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Hamptons.com
October 7, 2023

Sixty-Something: Living Out Your Dreams on the East End

T.J. Clementeby T.J. Clemente
in Community, Trending
Home Community
Sixty-Something: Living Out Your Dreams on the East End

Throughout my life, I have heard the word “dream” used in many ways: dream job, dream house, dream car, dream date, and so forth. When you reach your sixties and beyond, you start making decisions to perhaps take aim and achieve some of your dreams. Over the last twenty years, I have watched so many people actualize living out their dreams on the East End. We all know the stories of dreams coming true on the East End.

 

Ever since there was a 1960s TV show called “Route 66,” I have desired a 1963 Corvette. Of course, at this late stage of life, I can actually buy one, I just never will. I have actually only driven in a Corvette once in my life, and disliked the ride; the same thing with Porsches and Ferraris. They ride too tight and hurt my ribcage. I find it ironic how many folks my age are now owning and driving brand new Corvettes and Porsches, realizing it’s now or never.

 

On the East End, I believe there seems to be a trend of successful people late in their lives who have decided to invest all their time and resources to concentrate on their dream of painting, doing photography, playwriting, or trying to finish a novel. The energy from the natural beauty of the East End seems to inspire many folks to be creative. I know I am one of those folks. In the Hamptons, it does seem normal to have a judge and a few town supervisors who, besides their jobs, just love to be up in front of people singing and playing live music all over the East End. Quite frankly, they are all talented. It’s not just local politicians who have the musical bug. Up until these last few years, billionaire Ron Perlman of Revlon had a yearly blowout party at his Wainscott estate named “The Creeks” to help raise money to support the Apollo Theater in Harlem. He would have first-rate talent from Jon Bon Jovi to Blake Shelton at these parties playing songs and performing with a huge fun jam, usually with him on the drums!

 

The dock in Sag Harbor in the summer has a lineup of multi-million-dollar yachts, often with a car or helicopter mounted on them. I guess for folks like Johnny Carson, having their multi-million-dollar yacht docked in Sag Harbor was a dream realized. I remember sailing one afternoon in Gardiner’s Bay and seeing a huge superyacht anchored in the middle of the bay. Suddenly, my sailing buddy Todd pointed to a helicopter in the sky, and then in total amazement, we both watched it hover over the top level of this megayacht. While this helicopter poised off the top deck, a man in a business suit with a briefcase disembarked from the helicopter and walked onto the boat as the helicopter flew away. I still have the video footage on my iPhone!

 

Folks have different dreams. When I was a very young man, a close friend told me while sipping a beer that his dream was to have his wife’s name on his private jet and his girlfriend’s name on his helicopter and have them shop together in Milan buying him clothes. The funny thing is this same dude has been married to the same woman for 50 years now. Funny what true love can do to dreams.

 

I remember a few years back the trend was to buy Bridgehampton horse farms. Madonna and Matt Lauer were two names I remember who bought horse farms in Bridgehampton in that era. I know I have often driven the back roads admiring those horse farms. They are trophy properties of the Hamptons.

 

I was actually assigned to cover a property being sold to the Village of East Hampton that had huge sculptures on it. At that time, Sasson Soffer, an 80-year-old world-renowned artist who lived in Amagansett and New York City, owned some wooded land off Town Road. I believe over the 19 years he owned the property, he had placed 30 of his large and small sculptures there. I actually went and inspected them. His plan was for a town-owned sculpture park that would be named Grandeland. He only wanted six of his sculptures to be the only artwork displayed. Mr. Soffer’s arts foundation was to pay for installing and maintaining the sculptures. The town bought the land in 2006. Different folks have different dreams.

 

I am now living out my dream of sailing, writing, reporting, and enjoying being a husband and grandfather. I am now, like so many others, living out my dreams on the East End.

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LOCAL EVENTS

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Winter Wonderland at the Tasting Room at Wölffer Estate Vineyard

December 21 @ 11:00 AM - December 21 @ 02:00 PM
139 Sagg Road Sagaponack, NY 11962
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Dec
21
Dec
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21
Dec

Lori Hubbard’s Holiday Sing-Along at the Montauk Library

December 21 @ 03:00 PM - December 21 @ 04:00 PM
Montauk Library
21
Dec
21
Dec
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21
Dec

Pop-Up Chanukah: Eitan Levine

December 21 @ 05:00 PM - December 21 @ 07:00 PM
Guild Hall - 158 Main St, East Hampton, NY 11937
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Dec
22
Dec
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02
Jan

Holiday Camp at The Green School

December 22 @ 09:00 AM - January 2 @ 03:00 PM
The Green School, 287 Merchant's Path, Sagaponack NY 11962
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Popsicle Stick Sled

December 23 @ 02:30 PM - December 23 @ 03:30 PM
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Southampton Doctors Leading Efforts to Change Lives Worldwide

Southampton Doctors Leading Efforts to Change Lives Worldwide

  • 🎄 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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