5 Reasons to Visit the Hamptons Year-Round

The many and various pleasures of the Hamptons scene in the summer are no secret. Anyone who’s taken the Long Island Expressway on a Friday afternoon in the summer knows that the Hamptons are a magnet for many.

Hop on a Hampton Jitney bus or LIRR train and you’ll find yourself crammed in with young, beautiful people (many still in their business attire), armed with their iPads, overnight bags and hopeful expressions, all eager to get to the pristine beaches, the farmstands, and the vibrant nightlife.

In the early 2000’s, people started coming to the Hamptons well beyond the summer season. However, the financial crisis of 2008 caused the season to revert to a three-month Memorial Day to Labor Day window of time. Which is a shame, because the area is beautiful to visit in spring and autumn.

Some argue that it’s even more appealing in the off-season because the crowds are absent and the restaurants are glad to see you. Also, don’t discount the advantages of being able to park without risking a heated encounter with another frustrated driver. Or being able to drive from Southampton to Montauk on Route 27 without resorting to the convoluted map of the back roads because traffic is bumper-to-bumper.

So here are some of my favorite things to do both during the summer season and before/after:

A Boat Ride from Sag Harbor to Ram’s Head Inn, Shelter Island

If you’re lucky enough to own a boat or, second best, have an obliging friend who owns a boat, taking a ride from Sag Harbor to the dock of the Ram’s Head Inn is a summer treat. Being out on the water is refreshing and exhilarating, even for this short ride.

There’s the different perspective afforded by looking back from the water towards the town. And there’s the feeling of being part of a summer fantasy of beautiful people doing glamorous things without the bother of wearing jewellery or high heels (although you can if you want to).

Upon arrival at the dock, walk up the broad lawn towards the verandah of the hotel, and have lunch or dinner at the tables set with flowers and candles. The food is smashing, and the view from the verandah seems more Newport or Nantucket than the Hamptons. Sigh…

The Longhouse Reserve, East Hampton

This 12-acre property is owned by Jack Lenore Larson – a big-name textile designer back in the day – who built himself a Japanese-style long house on the property along with a large and lovely lily pond. The grounds are covered in an extraordinary range of exotic trees and flowers that reflect the changing seasons – a big favorite is the Red Garden which comes into bloom sometime in May and features trees, flowers and antique statuary in varying shades of red. The entrance to the property features a large Chinese bell with a wooden mallet that you can bang away with to let the world know you have arrived.

The grounds include some perennial art works such as a deKooning sculpture, a non-competitive Yoko Ono chess set (you have to see it to understand, which is typical Y-O) and each year a new influx of works from artists from around the world but with a focus on the oriental. My favorite treat is to visit during the week when there are fewer visitors and plonk myself down under a tree on an ancient carved bench with a really good book – bliss!!!

The Beach

Yes, I know – hardly a revelation!! But I’m not talking about the summer beach which, to my mind, is overheated in more than one sense – crowded, noisy, hot and always makes me think of the movie “Suddenly Last Summer.” The summer beach is all about the people on the beach – not that there’s anything wrong with that! But I am talking about the beach in late September through April, when the people are mostly gone, and when long, solitary walks have only the sound track of birds, waves and your own heavy breathing.

The off-season beach is about the beach, not about the people on it, although you may run into a few determined joggers and the occasional muffled-up dog walker. The off-season beach is about the breathtaking glory of sunrise and sunset, uninterrupted by distractions; the smell of the ocean; the cold winter sun blazing off the ice-coated beach grass, turning it into a field of Swarovski crystals any diva would lust for. The off-season beach is mystical, especially on a foggy day when people silently appear and disappear in the mist.

The summer beach makes people think about tanning and what’s for lunch and who is that cute guy/gal over there. The off-season beach makes you think about the bigger existential questions – who am I and why am I here… That’s my beach!

Villa Italian Specialties, East Hampton

At first glance, this looks much like any other Italian deli with its trays of artichoke hearts, peppers, racks of pasta and olive oils, etc. But the nectar of the gods lies in the sandwiches prepared on warm focaccia, filled with fresh grilled chicken, pesto, peppers, home-made mozzarella and some kind of secret dressing that is orgasmically delicious.

Based on the premise that all delicious things are either immoral, illegal or fattening, I have to assume these sandwiches can inflict some kind of irreparable harm on those who consume them, but they are too good for that to matter. “Life is short,” I justify to myself as I sink my teeth in.

The best treat of all is to eat one of these sandwiches at the beach, and then walk it off. Or, on an escalating scale of happiness, you can share the sandwich (and some of the guilt and avoirdupois) with a loving friend and then walk on the beach hand in hand. The ‘Villa Tiramisu’ is pretty fab too, but that’s only for when I feel completely reckless about my waistline and my arteries.

The Lighthouse Swing

Yes, everyone knows about the lighthouse at Montauk and it is a wonder to behold. But if you search down one of the paths that wind from the lighthouse to the beach you may find a wide wooden swing (big enough for two) that positively demands you leave your adult self behind and kick your heels up in the air while gazing at the ocean that stretches away to the good old UK and our former colonial rulers.

So, what are you waiting for? Share your own Hamptons favorites with us below, in the comments!