Get away from the stresses of work and the hustle and bustle of the city to visit the quaint and quiet town of Shelter Island. Only two hours from the city, Shelter Island is located between Greenport and Sag Harbor, and has been a summer haven for Manhattanites for years. The town has a perfect combination of historical ambiance and relaxed character making it the ideal place to escape to from the concrete jungle we call home.
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I recently took a weekend trip to Shelter Island and was immediately taken back by its quiet beauty. The crisp winter air set the mood for what was to be a wonderful weekend of relaxing and exploring all that Shelter Island has to offer. Upon arriving on the ferry, we went to our hotel: The Shelter Island House. Cozy, chic and classic, this place has it all and was ranked the top Shelter Island hotel on TripAdvisor. The hotel itself was built in the 1800s and is the perfect mix of antique decadence and modern elegance. Its list of amenities is also equally impressive, with great options such as bike rentals, outdoor Petanque courts, a poolside bar and complimentary Wi-Fi throughout the entire property. The rooms range from queen rooms with lofty beds and full bathrooms to its Osprey Suite, a luxurious 3-bedroom suite that can sleep up to 8 people. You can book one of these sophisticated and impeccably decorated rooms for as low as $175 per night.
The island offers up many year-round activities, including countless outdoor options, quaint shops and farm-to-table dining experiences. In addition to its list of things to do, the island is home to the Mashomack Preserve – perfect for hiking and guided nature walks – and four beaches – great for evening strolls especially in the winter months. Crescent Beach is my personal favorite. Feeling adventurous? Every Sunday at noon, a group of locals participate in a polar plunge! Definitely not for the faint of heart. This island definitely has a dream-like quality to it that is guaranteed to rejuvenate and inspire any who visit.
In the evening guests can choose from a variety of restaurants the area has to offer. One of my favorites was The Red Maple, a minimalist restaurant and bar located in the gorgeous Chequit Inn. The diverse menu changes with each season and the restaurant sources most of its ingredients locally, ensuring guests receive the best meals with the freshest ingredients possible. Almost as amazing as its menu is the restaurant’s décor. Surrounded by gorgeous hydrangeas, the terrace has a beautiful Red Maple tree that guests are able to dine under. The outdoor area is especially enchanting, with twinkly lights and a view of the ocean that you don’t want to miss.
We started the night with some cocktails, including a drink called the “Winter Painkiller,” a warm drink made of homemade rum and seasonal spices. There’s truly nothing that shakes off the snow like a warm cocktail. For dinner, it was herb roasted chicken, which was perfectly seasoned and tasty. It came with butternut squash, Swiss chard and black bean hash. Just absolutely delicious!
The next morning, after coffee on the porch, it was off brunch at The Tavern, Shelter Island House’s in-house restaurant, by the roaring fire; it was the perfect end to a wonderful weekend. After leaving Shelter Island, we decided to stop in Sag Harbor for some antiquing and art gallery browsing. Some of my favorite thrift shops in Sag Harbor include Youngblood, Around Again Inc. and .
Shelter Island is a wonderful place to spend your weekend or one day vacation. Whether it be with your significant other or your whole family, there is plenty to do and see. Quiet, historic and warm, this little island could not be any more different than that other island we call home. Whether you go for the day or a full week, you are guaranteed to enjoy great food and beautiful scenery.
For additional information on visiting Shelter Island, visit www.shelterislandchamber.org
By Gwen Wunderlich