Part of this season’s Shelter Island renaissance, the Chequit hotel has three restaurants from North Fork chef Noah Schwartz, and this New American is farm-to-table focused. Schwartz’s signature smash burger is on the menu, along with steaks, homemade pastas, a pulled-duck barbecue, and a raw bar. In addition to the dining room with a large center bar and an antique billiard table, there is a wrap-around porch.

There are only a few places where you can actually dine on the sand out east, and this scenic Montauk spot with spectacular sunsets is one of them. Tuna crudo with papaya, pickled serrano, and toasted sesame is a great local starter, and soy-glazed halibut with sushi rice and red curry coconut; or dry-aged ribeye with crispy smashed potatoes are solid entree choices.

This funky Montauk bar made history when the Rolling Stones regularly played pool and drank there in the ‘70s, and while it still attracts a big nightlife crowd, the outdoor space has morphed into a lovely dining area where you can opt for a range of classics, from fish ’n’chips to seafood paella or a NY strip steak.

Located within picturesque Amagansett Square, the restaurant owned and operated by Wolffer Vineyard attracts an interesting crowd and serves an array of wine by the glass - largely from its Wolffer, not surprisingly. The approachable menu includes an extremely crisp chopped Greek salad; and seared tuna with black forbidden rice.

Open nearly 35 years and a bit intimidating as it was a high-end haunt for such discerning diners as Paul McCartney, Brad Pitt, Richard Gere, Gwyneth Paltrow, Martha Stewart and Alec Baldwin, this Tuscan-influenced seasonal spot in East Hampton suddenly looks like a relative bargain next to some of the area’s loftily priced menus.  The legendary free-range chicken, served with crave-worthy garlic and parmesan Yukon potatoes is still just $33, and there is a sparkling rose by the glass for $15.  Save room for the massive tartufo. 

There are few outdoor areas prettier than the garden at this second location of Dopo. Like the original in Sag Harbor, chef Maurizio Marfoglia’s pastas — such as paccheri with slow-cooked pork ribs or authentic creations including braised octopus with manila clams and ′nduja sausage — taste as they would in Italy. Regulars here know to order wafer-thin flatbread drizzled with olive oil and sprinkled with rosemary and sea salt to start a meal.

Closed for over a year, the dining room within the captivating Maidstone hotel across from East Hampton’s pond has reopened with chef Andrew Doran at the helm, and it’s still a bit under the radar. Sushi is now on the menu. In addition to sashimi made with fresh local catch and classic maki, there is a vegan roll with shiitake, cucumber, carrots, and plantain. Among the entree offerings are linguini with clams laced with Chardonnay; and Asian-roasted Scottish salmon. The Living Room has always been pet friendly, and this year there is a partnership with the Farmer’s Dog, so treats abound.

The popular Upper East Side steakhouse may have temporarily shuttered this year, (a new incarnation is due to open on 60th Street this fall), but the Southampton outpost has been going strong.  Chopped salad that can be topped with shrimp, chicken or salmon,  is a longtime favorite, as are crispy sushi, Long Island duck, and a range of steaks.