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As the air cools down, the north fork of Long Island is hitting its peak. The 30-mile-long peninsula on the East End is the perfect setting for a fall escape or holidays savored with friends and family.

The North Fork is peppered with quaint towns, but Greenport, incorporated back in 1838, has the most to offer visitors, thanks to its walkable village filled with picture-perfect homes, shops, and restaurants. Greenport also offers some of the best accommodations on the north fork.

Stay in Town or Go for the View

The shabby-chic Morning Glory Bed and Breakfast in Greenport is an editorial-worthy inn recommended by Harper’s Bazaar and New York Magazine. Housed in a historic farmhouse just a short walk from Greenport’s restaurants and galleries, its three white-washed guest rooms feature private baths, fireplaces, and luxurious linens.

For an equally relaxed experience, make your way to the Shinn Estate Vineyards & Farmhouse Inn, where you can start your day with a frittata made with eggs from the inn’s own chickens.

The SoundView Greenport hotel offers water views, as well as a modern restaurant with indoor and outdoor seating and a clubby, nautical-inspired piano bar. After a day spent exploring vineyards and farm markets, you can kick back by a beachside bonfire, or hang out in the hotel’s comfortable common areas, surrounded by works by local artists.

Stay and Dine in One Location

The North Fork is home to some renowned restaurants, such as The North Fork Table & Inn in Southold, founded by the late chef Gerry Hayden, a three-time James Beard Award nominee. Hayden helped pioneered the local farm-to-table movement, and established an ambitious program focused on organic and biodynamic produce and local pork and duck. The restaurant is now run by his pastry-chef wife, Claudia Fleming, and Hayden’s protege, a fellow North Fork local and Culinary Institute alumnus, Stephan Bogardus.

For those who want to stay close to their meal, the establishment also runs a four-room inn in a renovated farmhouse on the property. Rooms are minimalist with luxury bedding and bath amenities. The included breakfast may be reason enough to choose staying at The Inn.

At American Beech, a boutique hotel and restaurant co-owned by Argentinian fashion designer Alex Vinash, who also runs a boutique there, you can dine in a tropical, candle-lit setting. Vinash and partner Brent Pelton’s three-year-old complex has become a center of stylish Greenport life with special events often filling the courtyard and property. The restaurant blends Greenport’s farming, fishing and vineyard-filled history to deliver a modern American menu featuring dishes like braised short ribs, wild mushrooms and parsnip pasta, and branzino (European bass) with tomato broth, fennel, butternut squash, and purple potatoes.

After dinner, you can sip a cocktail or glass of the hotel’s private-label rosé beside an indoor-outdoor fireplace at the hotel’s lively bar. Wrap up your evening by heading to one of the property’s beach-chic rooms or apartments, where you will find all the comforts, including a stocked minibar and fridge, Frette beach towels and bikes.

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