North Fork

The Long Island Expressway ends and Route 25 begins, and somewhere in that transition — around Riverhead, where the highway dissolves into a two-lane road flanked by farm stands and hand-painted signs — the entire character of Long Island transforms. Strip malls and subdivisions give way to potato fields, grapevines strung along trellises, and century-old barns that have been repurposed into tasting rooms. The air changes too. It picks up salt from the Sound to the north, earth from the freshly turned fields, and something floral drifting off the vineyards that line both sides of the road. This is the North Fork, and it is the part of Long Island that most New Yorkers have either never visited or cannot stop talking about once they have.

I first drove the North Fork on a weekday in late September. The light was amber, the vines were heavy with fruit, and every farm stand along Route 25 was overflowing with corn, tomatoes, and peaches that smelled like they had ripened just for me. By the time I reached Greenport — the little harbor village at the end of the road — I had already pulled over four times. Once for wine, once for lavender, once for oysters, and once because a field of sunflowers demanded that I stop the car and stand there for a while. That is how the North Fork works. It is not a destination you rush through. It is a place that asks you, gently and repeatedly, to slow down.

Wine Country Without the Pretension

The North Fork is the birthplace of Long Island wine. The first vineyard — Hargrave, now Castello di Borghese — was planted in 1973, and in the five decades since, roughly 40 wineries have established themselves along the twin corridors of Route 25 and Route 48. The terroir here, shaped by the maritime climate and glacial soil, is often compared to Bordeaux, and the region produces exceptional Merlot, Cabernet Franc, Sauvignon Blanc, and an increasingly celebrated sparkling wine program.

What sets North Fork wine country apart from Napa or Sonoma is the scale and the attitude. These are not corporate estates with velvet ropes and $50 tasting flights. Most North Fork wineries are family-owned operations where the winemaker might pour your tasting, where dogs sleep on the patio, and where a bottle of excellent estate Merlot costs $28 instead of $80. The culture is agricultural, unpretentious, and genuinely welcoming.

Bedell Cellars in Cutchogue is the flagship. The estate produces some of Long Island’s most acclaimed wines — the Musée red blend and the Taste White are standouts — and the tasting room occupies a beautiful barn surrounded by vines. The art collection on display rotates seasonally and gives the space a gallery feel without trying too hard. This is where to start if you want to understand what North Fork wine can be at its best.

Sparkling Pointe in Southold focuses exclusively on méthode champenoise sparkling wines, and the results are remarkable. The Brut Seduction rivals sparkling wines at twice the price. Tastings happen on an elegant terrace overlooking the vines, and the whole experience feels like a celebration even on a random Tuesday afternoon.

Kontokosta Winery in Greenport combines serious winemaking with the most dramatic setting on the North Fork — a modern tasting room perched on a bluff above the Long Island Sound with panoramic water views. The wines are solid, the sunsets from the terrace are extraordinary, and on summer evenings with live music, it becomes the best bar on Long Island.

Macari Vineyards in Mattituck practices biodynamic farming on 500 acres, making it one of the largest and most ecologically committed estates on the East End. The Bergen Road Sauvignon Blanc is exceptional, and the farm-to-tasting-room ethos extends to the food program — cheese, charcuterie, and provisions sourced from their own fields.

A smart strategy: visit three to four wineries in a day, spacing tastings with food stops at farm stands. The scenery between wineries is half the pleasure — vineyards, farm fields, old churches, and views of the Peconic Bay flickering through the trees.

Greenport — The Village at the End of the Line

Greenport is the anchor of the North Fork — a compact, walkable harbor village that serves as both the region’s social hub and its most charming overnight base. The LIRR terminates here, the ferry to Shelter Island departs from the dock, and Front Street runs along the waterfront with a concentration of restaurants, shops, and maritime energy that feels distinctly New England despite being firmly on Long Island.

The village was a whaling port in the 19th century and a shipbuilding center into the 20th. That maritime heritage is visible in the architecture — clapboard storefronts, captain’s houses, church steeples — and in the working waterfront where fishing boats and oyster skiffs still tie up alongside pleasure craft. The carousel in Mitchell Park, a restored 1920s merry-go-round housed in a glass pavilion on the harbor, has become an icon of the village and spins on summer evenings against a backdrop of boats and sunset.

Front Street is where the action concentrates. Claudio’s, operating since 1870, claims to be the oldest family-owned restaurant in the United States and occupies a sprawling waterfront complex with dockside dining. The style is more festive than refined, but the clam bar and the harbor views are the point. For something more polished, Noah’s delivers inventive farm-to-table cooking in an intimate dining room — the duck breast with local cherry reduction and the Peconic Bay scallops are outstanding.

The Greenport Harbor Brewing Company taproom on Carpenter Street pours excellent craft beer in a former firehouse. The Harbor Ale is the flagship, but the seasonal releases — especially the harvest lager in autumn — are worth seeking out. On warm evenings, the outdoor seating fills with a mix of locals, weekenders, and day-trippers from the LIRR, all sharing the same easy pace.

Lavender By the Bay

In East Marion, roughly halfway between Southold and Orient Point, Lavender By the Bay sprawls across 17 acres with over 80,000 lavender plants — one of the largest lavender farms in the United States. The farm grows both English and French varieties, and during peak bloom from mid-June through mid-July, the fields turn an almost unreal shade of purple that stretches to the horizon.

Walking the rows at Lavender By the Bay is a sensory experience that transcends the visual. The fragrance is extraordinary — dense, sweet, and calming in a way that photographs cannot convey. Bees work the blooms. The Long Island Sound glimmers beyond the field edges. The whole place radiates a peace that feels curated by nature rather than design.

The farm shop sells lavender bundles, essential oils, sachets, honey, and dozens of lavender-infused products. The u-pick option during bloom season lets you cut your own bundles to take home. Arrive early on weekends — this has become one of the most popular and most photographed destinations on Long Island, and the parking lot fills by mid-morning during peak bloom.

Orient Point — Where the Fork Ends

Drive east past Greenport, past East Marion, past the lavender fields, and the North Fork narrows to a slender finger of land pointing at Connecticut across the Sound. Orient Point is the terminus — a windswept, hauntingly beautiful landscape of salt marshes, boulder-strewn beaches, and maritime forest that feels more like Maine than Long Island.

Orient Beach State Park occupies a spit of land extending into Gardiner’s Bay with a rare maritime red cedar forest, a long sandy beach, and views across to Shelter Island and the South Fork. The swimming is calm — this is bay water, not ocean surf — and the birding is excellent. Ospreys nest on the platforms along the approach road, and migrating shorebirds gather on the sandbars in spring and fall.

The Cross Sound Ferry departs from Orient Point for New London, Connecticut — a scenic 90-minute crossing that opens up interesting loop trip possibilities. You can drive the North Fork, ferry to Connecticut, and return via a different route, or vice versa.

Orient village itself is a tiny, pristine hamlet with white clapboard houses, a country store, and the kind of deep quiet that only comes from being at the very end of the road. The Oysterponds Historical Society maintains several preserved buildings worth a visit. This is not a place for nightlife or shopping. It is a place for walking, watching the water, and letting the pace of the land slow you down to its rhythm.

Farm Stands and the Agricultural Heart

The North Fork is farm country first and wine country second. Agriculture has defined this landscape for 350 years, and the farm stands that line Route 25 and the back roads are as much a part of the experience as any tasting room.

Briermere Farms in Riverhead is legendary for its pies — blackberry, raspberry, blueberry, peach — baked daily with fruit from their own fields. The line out the door on summer weekends is a fixture of North Fork life. Get there early. They sell out.

Wickham’s Fruit Farm in Cutchogue is a family operation dating to 1661, making it one of the oldest continuously working farms in America. Pick-your-own strawberries, peaches, and apples in season, plus a farm stand stocked with produce, jams, and cider.

Sang Lee Farms in Peconic grows Asian specialty vegetables alongside traditional crops using organic methods. Their farm stand carries produce you will not find anywhere else on the East End — baby bok choy, mizuna, daikon — alongside beautiful tomatoes and herbs. The Saturday morning farmers market in Greenport also sources from Sang Lee and other local growers.

The beauty of North Fork agriculture is its accessibility. You do not need an appointment or a reservation. You just pull over when the sign catches your eye, buy a bag of corn or a quart of strawberries, and eat them on the tailgate of your car in a vineyard parking lot. That is fine dining, North Fork style.

Peconic Bay Oysters

The waters surrounding the North Fork — Peconic Bay, the Long Island Sound, and the tidal creeks running between them — produce some of the finest oysters on the East Coast. The North Fork oyster industry has boomed over the past two decades, and the names are becoming known far beyond Long Island.

Widow’s Hole Oysters, farmed in Greenport Harbor, are briny, clean, and available at restaurants and raw bars throughout the village. Little Creek Oysters from Greenport and Peconic Gold from Southold are equally excellent. The cold, nutrient-rich waters and strong tidal flow produce oysters with a distinctive minerality and a salinity that balances beautifully with North Fork white wines.

Several restaurants offer oyster-focused menus. Little Creek Oyster Farm & Market in Greenport serves their own product raw, grilled, and Rockefeller in a casual waterfront setting. The combination of hyper-local oysters and a glass of Macari Sauvignon Blanc, sitting on a dock with the harbor in front of you, is about as good as eating gets.

Where to Stay

Boutique luxury: The Menhaden Hotel — Greenport’s newest boutique property sits on the harbor with a rooftop bar, modern rooms with waterfront views, and a design sensibility that nods to maritime heritage without kitsch. Walk to everything in the village. $280-450/night.

Waterfront retreat: Sound View Greenport — A mid-century motel transformed into a stylish retreat on the Long Island Sound. Private beach, excellent restaurant (The Halyard), and rooms with dramatic water views. $250-500/night in summer.

Classic charm: American Beech — A renovated motor lodge in Greenport with clean, contemporary rooms, a lively bar scene, and an on-site restaurant. The courtyard is a social hub on summer evenings. $200-350/night.

Budget-friendly: Greenport village rentals — Off-season and midweek, vacation rentals in and around Greenport offer the best value. Studios and one-bedrooms from $120-180/night. Check VRBO and Airbnb for options walking distance to the village.

Practical Details

The North Fork runs roughly east-west along two parallel roads: Route 25 (Main Road) and Route 48 (North Road, also called Middle Road in some sections). Wineries are scattered along both, with the heaviest concentration between Jamesport and Cutchogue. Greenport sits at the eastern end, about 20 miles from the first wineries near Riverhead.

The LIRR Ronkonkoma Branch terminates in Greenport — the ride from Penn Station takes about two hours with one transfer at Ronkonkoma. Service is more frequent on summer weekends. Driving from Manhattan takes roughly the same time on a good day, but eastbound Friday traffic and westbound Sunday traffic on the LIE can double that easily.

Cell service is reliable throughout. The climate is temperate maritime — summers are warm (75-85 degrees) with ocean breezes, springs and falls are mild and beautiful, and winters are quiet and cold (30-45 degrees). Most wineries and farm stands operate year-round on weekends but keep limited hours November through April.

Scott’s Pro Tips

There is a moment on the North Fork, usually in the late afternoon, when you are sitting on a vineyard patio with a glass of something local and the shadows start stretching across the rows. The vines glow in the low sun, a tractor rumbles somewhere in the distance, and the whole landscape settles into that golden stillness that only agricultural places know. It is not dramatic scenery — no mountains, no crashing surf, no skyline. It is something quieter and possibly more valuable: the beauty of land that has been tended for centuries by people who understand that the best things grow slowly. The North Fork does not compete with the Hamptons for glamour or with the Hudson Valley for grandeur. It simply offers what it has always offered — good soil, good water, good light, and the kind of pace that lets you actually taste what is in your glass.