Long Island

Wine, Bites, and Vineyard Views

September 11, 2026 | What To Do

By: Ashley Rea

Summer may be winding down, but some of the best days on Long Island are just beginning. As the first signs of fall arrive, warm afternoons, cooler evenings and harvest season create the perfect excuse to spend a day among the vines.

And while the wine may get you through the door, these North Fork vineyards offer plenty to snack on while you stay awhile. From cheese and charcuterie to authentic Mexican dishes and wood-fired pizza, these four wineries pair their pours with bites that make them destinations in their own right.

Paumanok Vineyards

Credit: Paumanok Vineyards

A glass of wine and a cheese board overlooking the vines is a classic North Fork combination, and Paumanok Vineyards makes it easy to settle in for the afternoon. The family-owned winery has been producing estate-grown wines in Aquebogue since 1983, with a portfolio that ranges from crisp whites and dry rosés to Cabernet Franc, Merlot and other structured reds.

Alongside its wines, Paumanok offers a seasonal menu designed with pairing in mind. Cheese and charcuterie, small plates and sandwiches give visitors plenty to enjoy between sips, with current offerings ranging from a Lebanese platter with hummus, olive tapenade and roasted peppers to a prosciutto, ricotta, apple and fig jam combination.

Best of all for those not quite ready to say goodbye to summer, outdoor seating is offered through November, weather permitting. Grab a table outside, order a tasting and let an afternoon among the vines ease you into the new season.

RGNY

Credit: RGNY

For something beyond the traditional wine-and-cheese experience, head to RGNY in Riverhead. The Mexican-owned winery brings its heritage into the tasting room, pairing North Fork wine country with flavors you might not expect to find during a vineyard visit.

RGNY currently offers a full menu of authentic Mexican food alongside the cheese boards and artisanal snacks associated with a winery afternoon. Visitors can also explore wine experiences ranging from traditional tastings to blending sessions, making it an easy destination to build an afternoon around.

With harvest-season hours continuing through October and outdoor tables available, RGNY is especially well suited to those sunny early-fall days when you're not quite ready to head inside. Come for the wine, stay for the food and enjoy a North Fork afternoon with a distinctly different point of view.

Jamesport Vineyards

Credit: Jamesport Vineyards

At Jamesport Vineyards, the food deserves just as much attention as what's being poured. One of the North Fork's oldest vineyards, the family-run winery is also home to Little Oak Wood Fired Kitchen, where a roaring wood-fired oven turns seasonal ingredients into shareable plates and handcrafted pizzas.

The constantly changing menu takes inspiration from what's being harvested across the East End, with ingredients sourced both locally and, in some cases, directly from the vineyard's own garden. Everything from oven-warmed Sicilian olives to meatballs and Neapolitan-inspired pizzas is designed to complement Jamesport's estate-grown wines.

Choose a table on the covered patio or settle into an Adirondack chair overlooking the vineyard and gardens. With wine in your glass and something warm from the wood-fired oven on the table, Jamesport Vineyards practically captures early fall on the North Fork in one afternoon.

Rose Hill Vineyards

Credit: Rose Hill Vineyards

Tucked away in Mattituck, Rose Hill Vineyards offers the kind of relaxed setting that makes it easy to lose track of an afternoon. The sustainably farmed vineyard welcomes guests for tastings and light bites, with an outdoor patio overlooking the vines when the weather cooperates and a cozy library waiting inside when those cooler fall days arrive.

The food menu keeps things perfectly suited for grazing over a tasting. Charcuterie and Mediterranean boards are joined by options like whipped ricotta and crostini, warm pretzels, marinated olives and prosciutto, burrata and arugula sliders.

It's an especially fitting destination for this in-between season: spend a sunny afternoon outside with a crisp glass of wine, or embrace the first chilly day of fall with a red and a seat inside. Either way, Rose Hill offers plenty of reasons to slow down and stay awhile.

Sip Into the Season

You don't have to choose between holding onto summer and getting excited for fall. On the North Fork, September offers a little bit of both—sunny vineyard afternoons, the start of harvest season and just enough crispness in the air to make a glass of red and something warm to eat sound especially inviting.

Whether you're sharing a cheese board in Aquebogue, digging into Mexican fare in Riverhead, ordering a wood-fired pizza in Jamesport or settling in for light bites in Mattituck, these four wineries make a delicious excuse to head east and sip your way into fall.

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