Uncovering the Art of Memorial Day Weekend: Tips to Beat the Chaos Without Compromising on Fun

As Memorial Day Weekend approaches, it's time to get excited for summer in the Hamptons! While everyone looks forward to the long weekend for relaxation and fun, it can quickly become chaotic as thousands of people flock to the same spots which often results in traffic jams, overcrowded restaurants, and lines for coffee that seem never-ending. Despite these challenges, you don't have to compromise on a memorable and enjoyable weekend! In this blog post we are providing tips on how to make the most out of your Memorial Day Weekend in the Hamptons so you can enjoy yourself without all the stress.

If you want to make the most of Memorial Day Weekend in the Hamptons, it's best to leave New York City on Friday morning. Leaving on Thursday is even better if possible! This will give you a headstart and allow you to avoid traffic jams across Long Island. You have to remember this is the first big check-in weekend for summer renters. Everyone wants to get out and get settled for a summer of fun. In previous years, we've heard of people leaving Friday afternoon and getting stuck in traffic for 7 hours. If you can't leave early, then just wait til Saturday morning and drive out early.

Next we just recommend having your expectations in check. It is going to be busy. Don’t go anywhere if you’re extremely hungry or wanting something in a timely manner. Just mentally being prepared for long waits can completely change your experience. We recommend keeping essentials at your house like cold brew and breakfast—maybe some rosé. Just make life easy for yourself and only fight the crowds for something you really want or need. If you’re planning on grocery delivery, schedule it now.

Unless your one dream in life is to be at the Surf Lodge on Memorial Day Weekend, we just recommend avoiding all The Hamptons hot spots. That doesn't mean you stay holed up inside all weekend, but plan to go to one or two of your favorite spots and if the lines are unbearable, have a back up plan.

Weather for Memorial Day Weekend is always a little spotty. It can be beautiful one day and cold and rainy the next day. Remember it is always slightly colder on the East End than in the city. If you have a rainy day, plan for shops and movie theaters to be slammed. Be prepared with appropriate clothing and shoes.

Even though shops will be packed, it is often a really fun weekend to be in town. Lots of stores have fun pop ups happening or are serving treats like champagne or desserts. This usually happens earlier in the day so plan to shop when shops first open around 10am.

Memorial Day Weekend is also known for parties and BBQs. Throwing a party or attending one is a great way to avoid crowds and still have a ton of Hamptons style fun.

And if you want to know our plan—

We’re going to do Montauk on Friday but stick to low key places like Topside at Gosmans for drinks and dinner at Westlake Fish House where we don’t mind if we have to wait for a table. Saturday we’ll be checking all of you into your houses but might brave the crowds for a sunset drink in our neighborhood at Sunset Harbor or Bostwicks on the Harbor… and Sunday we have a few parties we’re going to tackle back to back. Any other free time, we’ll get to the beach if weather permits!

Good luck out there! And remember to just relax without crazy expectations for the best weekend of your life. Oh and be super nice & tip any one working over the weekend.