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Hamptons.com
February 11, 2022

Sixty-Something: Five Historical Romantic Locations in the Hamptons

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

With Valentine’s Day just around the corner, I could not help but think about romance because I believe it is the magic of life. The Hamptons is filled with beautiful vistas. It has many beaches, trails, lighthouses, and old country farm roads. It was easy to pick five romantic spots to write about because there are countless such locations. So, I picked my five favorites.

 

First, since I lived in Montauk the longest of my bachelor east end years I nominate Camp Hero, in Montauk. Specifically, the trail heading from the parking lot east toward the bluffs overlooking the Montauk Lighthouse. I have stood there for sunrises, moonrises, clear-night stargazing, not to mention midday ocean viewing. It’s a great romantic spot. Best to go there on off hours so you can be alone. For anyone wondering, Camp Hero is named for General Andrew Hero who was the U.S. Army’s “Chief of Coastal Artillery,” in the 1920s. The camp was named for him after his death in 1942. He was born in Louisiana. He never actually saw the bluffs and lighthouse of Camp Hero.

 

Then, there is what I will group together as the Gerard Drive-Louse Point zone in the Springs. A favorite of locals who often bring a few chairs, a bottle of wine and then watch the sun set during the season. Perfect for scenic walks and especially stargazing. I used to have a VW convertible and would stop on the narrowest stretch of Gerard Drive where there is a small bridge. Sitting on the top of the seats with the top down I would search the night skies for shooting stars and perhaps some romance. Note: Until 1926, Louse Point Road was called Dog’s Hole Highway. Local property owners successfully petitioned the town to change the name. The tip, known as Louse Point, has its own story. Legend has it the original settlers called it that because, “it was so barren it wouldn’t support even a louse!”

 

A similar type of experience can also be had on Ram Island Drive on Shelter Island. I believe in the off season it is the ultimate place for stargazing, with the road slicing through Coecles Harbor and Gardiner’s Bay with a priceless view of Bug Lighthouse. At one spot both the harbor and the bay are less than ten feet from the road. Under a full sky of stars, in the off season, this place is as romantic as it gets anywhere on earth. The road was built to connect Little Ram Island and Big Ram Island to Shelter Island.

 

The next spot is a combination of every Hamptons Ocean Beach location. If one walks a hundred yards or so east or west, you are basically alone. Looking at the stars and listening to the cadence of the ocean’s waves breaking on the shore is special. There is always a strong magical feeling of romance when you are on an ocean beach after hours. My favorite beach for romance is Ditch Plains. The bluffs, the rocks, give it a unique un-Hamptons beach feeling. A popular beach with surfers, there may be others feeling romance at this location at any time all year ’round.

 

Finally, there is Conscience Point, Southampton. This is the location of the landings of the original settlers in 1640. The spot is easy to drive to, just off North Sea Road. It has a short, wonderful shell covered trail to the big rock with a plaque on the water’s edge. The bronze plaque states that this is the actual designated area where the folks from Lynn, Massachusetts, then a colony of England for only 20 years, stepped ashore to establish the Hamptons. It was a June day, and the area was surrounded by Shinnecock Indians who lived around the harbor. When there you can literally feel the spirits of the folks who inhabited that area for perhaps a few thousand years. It is a very romantic spot. The stillness is blissful.

 

Yes, there are so many romantic locations in the Hamptons. For many it has been a tough two years of fear and isolation. Hopefully, the darkest hours of the pandemic are in the rear-view mirror. This Valentine Day, get a card, get some flowers, do something romantic. The older you get, the more you realize how powerful love is.

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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.⁠
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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.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptons #saunders #community #foodpantries
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