Just like anything, beauty is in the eye of the beholder. This is even more true when planning a trip to The Hamptons. There are many different sides to The Hamptons and each person tends to have their own preference.
If you want to experience The Hamptons that you read about & watch on TV
Your best bet is to visit during peak weekends. (Think Memorial Day, 4th of July, and Labor Day). This is when venues are throwing parties, beaches are buzzing and you will meet others here just for the weekend as well.
If you want to experience the natural beauty, good restaurants, and shopping, but really would prefer to avoid the crowds and traffic
Try for June. Everything is open for the season but a lot of seasonal renters have not fully moved out because of schools still being in session.
If you want to see The Hamptons like a local, you'll want to go in the spring or fall.
A lot of seasonal businesses may be closed, but enough are open to make the experience fun and memorable. You won't be sun bathing on the beach, but you'll definitely be able to take a beach walk or catch a beautiful sunset.
Plus hotel & rental prices are a bit more reasonable.
And to experience a totally different & magical side of The Hamptons, visit in December
Yes it will be cold (it is NY after all), but all of the villages are dressed up for the holidays and you will experience a cozy side to life by the sea. Find a hotel or restaurant with a fireplace or fire pit and cozy up with a cocktail.