10 East End Eateries Taking Fall Outdoor Dining to Next Level

Calissa stunning fall outdoor dining space, Photo: Courtesy
Calissa stunning fall outdoor dining space, Photo: Courtesy

As the temperature drops, our natural instinct is to retreat indoors where its warm, but to do so is to miss out on the East End’s fall outdoor dining experience, where the stunning beauty of the changing leaves and the sense of tranquility wafting through the air can be experienced first-hand. Several local restaurants are taking full advantage of this picturesque season with outdoor dining designs that go above and beyond the typical setup—and the best part is, they’re heated! Cozy igloos, toasty tents and serene garden spaces await you at these 10 East End eateries.

Calissa offers guests the chance to enjoy authentic Greek cuisine and an award-winning wine selection in its fantastical outdoor space, seating up to 100 diners, and in its stunning indoor space. Just in time for the fall and winter ahead, Calissa has installed a 40-foot tent with heating, a state-of-the-art sound system, Mediterranean lanterns and decorative fire pits. The restaurant also has a new Bazaar open Thursday, October 29 through Halloween, replete with a Caravana Pop-Up Shop direct from Tulum, a Farmers Market with Cascun Farms, Jimmy’s Food Truck serving gyros and salads, and a special Whispering Angel rosé menu. 1020 Montauk Highway, Water Mill. 631-500-9292, calissahamptons.com

Moby's heated outdoor dining space, Photo: Courtesy
Moby’s heated outdoor dining space, Photo: Courtesy

Moby’s Restaurant offers extensive heated garden seating with the sprawling Garden Tent that can seat up to 80 guests in a covered outdoor dining setup. And the new Moby’s Lodge has completely redesigned the existing patio space, elevating it to an ultrachic blend of cabin and beach styles, featuring mid-century modern furniture, textiles and elevated cozy touches throughout. Seating up to 40 guests in both dining table and lounge configurations, the patio space is heated and covered, with expansive windows on two sides (open weather permitting). With both an outdoor private dining room, the Sicilian Room, and larger party tables available in the Lodge, Moby’s is able to accommodate groups of up to 10 guests through Thanksgiving weekend. 341 Pantigo Road, East Hampton. 631-604-2227, mobysny.com

The igloos at Ram's Head Inn, Photo: Courtesy
The igloos at Ram’s Head Inn, Photo: Courtesy

The Ram’s Head Inn has bolstered their expansive outdoor dining area with the addition of five heated igloos, outfitted with baskets of blankets, heaters and twinkle lights. Guests can relax and enjoy beachside views of Coecles Harbor while enjoying the new Ram’s Head menus and drink list throughout the fall and winter. Igloos can be reserved for up to two hours for groups of at least four adults, maximum of eight guests, at no additional cost to the dining bill. Walk-in parties of up to eight people may enjoy any igloo not already reserved. Inn staff use an electrostatic sanitizing spray after each reservation to ensure the experience is safe for all. 108 Ram Island Drive, Shelter Island Heights. 631-749-0811, theramsheadinn.com

The roaring fire at Estia's Little Kitchen, Photo: Courtesy
The roaring fire at Estia’s Little Kitchen, Photo: Courtesy

Electronic heaters have become increasingly popular this year due to many East End restaurants staying open for outdoor dining into the fall, but while all that technology is much-appreciated, there’s something so classic and natural and about eating with the heat of a roaring fire. That’s exactly what you get at Estia’s Little Kitchen, with picnic tables spaced six feet apart, of course. Enjoy breakfast, lunch, dinner and margaritas in the garden or at the charming outdoor pickup station. Estia’s is open 10 a.m.–3 p.m. Wednesday–Monday, and dinner is served Friday and Saturday, 5–8 p.m. 1615 Sag Harbor Turnpike, Sag Harbor. 631-725-1045, estias.com

Waterside dining is harder to find as the weather gets colder, but A Lure Restaurant has the perfect solution. Get cozy under their enclosed, heated tent overlooking the water while enjoying the bounty of the sea and more. 62300 Main Road, Southold. 631-876-5300, alurenorthfork.com

Fall leaves sliding down Old Stove Pub's clear tent, Photo: Courtesy
Fall leaves sliding down Old Stove Pub’s clear tent, Photo: Courtesy

Closed for three years before reopening in July under new ownership, the Old Stove Pub returned to Sagaponack with an updated design including an expertly arranged patio and garden space that’s only gotten more exquisite as we’ve entered the fall. The space now places tables under a large, heated tent with autumn leaves gliding across the clear roof as up to 50 diners enjoy classic Greek dishes Wednesday–Sunday, with Pub Night specials on Wednesdays, and brunch from 11:30 a.m.–3:30 p.m. on Sundays. 3516 Montauk Highway, Sagaponack. 631-537-3300, oldstovepub.com

Gurney’s Montauk Resort & Seawater Spa is introducing seaside bungalows to bring guests a magical and socially distant experience this fall. 290 Old Montauk Highway, Montauk. 631-668-2345, gurneysresorts.com/montauk

Buoy One Riverhead's festively decorated tent, Photo: Courtesy
Buoy One Riverhead’s festively decorated tent, Photo: Courtesy

Buoy One already has some of the freshest, most flavorful seafood in Riverhead, so the addition of an open, heated tent is just a bonus. Their classic outdoor seating and takeout are still available, too, so the options are nearly as plentiful as the robust menu. 1175 West Main Street, Riverhead. 833-286-9663, buoyone.com/riverhead-1

You’d be forgiven for thinking Stone Creek Inn was hosting a culinary festival with its pointed tents, charming string lights and Bar Car, but this magical scene is the restaurant’s norm this fall. Open Wednesday–Sunday, Stone Creek Inn serves up clam chowder, grilled venison, Filet Mignon Au Poivre and more. 405 Montauk Highway, East Quogue. 631-653-6770, stonecreekinn.com

The cabanas at Southampton Social Club, Photo: Courtesy
The cabanas at Southampton Social Club, Photo: Courtesy

While the very nature of Southampton Social Club is to be social—meet new people, talk, dance—2020 has created an increased demand for privacy and distance, which owner Ian Duke was quick to adapt to. The South Beach–inspired, curtained cabanas allow up to 12 guests, including frequent A-listers, to talk and eat in their own space without the prying eyes of other diners. The plush pillows and cushions provide ample comfort, and the pleasures of bottle service add a further bit of comfort. The exclusive cabanas are no doubt enticing, but the rest of the outdoor dining area is just as splendid, with safely-spaced, umbrella-covered picnic tables available to lunch and dinner guests. 256 Elm Street, Southampton. 631-287-1400, southamptonsocialclub.com

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