Whalebone Magazine

The Offseason

Everything in life is relative, and seasonality on the East End is no different. Seasons are divisions in the year, which are characterized by amount of daylight, as well as changes in weather and ecology. These changes are caused by the tilt in the earth’s axis, exposing different regions of the globe to more or less sunlight. Scientifically there are four seasons in Montauk, but culturally there are two, the Season and Offseason.

Most of you reading this enjoy Montauk during the Season. You wake up to beautiful weather; grab a cup of coffee and a bite to eat at your favorite spot. Next you wonder down to the beach with your chair and umbrella, work on your fabulous summer tan, maybe go for a surf or swim. Later in the evening you are enjoying cocktails at a sunset view bar. Waiting for your reservation at your favorite restaurant, where you will enjoy incredible food and a good bottle of wine. Tomorrow you will repeat this schedule with slight variation; it is all a dream.

Photo: Grant Monahan

For most local residents and me, who have seasonal jobs, the Season is filled with work, a lot of hard work. The Season is even tough on those local residents who work year round jobs. It is crowded; trying to go out to dinner is almost impossible, the grocery store becomes a gauntlet, and your favorite stretch of white sand becomes a techno-colored sea of umbrellas and blankets. I personally put my head down, work 7 days a week for 12 plus hours a day, and keep my eyes on the prize, Offseason.

For me Offseason starts October first and ends about mid April, when my sister and I have to start getting the business prepped for the Season approaching. The start of Offseason is incredible, the weather and water are still warm, most restaurants and businesses are still open, and you have free time, so much free time! You fish, surf, enjoy happy hour, and see the whole community of Montauk with smiles on their faces.

Photo: Grant Monahan

Photo: Grant Monahan

My favorite local watering hole closes mid-November, a sign that the middle of Offseason is upon us. The days get very short, the temperatures drop, and the weather gets nasty. Montauk becomes a very lonely and desolate place during this time of year, but the beauty never leaves. Imagine Ditch Plains empty, not a soul in site, the entire beach is sparkling white, the cliffs are patched with snow; it is mesmerizing. There are still some restaurants and bars that stay open allowing you to battle these cold months with friends and alcoholic beverages.

Over time the weather begins to warm up, people start to return to town, and businesses and restaurants reopen their doors, making you realize how much you actually missed them. The Season is quickly approaching and we pack all of our fun in to these last couple weeks. Enjoy it because soon you will only know work.

Even though Offseason is such a glorious and beautiful time in Montauk it is best spent on vacation, away from the elements. Somewhere warm and tropical where you wake up to beautiful weather; grab a cup of coffee and a bite to eat at your favorite spot. Next you wonder down to the beach with your chair and umbrella, work on your fabulous vacation tan, maybe go for a surf or swim. Later in the evening you are enjoying cocktails at a sunset view bar. Waiting for your reservation at your favorite restaurant, where you will enjoy incredible food and a good bottle of wine. Tomorrow you will repeat this schedule with slight variation; it is all a dream.

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