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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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Round Pond Guided Hike

August 23 @ 08:00 AM - August 23 @ 10:00 AM
Meet at the end of Round Pond Lane, Sag Harbor.
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23
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Weekend Wonder Camp, featuring Ice Cube Paintings and Ransom Style Art (ages 5-12)

August 23 @ 09:00 AM - August 23 @ 03:00 PM
44 Meadow Way East Hampton, NY 11937
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En Plein Air with Howard Rose at the South Fork Natural History Museum & Nature Center

August 23 @ 10:00 AM - August 23 @ 01:00 PM
South Fork Natural History Museum & Nature Center, 377 Bridgehampton-Sag Harbor Turnpike, Bridgehampton, NY 11932
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Bark Jacobs by Marc Jacobs is Back at The HUB for 8/23 Only

August 23 @ 11:00 AM - August 23 @ 07:00 PM
The HUB 2183 Montauk Highway Bridgehampton, NY 11932
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STEAM: Ice Cube Painting (ages 3-12)

August 23 @ 11:00 AM - August 23 @ 12:00 PM
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INTERVIEW: Justine Green, Ed.D., Talks “Completely Me” And The Importance Of Teaching Kids That It’s OK To Be Different

INTERVIEW: Justine Green, Ed.D., Talks "Completely Me" And The Importance Of Teaching Kids That It's OK To Be Different

  • @wagsandwalks @themontaukbeachhouse 

Puppies + Pilates + @montaukila = The Perfect Day

Check out our Events Calendar for more events! (link in bio)

#wagsandwalks #animaladoption #adoptdontshop❤️ #dog #montauk #montaukbeachhouse #montaukila #pilates
  • Check out the Top Hamptons Events This Weekend! ⁠
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✨ 50th Annual Hampton Classic Horse Show⁠
📅 Sun, Aug 24 – Sun, Aug 31, 2025 | 8am–5pm⁠
📍 240 Snake Hollow Rd, Bridgehampton, NY⁠
🐴 One of the largest outdoor horse shows in the U.S., a premier summer destination for competitors & spectators.⁠
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🎶 Apollo in the Hamptons⁠
📅 Fri, Aug 22, 2025 | 6pm⁠
📍 Si Si, 295 Three Mile Harbor Hog Creek Rd, East Hampton, NY⁠
Experience the essence of the legendary Apollo Theater with DJ Cassidy, Doug E. Fresh & more!⁠
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🦈 50th Anniversary of JAWS Celebration – Montauk⁠
📅 Sun, Aug 24, 2025 | 12pm–7pm⁠
📍 Shark Bar Montauk, 2167 Montauk Hwy⁠
Screening, live music with Molly Scheider, themed cocktails, shark merch 🦈 — all to benefit Hayground School.⁠
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😂 Chelsea Handler at WHBPAC⁠
📅 Fri, Aug 22, 2025 | 8pm⁠
📍 WHBPAC, 76 Main St, Westhampton Beach, NY⁠
A night of comedy with Chelsea Handler!⁠
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🎵 The Knocks at Surf Lodge⁠
📅 Sat, Aug 23, 2025 | 4pm⁠
📍 The Surf Lodge, 183 Edgemere St, Montauk, NY⁠
The Knocks bring their signature groove to the Hamptons.⁠
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🌅 Generation S.O.S – Live From Water Mill Fundraiser⁠
📅 Sun, Aug 24, 2025 | 5pm–8pm⁠
📍 Water Mill, NY⁠
Featuring Jason Biggs, Luke K, & MC Sophie Sumner.⁠
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🇬🇷 Mykonos Nights at Calissa⁠
📅 Fri, Aug 22, 2025 | 10pm⁠
📍 Calissa, 1020 Montauk Hwy, Water Mill, NY⁠
End-of-summer vibes with DJs, drinks & dancing.⁠
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👜🐶 Bark Jacobs by Marc Jacobs at The HUB⁠
📅 Sat, Aug 23, 2025 | 11am–7pm⁠
📍 The HUB, 2183 Montauk Hwy, Bridgehampton, NY⁠
Shop Marc Jacobs & get your pup’s portrait or initials hand-painted on your accessories.⁠
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🐾 Wags & Walks’ Party Cruise⁠
📅 Sun, Aug 24, 2025 | 3pm–5pm⁠
📍 Easy Breeze Cruises, 462 W Lake Dr, Montauk, NY⁠
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🎨 5th Annual Celebrating Creatives of Color⁠
📅 Sat, Aug 23, 2025 | 11am–5pm⁠
📍 The Church, 48 Madison St, Sag Harbor, NY⁠
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#hamptons #weekend #hamptonsclassic #jaws #montauk #apollotheater⁠
  • The Southampton Animal Shelter Foundation held its “Sweet 16th” Unconditional Love Gala, a premier Hamptons event celebrating compassion, community, and animal welfare at a private estate in Bridgehampton. The Unconditional Love Gala is SASF’s largest fundraiser of the year, with proceeds directly supporting the shelter’s mission to provide care, rehabilitation, and forever homes for homeless animals. ⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#animalshelter ⁠
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  • Make sure you check out the sunset music series before the end of August. For more info on dates and times check out the Wölffer website.

#sumsetmusic #winestand #wölffer #rosé
  • Hilary Matt Interiors is a residential design firm started and located in New York City with projects spanning across the country, including in the Hamptons and East End.⁠
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Hilary, principal and founder, is known for a bold aesthetic that is comfortable and livable. She always keeps her clients at the forefront so they can express themselves as individuals through their spaces. After starting out in the fashion industry, Hilary felt a call to interior design where she has been bringing her unique approach and style to every space as the brand continues to grow.⁠
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Hilary spoke more about her background, how each HMI project differs from one another, and why the Hamptons is such a special place to her. She also shared her top 5 interior design tips as inspiration.⁠
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Can you discuss your background and how you got started with interior design?⁠
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HM: I studied business and apparel merchandising. After graduating, my first job was at a women’s contemporary showroom in NYC. I had always loved fashion and wanted to be in the industry. After a year, I realized it wasn’t quite what I expected. I had always been interested in interior design, so I took a leap of faith and accepted a job as an assistant to an interior designer. I was initially nervous to leave fashion, but I figured I could always return. I ended up loving it and worked with her for eight years, learning the ins and outs of the business. I also took classes on weekends and evenings to learn computer programs, scaling, and other essential skills. After leaving that position and having my first son, I started my own company, which has snowballed into what we are today.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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His comedy is full of observational humor and nostalgia, whether it be about his many cross-cultural experiences, an ever-changing societal landscape, and his own personal stories growing up. Des brings energy and a unique perspective to every show, evident at his Westhampton show, the place he has spent all his summers since the 90s.⁠
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Des spoke more about his background, how his experiences have shaped his approach to comedy, his connection with the East End, and his WHBPAC show.⁠
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Can you tell us a bit about your background and how you first got into comedy?⁠
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DB: Well, my background is a little complicated, but the quick version is I grew up in Queens, flunked out of St. Francis Prep at 14, and ended up going to Ireland to boarding school in 1990. It was a crazy, life-changing experience, but it definitely saved my education and ultimately inspired a comedy career that in the early days focused a lot on being an outsider looking in. It’s hard to know if I ever would have tried stand-up if I hadn’t been in Ireland. I got sober at 19 and it was a comedian I knew from that world that pushed me to try stand up. Once I got on stage that was all she wrote. I was addicted.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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