Fall Is the Best Time to Visit the Hamptons: Where to Eat With an Ocean View in Montauk

The Hamptons is a quintessential fall weekend trip that has it all: fall foliage, apple picking, pumpkin hunting, outdoor drinking and dining options that can satisfy families, couples and individuals alike. The enclave at the east end of New York’s Long Island peninsula hosts chaotic summer crowds, but things slow down considerably in early fall, making it the best time to visit this Hamptons hub. The exclusive beach town of Montauk, New York, has transformed into one of the hottest summertime escapes on the East Coast.

The crowds are gone, the weather is still nice, you can actually get dinner reservations and the hotel rates are much more affordable. And you’ll have plenty of room to spread your towels on popular beaches such as Ditch Plains and admire the surfers who prefer to avoid the busy summer months. An easy journey from New York City, the Hamptons are accessible via bus, car and train. Flying out to Montauk is definitely the fastest way to get there. BLADE offers regularly scheduled flights to South Hampton, East Hampton and Montauk. You can choose to buy a seat on a scheduled flight or charter a private flight.

1. Where to Eat With an Ocean View in Montauk

Scarpetta Beach, the seaside sister of the iconic Manhattan eatery, is open nightly year-round and serves up soulful Italian food in addition to seasonal dishes, fresh seafood selections and a world class beverage program. The restaurant’s name is derived from the Italian expression, “fare la scarpetta,” which means to savor a meal to the very last bite.

The design combines mid-century modern aesthetics with the seaside, both in the dining room and the outdoor deck which has a panoramic view of the ocean. Scarpetta Beach’s beverage program is unparalleled with an Italian spin on classic cocktails and a world-class wine list. While taking in the salty air and sound of the waves, you can enjoy the below fan-favorite dishes and cocktails.

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Scarpetta Beach’s beverage program is unparalleled with an Italian spin on classic cocktails and a world-class wine list. Sip on the Margarita Italiana with Casamigos blanco tequila, Aperol, Cointreau, agave nectar, and fresh-squeezed lime juice or Charli's Gone Surfing with Bacardi 8 rum, plum liqueur, Demerara syrup, and fresh-squeezed lime juice.

Favorite seafood classics include Diver Scallop with preserved truffle, lemon, Aleppo and pea purée, Lobster Tagliolini Nero with lobster, tomato and spiced basil breadcrumbs and Black Cod with caramelized fennel and concentrated tomato.

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2. Explore Vineyards and Wineries

The Hamptons are home to several wineries and vineyards. Enjoy wine tasting, tour the facilities, and take in the scenic landscapes as the leaves change colors. Wölffer Estate Vineyard is a renowned winery located in the Hamptons. It's a popular destination for both locals and visitors seeking a unique wine experience. The estate is set against a picturesque backdrop of vineyards, rolling hills, and open spaces. The beauty of the landscape makes Wölffer Estate a perfect spot for leisurely walks and relaxation, and offers guided tours of their vineyards and winemaking facilities. You'll get insights into the winemaking process, learn about the history of the estate, and gain a better understanding of the local terroir.

Source: Wölffer Estate Vineyard

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The tasting room at Wölffer Estate Vineyard is a beautiful and inviting space where you can savor your wine samples. There's also a lovely patio area where you can enjoy the stunning vineyard views while sipping your wine. And last, but not least, the vineyard offers a variety of wine tasting experiences. You can sample a range of their wines, which include a selection of reds, whites, and rosés. Their signature rosé wines are particularly well-known and highly regarded.

3. Enjoy Nature Walks and Hikes

Fall is an excellent time for outdoor activities. Explore the area's natural beauty by taking hikes in spots like Hither Hills State Park, the "Walking Dunes" trail is a popular choice, or exploring the trails at the Elizabeth A. Morton National Wildlife Refuge. This refuge in Sag Harbor offers a short, scenic loop trail that takes you through a variety of habitats, including woodlands, grasslands, and salt marshes. It's a great spot for birding and observing wildlife. Paumanok Path is a long-distance hiking trail that stretches across the entire length of Long Island, including sections through the Hamptons. You can choose shorter segments for day hikes or longer portions for a more challenging trek.

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Located in Montauk, Shadmoor State Park features a short loop trail that leads to elevated bluffs overlooking the ocean. The views are spectacular, and the park also has historical significance. In East Hampton, Cedar Point County Park features several trails that take you through woodlands and salt marshes. The trails provide opportunities for birdwatching and enjoying the waterfront views.

4. Relax on Less Crowded Beaches

While the water might be too chilly for swimming, the beaches are less crowded during the fall. Enjoy the tranquility and take a leisurely stroll along the shore. Take leisurely walks along the shoreline, enjoying the crisp air and the sound of the waves. The fall foliage can add a beautiful touch to the coastal landscape. The softer lighting and changing colors of fall can provide excellent opportunities for photography. Capture the scenic beauty and capture the quieter, more serene atmosphere. Some Hampton’s beaches allow dogs during the off-season. If you have a furry friend, this can be a great opportunity for them to enjoy the beach as well.

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Pack a picnic and enjoy a meal by the water. Beachcombing for shells, driftwood, and other natural treasures can be a peaceful and rewarding activity. Fall often brings stunning sunsets. Bring a blanket or a beach chair and watch the sun set over the ocean. The colors in the sky can be particularly vibrant during this time of year. Check local regulations and guidelines, but some Hamptons beaches might allow for beach bonfires during the fall. It's a wonderful way to stay warm and create a cozy atmosphere as the sun sets.

5. Experience Hamptons Art and Culture

The Hamptons have a thriving arts and cultural scene. Visit local galleries, art studios, and cultural centers to experience the creativity of the area's residents. Around Halloween, you’ll find haunted houses, pumpkin carving contests and other spooky-themed activities. Become a paranormal investigator at the Southampton Museum. The Southampton Museum’s Haunted Village brings ghosts, goblins, and ghouls to the grounds of Rogers Mansion.

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With live music, talented DJs, and the best costumes on Long Island, The Clubhouse Hamptons’ Halloween Party is a can’t miss event. Featuring spooky cocktails and a costume contest, this annual celebration is a local favorite event, with hundreds of guests dancing well beyond the witching hour every year.

6. Visit Local Farms and Orchards

Fall is the perfect time for apple and pumpkin picking in the Hamptons. Many farms in the area offer these activities, along with hayrides and corn mazes. Located in Water Mill, Hank's Pumpkintown offers a range of fall activities including pumpkin picking, corn mazes, hayrides, and a playground. They also have a market with fresh produce, baked goods, and more. Situated in Water Mill, Milk Pail Farm is known for its apple orchards and offers apple picking during the fall season. They also have a farm market with fresh produce, pies, and other treats.

Source: Hank's Pumpkintown

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Found in Water Mill, Seven Ponds Orchard is a family-owned orchard where you can pick apples, pumpkins, and other seasonal produce. They also have a market offering homemade pies, cider, and local products. Located in Cutchogue, a bit farther east on the North Fork, Wickham's Fruit Farm is one of the oldest working farms in the area. They offer apple and peach picking, as well as a farm stand with various fruits, baked goods, and preserves.

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