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Hamptons.com
August 31, 2020

Sixty-Something: Unique Shelter Island Stands Alone

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

Every summer, I make a few visits to Shelter Island – both by sailing there and by taking the South Ferry or North Ferry with my car. Part of my first full-time, paying job in the Hamptons was delivering a weekly free magazine to Shelter Island once a week for almost four years. A magazine that had my articles. I still remember that snowy February Friday morning I was the only vehicle on the South Ferry both coming and going. Driving between the coldest, whipping wind, forming ice everywhere and the wicked snowy roads conditions was an adventure. Yet, the memory of that whole day is my favorite. You see at almost every drop off location during that storm was someone who said, “Good morning.” With many offering coffee. Yes, everywhere looks new and different with a foot of snow.

However, my last two visits to Shelter Island was this week. One by sailboat and one by car, both on 80-plus weather days with fantastic soothing sea breezes. You see there is something special about a small Island only accessible by ferry or some other kind of boat.

Many say Montauk is the “Unhamptons.” Well, Shelter Island is something much more because it is pure Americana. It is as if Norman Rockwell designed every home, building, and inn – because everywhere you look you see majestic historical homes that give you the feeling you have both gone back in time and are visiting somewhere with a huge soul. It is true that Shelter Island has been a summer vacation home Mecca for over a hundred years, and in August on weekends it gets “busy,” but that ferry acts as a gatekeeper to screen out annoying folks and people who don’t like to be inconvenienced. It is a place for quiet serene moments and for extremely high quality time with families, or even by oneself. For the locals, it is so much more – it is their home, to protect, and safeguard.

Although many hot spots were still maneuvering to adhere to the ever changing safety protocols to prevent the Coronavirus, it was tragic to drive down to Crescent Beach, known to many as Sunset Beach, on a hot, sunny August Sunday and see the Sunset Inn boarded up. I have had so many wonderful experiences there over the last thirty years that seeing it boarded up like a condemned property was sad. I am sure it will be back next summer serving wonderful international meals and mixing up some of the best mojitos on earth.

The author with his Marie Eiffel Market lobster roll. (Courtesy Photo)


However, open for business was Marie Eiffel Market. I believe at this venue the best lobster roll on the East End is prepared and sold on a very tasty very French “brioche.” Of course I sampled one.

Dering Harbor is a post card view in every direction, every day of the year. Sailing into Dering to tie up at the town dock is a ritual I have now done a few times every summer for seventeen years. This last weekend, the harbor was buzzing with multiple size sailboats and power boats, along with a few kayakers and paddle board enthusiasts. In every direction you look, you see beautiful boats. However, that February snowy day, only a single commercial fishing boat was in that whole harbor.

Last week, I achieved a first. I literally sailed without motor from my Three Mile Harbor slip to the Shelter Island Rams Head Inn dock at the end of Coecles Harbor never using my motor! Coecles Harbor has an entry of about twenty yards wide at high tide and other than dead center past the green buoy, it can be only a foot deep. To sail in safely, you need the right wind, the right tide, and a lot of nerve. Coecles Harbor, Shelter Island is a favorite day trip or overnight destination for many boaters.

Lastly, I cannot write about Shelter Island without mentioning I love small car ferries! I love standing amongst the cars feeling the boat vibrate from the powerful engine that fights all winds, all currents and all weather dozens of times every day all year round. When it leaves the dock, I become but a boy enjoying the short ride to a magical place.

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

December 21 @ 03:00 PM - December 21 @ 04:00 PM
Montauk Library
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21
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21
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Pop-Up Chanukah: Eitan Levine

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