North Fork Dining & Wine Country: You Have Loads of Great Options

It’s six in the evening and the patio at Miss May’s is filling in. Somewhere behind the bar a shaker is going, a plate of shareable plates is landing on a table by the pool, and the only decision left is whether to eat here tonight or take a short walk back to your cottage first. Either way, dinner is close, easy, and already underway.

That’s the North Fork in one sitting: real cooking on Long Island’s East End, a working wine country a short drive in either direction, and farm stands selling fresh produce for tonight’s dinner. Here’s how to spend a weekend eating and drinking your way through it, starting right on property.

North Fork Resort at a Glance

• Miss May’s Kitchen & Bar on-site, with lunch and dinner service and live music on the patio Friday nights
• Minutes from Greenport village’s restaurant row and the North Fork’s wine country
• Farm stands and U-pick fields a short drive away for produce, cheese, and seasonal flowers
• A kitchen in every cottage, so a farm stand haul turns into your own meal just as easily as a night out
• Open April through November

Start Where You’re Staying

Miss May’s Kitchen & Bar sits right on property, which means a good seat for a North Fork sunset doesn’t require a reservation across town. The kitchen, led by Executive Chef Taylor May, a Culinary Institute of America graduate with time behind the bar at Silver Lyan in Washington, D.C., builds its menu around what’s actually in season on the North Fork: local seafood, North Fork produce, and shareable plates built for a table by the pool. The menu changes with the seasons, so check the Kitchen + Bar page for what’s currently on offer.

The cocktail list matches the setting: easy, unhurried drinks meant to be finished slowly on the patio rather than rushed between courses.

Fall hours: the kitchen is open Friday 4 to 9 p.m. and Saturday through Sunday noon to 9 p.m., and the bar stays open a bit later, Friday 2 to 10 p.m. and Saturday through Sunday 11 a.m. to 10 p.m. Miss May’s is closed Monday through Thursday. Live music runs on the patio every Friday from 7 to 10 p.m. through the end of October, weather permitting. Miss May’s is open through the end of October, weather permitting.

Greenport’s Restaurant Row, A Short Drive Away

Some nights call for a walk into the village, and Greenport delivers. It’s a small downtown with a genuinely deep bench of restaurants, several of them worth planning a dinner around.

The Frisky Oyster, at 27 Front Street, has been a North Fork dinner destination for years: a seasonal New American menu and the kind of room that fills up on a Friday night, so a reservation through Tock is worth making ahead.

American Beech, on Main Street, pairs a boutique hotel with a restaurant and bar that leans into contemporary American cooking and a lively patio scene, plus a late-night cocktail bar called Black Llama, open Friday through Sunday from 6 p.m. to midnight, for those still going after dinner.

1943 Pizza Bar, a few doors down on Main Street, started as a wood-fired pizza truck and grew into one of the more talked-about pizza spots on Long Island, using ingredients like house-made sausage and pork from 8 Hands Farm on its pies.

For sushi, Stirling Sake on Main Street is the village’s go-to for Japanese food, and it draws its own steady following.

The common thread: reservations move fast in July and August, especially on weekends, so it’s worth booking a table or two before you arrive rather than deciding on the fly. And when you’d rather keep the evening close to home, Miss May’s is right back at the resort for dinner, cocktails and an easy walk back to your cottage.

A Day in Wine Country

The North Fork’s wine country starts practically at the edge of Greenport and unfolds for twenty-some miles to the west, one of the more concentrated stretches of vineyards on the East Coast.

Kontokosta Winery, on North Road just outside Greenport, is the closest and easiest stop: the North Fork’s waterfront tasting room, set on a bluff over the Long Island Sound, open daily from 11 a.m. to 5 p.m. with no reservation required. It’s an easy first stop or a whole afternoon on its own, glass in hand, looking out over the water.

For a longer day trip west into Cutchogue and Mattituck, the list gets deep fast. Bedell Cellars and Macari Vineyards are two of the region’s best-known names. Lenz Winery, one of the North Fork’s oldest, focuses on Bordeaux-style wines. Bridge Lane keeps things casual with bocce courts and a family- and dog-friendly tasting room. Further afield, Croteaux Vineyards in Southold pours rosé exclusively, and Paumanok Vineyards in Aquebogue has been family-run since 1983. Most tasting rooms are open daily in season; weekends fill up, so an early start beats an afternoon arrival if you want a table.

A winery day pairs naturally with a cottage stay: come back and let the evening wind down at Miss May’s, or bring a bottle back and open it on your own patio instead.

Farm Stands Worth the Detour

The North Fork grows a lot of what shows up on North Fork tables, and several farm stands sit close enough to Greenport to fit into a morning without eating up the whole day.

Deep Roots Farm, a 7-minute drive away at 57685 Main Rd (NY-25) in Southold, is open daylight hours, seven days a week, with what’s available changing by season, making it an easy stop close to the resort. Sep’s Farm and Latham Farms, both toward Orient and East Marion, carry native produce and flowers in season. Sang Lee Farms in Peconic grows more than a hundred varieties of specialty vegetables, greens, and herbs, worth a stop for anyone who cooks. Catapano Dairy Farm rounds out the list for cheese. In midsummer, Bhavana Berries opens for seasonal U-pick blueberries, a good half hour for anyone traveling with kids.

Every cottage at North Fork Resort has its own kitchen, so a farm stand haul isn’t just a nice souvenir. It’s dinner. See the full guide to Long Island farms for hours and seasonal offerings before you go.

Making It Work Over a Weekend

A simple way to structure it: Friday night at Miss May’s, taking advantage of the live music on the patio after the drive out. Saturday for wine country, starting at Kontokosta and pushing west if the day allows, then a village dinner reservation made in advance for the evening. Sunday morning for a farm stand run and a slower breakfast back at the cottage before heading home, or staying one more night if the weekend got away from you, which it tends to.

Once you’re back at the resort for the evening, the car can stay parked. Miss May’s, your cottage and the resort are all right there, while Greenport is a short drive away and wine country and the farm stands build easily into the rest of the weekend.

Come Back for the Weekend, Then Come Back Again

A good meal has a way of turning one trip into a habit. Most guests find their way back to the same winery, the same table at Miss May’s, the same farm stand run, until the North Fork stops feeling like a destination and starts feeling like a place they just go.

For some, that eventually turns into a bigger question: what would it be like to have a place of our own here? When that happens, we’re happy to show you what ownership at North Fork Resort looks like.

Check availability and plan your next weekend of eating and drinking your way through the North Fork.

Frequently Asked Questions

What restaurant is at North Fork Resort?
Miss May’s Kitchen & Bar, on-site, serving lunch and dinner with a menu built around local seafood and North Fork produce that changes with the seasons. It’s open Friday through Sunday in the fall, with live music on the patio every Friday evening through the end of October, weather permitting.

What are the best restaurants near Greenport, NY?
Greenport’s village has a strong lineup, including The Frisky Oyster for seafood and New American cooking, American Beech for a lively hotel restaurant and bar, 1943 Pizza Bar for wood-fired pizza, and Stirling Sake for Japanese food. All are a short drive or walk from North Fork Resort.

What wineries are closest to North Fork Resort?
Kontokosta Winery, just outside Greenport on North Road, is the closest waterfront tasting room on the North Fork. For a longer wine country day, Bedell Cellars, Macari Vineyards, Lenz Winery, and Bridge Lane sit further west in Cutchogue and Mattituck, with Croteaux Vineyards in Southold and Paumanok Vineyards in Aquebogue as additional stops.

Are there farm stands near North Fork Resort?
Yes. Deep Roots Farm is a short drive away in Southold, and Sep’s Farm, Latham Farms, Sang Lee Farms, and Catapano Dairy Farm are all a short drive away as well. Every cottage has its own kitchen, so farm stand produce can go straight into dinner.

Do I need a car to eat and drink well during my stay?
Not for Miss May’s, which is on-site. Greenport village, wine country, and the farm stands are all a short drive from North Fork Resort.