8 Reasons to Visit the Hamptons and North Fork This Fall

Cheaper hotels, no crowds and fall pumpkin picking
May 18, 2015
by Sara Ventiera

Between traffic jams and overstuffed restaurants and bars, the Hamptons can be a hectic travel destination during the summer months. But post–Labor Day weekend, the East End "see-and-be-scene" chills out and the farms and wineries heat up. From big discounts on trendy hotels to tables at the hottest restaurants in town, here are eight reasons to visit the East End this fall.

It’s Easier to Get Into the Hot New Restaurants

This past summer, it took 30 days to get a reservation for the newly opened Scarpetta Beach at the new Gurney's Resort & Seawater Spa in Montauk. Without a booking, waits for outdoor tables could easily hit the 90-minute mark. Momi Ramen, the East Hampton location of Miami’s favorite housemade noodle joint, was packed since opening in June (despite the 80-degree temps). Winston’s Bar & Grill, the casual Caribbean-infused eatery opened by Jamaica-native and longtime East End chef Winston Lyons, rarely offered a weekend table without a wait. Now, all these fresh new eateries have plenty of room, minus the over-the-top summer scene.

Fall Wine Crawl on the North Fork

Autumn is when all the harvest action goes down at East End wineries. Right now, grape-growers are pulling the fruit off the vine and starting the hands-on portion of winemaking process. So now's the time to watch the magic happen. In Mattituck, Macari Vineyards, 2014 New York Wine & Food Classic’s “Winery of the Year” award-winner is open seven days a week as well as its Cutchogue location. Martha Clara, in Riverhead, is also accepting tasters daily, and on weekends, expect an array of arts and music events. Watch the sunset over the sound at Kontokosta Winery in Greenport. On Friday and Saturday nights, the winery serves wine by the glass in the tasting room and on tables set outside right on the bluff with prime views.

Montauk Is Actually Manageable

A one time blue-collar beach town, Montauk has been swarmed by the summertime scenester crowds. This year the parties were so big, the village called emergency meetings to figure out how to quell the madness. The Crow’s Nest, The Surf Lodge, and Ruschmeyer's are closed for the season, but there are other places still catering to fall's more laid-back visitors. Classier than some of the other party places in town, Navy Beach is set on a private beach with nautical decor and upscale coastal cuisine. It’s still open through mid-October without the any of the amateur crowds.

With some of the freshest seafood (the docks are right next door) and best sunset views, Inlet Seafood sees multihour waits in season. It’s much easier to handle now. The scenic eatery is open on weekends through Thanksgiving.

Fall Farm Stands

Summer tomatoes and berries are gone, but East End farms stands are still full of fresh produce. On Saturdays and Sundays, Hank's Pumpkintown in Water Mill offers apple picking, pumpkin patches, roasted corn, fresh pies, cider donuts, wagon rides, a maze park and more. Down the road, the Milk Pail opens its orchards and pumpkin patch for those looking to get up close and personal with the fall bounty in its natural surrounds. Pick Golden Delicious and Empire apples straight off the trees while gourds, acorn and delicata squash can be pulled right off the vines, Friday through Sunday. Both are the perfect setting for those obligatory fall pumpkin-patch photos. For the best pies on the island, head to Riverhead's Briermere Farms. Golden crusts are full of tree-ripe apples and fruit.

Trendy Hotels on the Cheap

Once the Labor Day crowds subside, so do the sky-high hotel prices. Trendy Hotels like Sag Harbor’s Baron’s Cove, the newly renovated Gurney’s Resort & Seawater Spa in Montauk and Bridgehampton’s Topping Rose House drop prices by 50% or more. That leaves more cash in hand for wining and dining at the on-site restaurants. This year, Gurney’s got a complete food and beverage redesign with help from LDV Hospitality Group (American Cut, Barchetta), including the acclaimed Scarpetta Beach, casual American cafe Tillie’s, Corso Coffee, The Beach Club and The Regent Cocktail Club. The coveted tables at the Restaurant at Baron’s Cove are even offering blue-plate specials on weekdays this fall.

Discounts on Cute South Fork B&Bs

Many South Fork hamlets were established in the 17th century. That means there are a plethora of historic houses that have been transformed into cute bed-and-breakfasts. Just a short walk to town, Amagansett’s 434 on Main is situated in a beautiful 1905 home with a perfect wraparound porch. On Shelter Island, the landmark inn, The Chequit, was recently overhauled by Salt Hotels, bringing a modern update to the old house. Its new restaurant Red Maple opened in August. The Hedges Inn in East Hampton offers plenty of charm (with modern-day renovations) right near the beach. All three are handing out steep discounts this fall.

Charming North Fork Inns

The South Fork dies down right after August ends. Up in the North Fork, however, high season is still going on through autumn. Cozy up next to the fireplace in the wood-filled dining room way out east at the Orient Inn. It offers five airy bedrooms with private baths. Built in 1863 by captain Jedediah Hawkins, the Jedediah Hawkins Inn has received a New York State Historic Preservation Award for its restoration. The stunning property hosts an acclaimed restaurant and speakeasy with cool secret passageways and trapdoors. For those who want to stick close to the vines, Shinn Estate Farmhouse features modern guest rooms in an 1880s farmhouse right in the center of Mattituck’s farms and vineyards.

The Hamptons Film Festival

Actors and filmmakers, including Alec Baldwin, Gwyneth Paltrow, Jerry Seinfeld and Steven Spielberg, have been known to spend ample time out East. So it should come as no surprise that the area is home to a critically acclaimed film festival. In its 23rd year, the Hamptons International Film Festival has screened numerous Best Picture Oscar winners. From Thursday, October 8 through Sunday, October 12, it’s showing independent and star-studded films across East Hampton, Southampton, Montauk and Sag Harbor such as Carol (with Cate Blanchett and Rooney Mara) by Todd Haynes and Spielberg’s Bridge of Spies with Tom Hanks.

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