Think “winter beach getaway,” and you’re likely thinking of The Maldives, Seychelles, Bermuda, or even Santa Monica, California—not a tiny hamlet on the shores of Long Island. The average high temperature, December through February, is only 44 degrees, after all. Yet, winter holds all the ingredients for a dreamy, laid-back East End getaway.
“The best part about being in the Hamptons in the winter is enjoying the serenity and lack of crowds,” says Tara Poulakis, owner of the Hampton Maid in Hampton Bays. “Enjoy winter walks on the beach, some great hiking trails, check out East End art galleries, and visit wineries on the North Fork.”
Nestled in the town of Southampton, the beauty of Hampton Bays in winter is unmatched. The beaches, usually bustling with summer sun-seekers, are peaceful and scenic, perfect for long walks. The restaurants have little to no waits, the local shops provide an inviting escape from the chilly weather, and the whole area takes on the charming vibe of a movie-like small town.
Initially settled in 1740 as “Good Ground,” this locale was renamed Hampton Bays in 1922. With three bays surrounding the community, Peconic, Shinnecock, and Tiana, it shouldn’t be a surprise that Hampton Bays is the second largest fishing port in New York state, after Montauk.
This is where you venture for an easy weekend getaway or even a weekday day trip (consider this your permission to call in sick). While this is far from an exhaustive guide—48 hours isn’t remotely long enough to check out all of the area’s offerings—here are a few of our favorite, can’t-miss places to get you started.
Breakfasts at the Hampton Maid are legendary. Josh Poulakis creates weekly specials that, in the past, have featured lemon ricotta pancakes, homemade corned beef hash, and an avocado smash. The mainstays, though, are the Hampton Maid Breakfast Platter, a traditional dish featuring all the classics of an American breakfast: pancakes, French toast, eggs, sausage, and bacon, the Eggs Benedict, which on occasion the chef has featured with pork belly or smoked salmon, and the customer favorite Amish Cheddar Omelet—a light and fluffy omelet made with sharp cheddar cheese and served with an herb roasted tomato.
But while the breakfast is renowned, R.Aire restaurant, located just east of the Shinnecock Canal, also serves some of the best dinners in the area. Think a Gamba al Ajillo of sauteed shrimp in garlic and sherry oil, paired with grilled crystal bread, a light, airy bread with a crunchy crust for dipping, DeMarisco Paella, Chef Alex Bujoreanu’s signature Spanish paella that uses bomba rice, calamari, mussels, shrimp and clams, cooked until the socarrat forms on the bottom and the R.AIRE Burger, with a house-ground meat combination of Wagyu beef and chorizo, topped with Manchego cheese and a spicy brava aioli. Did we mention the restaurant is located in one of the most revered hotel restaurants in the Hamptons? • 295 East Montauk Highway; 631.723.2323
This Hampton Bays mainstay is beloved for a reason. Open year-round, seven days a week, Cowfish offers brunch, lunch, dinner, exceptional cocktails, and more—all with stunning, panoramic water views. Menu highlights include the Clam Chowder, deemed by many as the best of the Hamptons, the Thai Curry Cod, featuring local cod, and their truly epic seafood tower. If brunch is more your thing, do yourself a favor and indulge in the Braised Pork Benedict—made with 14-hour BBQ braised pork shoulder, drop biscuit, sauce forestière, roasted mushrooms, caramelized onions, over-easy eggs, and creole mustard hollandaise. It’s winter; your bathing suit will never know. • 258 East Montauk Highway; 631.594.3868
If it’s Sunday, you can’t miss brunch at Edgewater Restaurant. Perched on the edge of the bay, this restaurant pairs stunning waterfront vistas with a delectable menu that includes bottomless mimosas, Aperol spritz, bloody Marys, and rosés. This well-loved eatery specializes in large portions of Italian fare and fresh seafood. You’ll find brunch classics like steak & eggs, avocado toast, and French toast. Want something a little heartier? The lunch menu includes roasted salmon and shrimp pasta.
Not in the area on a Sunday? Edgewater offers dinner Tuesday-Sunday. Take it from us and treat yourself to the lobster pasta—rigatoni, lobster meat, shiitake mushroom, and roasted grape tomatoes with sherry, mascarpone, and a touch of cream. Don’t forget to save room for dessert. We’ll be opting for the almond creme cake, what about you? • 295 East Montauk Highway; 631.723.2323
There’s no reason you can’t have a lobster roll in the winter. To get a top-notch one, though, you’ll need to head off the beaten path to Hampton Watercraft Marina, where Canal Cafe and Market dishes up fresh seafood with views of the Shinnecock Canal. Canal Café is as unassuming as any fish shack. Word of mouth brings most diners here, but this is a local favorite because of its low-key atmosphere, friendly staff and hearty, comfort-driven fare. Weather permitting, you can watch freshly caught fish get cleaned on the deck and offered up on the specials menu. While the menu is seafood-centric, they also make a great jerk chicken sandwich—the perfect bite to heat things up on a cold winter’s day. • 44 Newtown Road; 631.723.2155
Don’t judge a book (restaurant) by its cover. The building that houses Out of the Blue Seafood might be humble, but whether you’re looking to warm up with a cup of clam chowder, eat your way through local seafood with the seafood pasta, or satisfy your craving for steamers, this eatery has a dish for you. You may have to wait for a table, though—yes, even in the off-season. The place is tiny, and the seafood market and restaurant is the type of no-frills place that draws people in with its fresh, local seafood.
The wait is worth it. Go ahead and order up the half-hot and half-cold lobster roll and finally settle the debate of which one you prefer, or for a special treat, try some of their smoked fish. • 252 East Montauk Highway; 631.728.3474
Stepping into Oakland’s Restaurant & Marina feels a bit like showing up for a dinner party at your favorite aunt’s house. The space exudes a welcoming atmosphere with just enough upscale chic to make it feel festive, but not intimidating. It’s no wonder the restaurant has been a favorite for 30-odd years.
It’s all about the view at Oakland’s Restaurant & Marina, located at the very end of Dune Road. Try to time your visit with the sunset and snag a table by the water. The views never fail to disappoint. Nor does the food. The seafood is, of course, top-notch. You’ll find tender, local sea scallops, crab cakes that are big enough to share, and clam chowder you’ll rave about for years. One of the best things about this restaurant, though, is the diversity of the menu Executive Chef Corrie Dietrich has put together, featuring a range of meticulously crafted dishes that cater to various tastes and preferences. From gourmet burgers and succulent steaks to inventive salads and pasta options, there’s something here for everyone. • 373 Dune Road; 631.728.6900
It’s ‘island time’ all the time at this epic, waterside restaurant and rum bar. Located on the Shinnecock Bay, RUMBA offers Island-inspired cuisine, excellent rum-based cocktails, and reggae music all year long. It is, as the kids might say, a vibe. It is also the perfect place to visit if you’re craving more than a staycation; RUMBA delivers all of the flavor of a Caribbean vacation without the travel or flight.
Whatever your tastes, there truly is something for everyone here—from Dominican Ribs, served with a sweet chili ginger soy glaze, fresh herbs, mashed sweet potatoes, and pistachios, to Soy and Sugar Cane Salmon, served with coconut risotto and a vegetable of the day. Wash it all down with a classic daiquiri and you’ll swear you’ve died and gone straight to the Bahamas. • 43 Canoe Place Road; 631.594.3544
The new kid on the block, Fins and Forks, is a casual spot ideal for a relaxed lunch or dinner. With coastal-inspired décor and a laid-back atmosphere, you’ll feel transported to a beachside retreat no matter the weather outside. It’s the type of place every neighborhood should have with gorgeous, delicious, and cooked-to-perfection food and a friendly vibe. While the restaurant hasn’t been open long, a few favorite dishes so far are the fried calamari, which is incredibly tender, oysters, and mahi mahi tacos. Don’t worry, though; this isn’t just a seafood spot. The chicken wings are also a must, and we’ve heard good things about the desserts, especially the key lime pie. Pro tip: check out their Instagram (@finsandforks.hamptonbays) before you go to see if you want to visit on a particular night for live music, bingo, or another one of their events. • 78 Foster Avenue; 631.594.2980
Pro tip: bring a cooler with you to Hampton Bays. On your way out of the hamlet, you’ll want to stop by this seafood lover’s paradise, Lighthouse Seafood. It’s a local favorite for its selection of fresh and locally sourced fish and shellfish—the selection is varied and more extensive than most supermarkets—and after a day or two of dining on incredible seafood during your Hampton Bays getaway, you’re going to want to grab some items to go. Not sure what to get? The staff at Lighthouse Seafood are really the best part of this place. They’re always knowledgeable and generous with cooking tips and recommendations, especially when you want to broaden your seafood favorites. For some fish, they will even offer to make the portion cut to your specifications. You’ll also find several ready-to-eat and made-to-order items if you need a sandwich or a salad for the road. • 36 Lighthouse Road; 631.728.5186
Where to Stay & What to Do When You’re Not Eating
Make your base the Canoe Place Inn or the Hampton Maid (home to R. Aire). The Canoe Place Inn is a historic gem. Dating back to the early 20th century, the iconic property has been meticulously restored. You’ll find it situated along the shores of Shinnecock Bay, offering stunning waterfront views and easy access to the beach. Inside, you’ll find luxurious, cozy guest rooms and suites to rest your head. Not far away, the family-owned and operated Hampton Maid is equally charming and has been a destination since 1959.
Tucked into a quiet hillside, it’s not walkable to the beach, but the hotel features individual cottage-style rooms, acres of lawn for the kiddos to run around in, and owners and staff that make you feel like part of the family.
When you’re not eating and drinking, pop in and out of the shops, searching for treasures at famed antique stores Good Ground Antiques and James Maguire Antiques or used bookstore Twice Sold Tales. Meander the long stretch of Ponquogue Beach (even if there is snow on it) and take a drive to some other East End favorite hamlets like quirky Amagansett.
This dreamy beach getaway isn’t one you’ll forget anytime soon.