Ave, Quogue, NY
A festive classic returns for one weekend only!

Pop-Up Chanukah at Herrick Park
When: Sun, Dec 14, 2025 • 4pm–6pm
Where: Herrick Park, 67 Newtown Ln, East Hampton, NY
Celebrate with songs, donuts, gifts for kids, a dreidel drop & the lighting of the public menorah.

Breakfast with Santa at The Hampton Maid
When: Sun, Dec 14, 2025 • 8am–1pm
Where: 259 E Montauk Hwy, Hampton Bays, NY

Montauk Holiday Concert
When: Sun, Dec 14, 2025 • 3pm & 4pm
Where: Saint Therese of Lisieux, 67 S Essex St, Montauk, NY
Enjoy holiday classics!

Santa Selfies with Birds of Prey
When: Sat, Dec 13, 2025 • 1pm–3pm
Where: Marders, 120 Snake Hollow Rd, Bridgehampton, NY
Meet rescue birds from the Evelyn Alexander Wildlife Center!

Gifts & Carols at the Nathaniel Rogers House
When: Sat, Dec 13, 2025 • 4pm–6pm
Where: 2539 Montauk Hwy, Bridgehampton, NY
Sing along with the Dickens Carolers!

For all event details, see the link in bio. 

#hamptons
  • Saunders & Associates once again demonstrated its commitment to the East End community with the 12th Annual Thanksgiving Donation Drive, which this year reached a record-breaking milestone. ⁠
⁠
Coinciding with Giving Tuesday, the campaign raised an impressive $62,000 for Hamptons food pantries—making it the most successful drive to date and significantly expanding support for local families during the holiday season.⁠
⁠
As the Hamptons’ leading real estate brokerage, Saunders & Associates’ annual Thanksgiving Donation Drive underscores the firm’s longstanding commitment to supporting the Hamptons community all year long.⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptons #saunders #community #foodpantries
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