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Since it first opened, North Fork Table & Inn has been widely regarded among the best — and most romantic — restaurants on Long Island. Credit: David Benthal

Few things spell love quite like watching the sun set over the Sound with a bottle of wine and that special someone by your side, which is why OkCupid’s first Chief Marketing Officer Melissa Hobley made the North Fork her home.

Lucky for you, she and Suzette Emma of Island Gatherings Picnic Co., which specializes in staging romantic occasions, shared their favorite date locations from Orient to Riverhead, day to night.

Whether you’re seeking extra sizzle to put a ring on it or a fun, lively setting to spark up a first date, hit these hot spots to put the fireworks back in your life. 


The dumplings, edamame and more from Opties and Dinghies in Orient (Photo Credit: Felicia LaLomia).

Opties and Dinghies 

1010 Village Ln, Orient, NY 11957

Hours: Open Fri-Wed, 8 a.m. – 8 p.m. Closed Thursdays

Impress a foodie with a trip to this mecca of dumplings, gelato and croissants located in the heart of Orient, with its charming seaside cottages and village square. “You really feel like you’re stepping into another era,” Hobley said. “And in the fall, it’s just beautiful.” Because nabbing a seat outside this tiny eatery is tricky, Hobley recommends getting your food to go and savoring it by the nearby marina.

Pastries made by Marie Eiffel. (Credit: Marie Eiffel, courtesy)

Marie Eiffel Market

184 N Ferry Rd

Shelter Island

Market Hours: Wed-Sun 7 – 6 p.m., Closed Tuesdays

Feel like you’ve traveled to another continent without venturing more than eight-minutes away at this charming French bistro on Shelter Island that serves Croque Monsieur, Croque Madame, and French toast all day long. Dive into lunch with melted a Brie and French ham sandwich, a grass-fed Hanger steak sandwich, or a Parisian sandwich. Don’t skip dessert, order a sweet treat to split such as their Bourbon infusion vanilla ice cream, a chocolate croissant, or a mini-Nutella donut. Sit by the waterfront deck to kick up date by a few notches.  

A couple enjoys the Harbes courtyard in 2019. (Credit: Elizabeth Wagner)

Harbes Family Farm 

715 Sound Ave, Mattituck, NY 11952

Hours: Open 7 days/week 10-6 p.m.

The scent of pumpkin is known to stimulate arousal, which is why Hobley recommends heading to this Mattituck farm, stocked with all manner of pumpkin-spiced drinks and baked delights. “They have live music on the weekends, you can have cider,” Hobley said. “It’s the ‘pick’ for a reason.” Get to know your date while strolling through their eight-acre U-Pick pumpkin patch, getting lost in their Wizard of Oz corn maze or hitching a ride on the Barnyard Adventure Hayride (available on weekends and holidays). The best way to make it to a second or third date is to take that pressure of your first, Hobley said.

Love Lane Kitchen’s outdoor patio (Credit: Monique Singh-Roy)

Love Lane Kitchen

240 Love Ln, Mattituck, NY 11952

Hours: 7 days/week Tues-Thurs 8-4 p.m., Fri-Sun 8-9 p.m.

This cozy Mattituck country eatery doesn’t have the word “love” in its name for nothing. Hobley said this spot is made for brunch dates (they serve until 2:00 p.m., every day of the week) without the high stakes of a whole night out. Share their generous breakfast tacos, lemon ricotta pancakes or Belgian waffles – with mimosas, of course.  

Enjoying a tasting at Eastern Front. (Credit: Cyndi Zaweski)

Eastern Front Brewing Co. 

13100 Main Rd, Mattituck, NY 11952

Hours: Mon 12 – 4 p.m., Tuesday 5 – 10 p.m., Wed and Thurs 5 – 8 p.m., Sat 12 – 9 p.m., Sun 12-4 p.m.

For a flirty, good time, Hobley recommends this small Mattituck craft brewery, offering an intimate, garden setting where you soak up live music during the day or under twinkling stars and string lights at night. If you want to impress a date with your pipes, check out their open-mic night, every Tuesday from 7-10 p.m. 

8 Hands Farm in Cutchogue. (Credit: Sara Austin)

8 Hands Farm

4735 Cox Ln, Cutchogue, NY 11935

Closed Mon and Tues, Thurs – Sat 9 – 5 p.m., Sun 9 – 3 p.m.

Watching adorable goats frolick and fuzzy chicks nuzzle with their mother hens has a way of leading to human cuddles and kisses, said Hobley, who loves this “farm-to-fork” destination for low-stakes, breakfast dates. She’s also a fan of their pastries, particularly their coconut chocolate almond scone, a rich treat that’s perfect to share over one of the best lattes you’ll find on the North Fork. “8 Hands is beloved by both the locals and the New York City folks because their food is just so amazing, and they do really good coffees as well,” said Hobley. Pick up meat to grill in their butcher shop if you’re ready to take your day date to night.


The beautiful views at The Halyard. (Credit: David Benthal)

The Halyard 

58775 County Rd 48, Greenport, NY 11944

M, T, W – closed, TH 4:30-9 p.m., Fri – Sun 12-3 p.m., 4:30-9 p.m.

The horizon beckons from every angle at this seaside perch situated at the Soundview Motel, which is why Hobley suggests booking a table at sunset for maximum impact. As if the ambiance isn’t seductive enough, Chef Stephan Bogardus, previously from Northfork Table & Inn, will tempt your tastebuds with swordfish to scallops, farm-fresh salads to vegetarian bowls. Start the date off right with a cocktail like the Moondog, a sweet-tart mix of Plymouth Gin, St. George Raspberry Brandy, Amar Abano and lemon, said Hobley.

The metallic bar at Black Llama shines. (Credit: Cyndi Zaweski)

Black Llama Bar 

300 Main Street, Greenport

Hours: Mon 5-10 p.m. T, W, TH 5-9 p.m. Fri 5-10 p.m., Sat 12-10 p.m., Sun 12-9 p.m.,

Raise your glass to love at this mixology dream spot, located next to hip-hotel, American Beech. Black Llama Bar is Hobley’s go-to for intimate occasions. Choose from a wide array of local wines, beers, bubbly, and signature drinks like their watermelon sangria/froze, a hybrid blend of strawberries, lemon, sugar, rosé, vodka served as a watermelon vodka floater, or their Stirling Smoke, a mix of mezcal, lemonade and matcha. Reserve a table ahead of time, as weekend nights tend to fill up. 


Greenport Harbor Brewing Co.

234 Carpenter St, Greenport, NY 11944

Hours: Sun-Thurs 12-7 p.m., Sat & Sun 12-8 p.m.

There’s no room for awkward silence at this lively Greenport brewery, which is always a scene on weekends, but has a new beer garden that’s made for laid-back, first dates that won’t have you shouting to be heard. Check out their website for a list of more upcoming events, including weekly trivia nights. 

The crew at Little Creek Oysters in 2017. (Credit: Randee Daddona)

Little Creek Oysters

Bootleg Alley, 37 Front St, Greenport, NY 11944

Hours: Closed Tues & Wed, Open Mon 12 – 7 p.m. and Thurs – Sun 12 – 9 p.m.

Take in the moon and harbor lights over a tray of fresh-shucked oysters at this intimate shack, overlooking the water in Greenport. Yes oysters have a reputation as an aphrodisiac, but so does a quiet table for two away from the hustle and bustle of Front Street, an ideal setting for getting to know someone better.


North Fork Table & Inn remains a top restaurant in Southold. (Credit: David Benthal)

Northfork Table & Inn

57225 Main Rd, Southold, NY 11971

Hours: Closed Mon & Tues, Wed & Thurs 5-10 p.m., Fri & Sat 5-10:30 p.m., Sun 5-10 p.m.

If you’re ready to pop the question, dazzle your date with a dinner prepared by Michelin-starred chef John Fraser at the Northfork Table & Inn. Before you nibble away the night by candlelight, lock eyes over their Stone Fruit Old Fashion, a seductive blend of preserved peaches, plums, cherries, Four Roses single, lovingly prepared by Hobley’s favorite mixologist. “Melody[MF2]  is one of the best bar tenders in the country, not just in New York,” Hobley said, adding that sitting side by side at the bar is a good way to ease those big-date jitters. “Melody will actually help you make the date less awkward.” 

A toast to Palmer Vineyards in Riverhead. (Credit: Krysten Massa)

Palmer Vineyards

5120 Sound Ave, Riverhead, NY 11901 

Hours: Mon- Thurs 11 – 6 p.m., Fri 11 – 7 p.m., Sat and Sun 11 – 6p.m.

A lush vineyard – sans bachelerotte party – but with chilled bubbly on hand is a sure way to get a “yes.” “All of the vineyard picnics at Palmer are beautiful because they allow us to set up [their picnic experiences] on the lawn or within the vines. It’s so private and beautiful,” Emma said. Sparkling not your thing? Try their 2020 Sauvignon Blanc if you like white wine, or the 2015 Old Roots Merlot, “a deep velvety red, which comes from their original planted vines and is hand harvested,” she said. Walk-ins welcome—as long as you’re not inviting all your friends. 

A romantic evening on the water. (Credit: Courtesy Layla Sailing)

Layla Sailing

1410 Manhanset Ave, Greenport, NY 11944

Nothing takes your breath away quite like sailing under a pink North Fork sky—and a diamond. If that’s what you have in mind, Emma suggests Layla Sailing, which offers two-hour sunset cruises ($700), which includes ice, water, blankets, a Bluetooth speaker, as well as cutlery, plates, cups, and other serving platters and utensils. Pack your own picnic basket, sweaters and of course your phone to capture the magic moment. “If you want to create romance, they’re going to bring it,” said Hobley. For more information or to book your charter, visit

The view from Kontokosta Winery. (Credit: Randee Daddona)

Kontokosta Winery

825 North Rd, Greenport, NY 11944

Hours: Sun-Fri 11 – 5 p.m., Sat 11 – 6 p.m.

Wander through the vines as the sun dips into the Sound at Kontokosta Winery, which Hobley calls a magical place to celebrate special anniversaries or big dates. Sample one of the North Fork’s best Sauvignon Blancs or Viogniers as you stroll along the bluffs for a date to remember.