Growing up in New York, I can count a number of times I visited the Hamptons. Let’s see. Once. Yes, only once. I have always wanted to go back because of the beauty of this part of Long Island. The expansive shorelines and the immaculate buildings contribute to the lively Summer months when the city is awash with tourists.
When the cold comes, as it inevitably does, you will find that this part of Long Island becomes very ghostly. The families pack up, and return home to school and work, while the travelers move on to warmer waters.
Despite the solitude, there is still plenty to see and do during this time of year, and the beauty of the Fall can be peaceful and calming. Experience the leaves changing colors, setting the forest ablaze with brilliant reds, yellows, and oranges. If you are planning a trip to the Hamptons during this season, you will have to visit the beaches. Unlike Summer, the beaches during the Fall are desolate and serene. Stroll across the sand, while the salty air whips your scarf and sweater.

New York is notorious for its delicious apples, which ripen as the leaves begin to turn. Head over to one of three apple orchards, to enjoy the farm experience. At the orchard, you can browse the farmer's markets for the best apple cider, pies, and other fresh fares. The kids will particularly enjoy the rides on the tractor and the corn mazes. Take the long trip out to the Hudson Valley, for more expansive farms, set in the bountiful hills.
While pumpkin spice everything is in town, a lot of the breweries have adapted their own spin on pumpkin-based beers. Why not try it? The Greenport Harbor Brewing Company as a delicious selection of artisan beers, all made on Long Island. Try also the popular husband and wife-owned brewery, Moustache Brewing Co, which opened its doors in 2014. This part of Long Island is known for wine and beer of excellent quality. There are tons of wineries that are accepting walk-ins for wine tastings. Mere minutes outside of the Hamptons is the Martha Clara Winery. I was taken here during my bridal shower, and I have to say it is one of my favorite wineries on Long Island.
Head into the village of Montauk, to experience this nostalgic fishing village- turned tourist hub. To avoid the crowds, try visiting Montauk in the winter. Surfing at Ditch Plains Beach, you can catch the incredible winter swells, before the temperatures turn to harsh. Embrace the natural landscape at Montauk Point State Park, a forest of wind-whipped trees and excellent ocean views. Don't miss the famous lighthouse, perched on the outer-most point of the park.
Relish the flavorful dishes and enticing atmosphere at the Gig Shack. This family-operated restaurant is a popular eatery for locals and tourists alike. They serve local, surf-style food, but with an international flair. The lobster rolls, in particular, are a must-try. Sit back, sip the Gig Shack's own Montauk Hard Label beer, and enjoy a live music performance.
School is in session, and families have gone home, it is the best time of year for a quiet getaway to the Hamptons. Fall and winter in Long Island will reveal a completely unique holiday experience. Tranquil shores and friendly locals contribute to a truly restorative experience.
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