By Amanda Feldman Jay

A summer playground for the Tristate area elite, The Hamptons is best known as a coveted seasonal destination, highly trafficked between Memorial Day and Labor Day. And while it’s true there is something magical about these pristine beach towns in-season, The Hamptons in the off-season is the best kept secret. Amagansett in particular is a charming little hamlet wedged between East Hampton and Montauk with a less flashy vibe than its neighbors to the east and west. In its seasonal prime, the beaches and shops are ripe with weekenders and vacationers galore, so when the crowds are gone you have the opportunity to appreciate just how magnificent this slice of bucolic bliss is without any distractions. Plus, you can score stress-free access to some of the best spots in town without having to book months in advance or pay premium prices. Escape the March madness and homebound monotony with a winter visit out east before the warm weather throngs flock back.

If serenity is what you’re after, look no further than The Roundtree, Amagansett, a new boutique hotel that made its grand debut in summer 2020. This 15-room pastoral gem comprises a historic barn and cottages that have been restored to modern Cottagecore perfection and could be easily mistaken for a generous friend’s country estate. Surrounded by idyllic farmland and white sand beaches, The Roundtree is located on Main Street, a mere few steps away from the stylish boutiques and gourmet eateries of Amagansett Square.

Equal parts cozy and luxurious, The Roundtree is an elegant, minimalist oasis anchored by a calming neutral palette throughout. Each guest room, suite, and cottage is outfitted with thoughtful amenities to evoke the comforts of home including Frette linens, Matouk towels, Grown Alchemist bath products, and hand crafted Kevala ceramics. Be warned, you may check out feeling inspired to upgrade your own home amenities following your stay. Luckily, The Roundtree Boutique in the Main House carries all the goods you’re bound to wish were yours after indulging in them during your stay.

Perfect for a romantic retreat, a low-key getaway with friends, or a full family affair, The Roundtree is uniquely child- and pet-friendly. The myriad of accommodation options makes for seamless planning of whichever kind of escape you’re seeking. My fellow dog parents whose canine children weigh more than 15 pounds are likely familiar with the struggle to find luxury hotels that welcome our furry family members. If you count yourself in this camp, consider this reason enough to add The Roundtree to your list of must-book properties. Your pup will be welcomed with open arms and treated to luxury amenities of their own including a plush dog bed and a yummy welcome treat.

If you need an excuse to linger in bed longer in the mornings, you’ll appreciate the hotel’s complimentary continental breakfast service delivered right to your door, including your choice of morning beverages and light bites to get the day started. And upon return to your Hamptons home-away-from-home after a brisk afternoon out and about, you can warm up to a cup of tea and freshly baked cookies, which are seemingly restocked round the clock and ready for the taking. These midday pick-me-ups are available in the Main House’s kitchenette and accessible to all in-house guests complimentary. Other delicious, winterized offerings include nightly s’mores outings by the fire-pit as well as a bookable Fine Dining Reimagined experience, which is perfect for keeping safe and warm during this final stretch of winter. A delectable feast will be freshly prepared and delivered by one of The Roundtree’s local restaurant partners and expertly served in courses by the property’s hospitable staff. You choose the setting – either the privacy of your room or your own reserved space by the fireplace in the Main House.

Wölffer Kitchen, the bohemian eatery and first winery-owned restaurant on the East End, offers year-round dining via creative takes on local and seasonal cuisine. A concept from Wölffer Estate Vineyard, the menu reflects seafood-forward starters, salads, pizzas, and hearty mains that naturally pair superbly with Wölffer’s robust collection of locally made wines, ciders, and spirits. Take note of which bottles you like best and be sure to stop by Wölffer’s drive-through wine stand to bring your favorites back home.

For organic coffee and vegan baked goods on the go, Jack’s Stir Brew Coffee is simply the best. This New York City coffeehouse turned local chain has seven locations in the NY area and is an unmissable Amagansett staple.

Take a short drive several miles east to enjoy lunch or dinner at Sel Rrose Montauk, a chic Parisian-inspired oyster bar with swoon-worthy interiors and equally enticing menus. Pro tip: order the catch of the day, which is caught fresh each morning right in town by local fishermen.

If you’re up for a scenic drive, head up to the North Fork, just across the bay, for a visit to Long Island’s wine country. Macari Vineyards in Mattituck has individual vineside bungalows with fully winterized setups in glamping tents as well as a tasting room and heated patio. Bonus: pups are permitted in both the indoor and outdoor spaces at Macari. The charming One Woman Winery in Southold produces certified sustainable wines from entirely estate grown grapes by vintner extraordinaire Claudia Purita. Support this woman owned local business by enjoying a bottle onsite by the firepit or grabbing some vino to go.

Bundle up and take a peaceful stroll along the beach. The meditative sounds of the ocean and beauty of an empty shoreline is akin to magic and an off-season rarity to be cherished. If you’re feeling up to spending more time outdoors, there is an endless selection of hiking and nature trails nearby.

Swing by the Parrish Art Museum to catch the Field of Dreams outdoor exhibition, the museum’s inaugural sculpture display. While the museum’s indoor spaces are closed until later this spring, the outdoor exhibit was created to extend the museum’s collection into the surrounding meadows with work that engages and responds to the Parrish’s architecture and landscape. The exhibit is free and open to the public daily.

Photo Credits:
Alex Ferrone
Discover Long Island
Montauk Chamber of Commerce
The Roundtree