Two Forks, One Weekend: The East End Itinerary
The east end of Long Island has always invited a choice: wine country or ocean beaches, quiet harbors or destination dining. We say skip the choice. With a thoughtful route and a few ferry crossings, a long weekend is enough to experience both sides without rushing a single tasting or sunset.
This Two Forks, One Weekend itinerary is the route Luxury Beach Getaway recommends most to guests staying across the Hamptons and North Fork. Friday starts in wine country with a farm-to-table dinner near Southold. Saturday’s ferry carries you from Greenport to Sag Harbor. Sunday closes with a Montauk lighthouse morning before the drive west. Every stop below is one we have visited or sent guests to ourselves.
Day 1, Friday Evening: Arrive on the North Fork
The North Fork is the right opening act for an East End weekend. The pace is slower, the wineries are open later than the tasting rooms on the South Fork, and the drive out from the city is about thirty minutes shorter than continuing on to East Hampton. Aim to leave the city by mid-afternoon so you can check in, breathe out, and be at your first tasting before the golden hour.
Bedell Cellars, Cutchogue
Bedell sits on Main Road in Cutchogue, a working vineyard with one of the most polished tasting experiences on the fork. The barn-style room opens onto a wide indoor-outdoor picnic lawn, and weekend afternoons typically include live music. Pair the chardonnay with a charcuterie board and you have an arrival ritual that takes the edge off the drive without rushing the rest of the night.
- Rating: 4.4 stars, 187 reviews
- Address: 36225 Main Rd, Cutchogue, NY 11935
- Hours: Friday and Saturday 11 AM to 7 PM, Sunday to Thursday 11 AM to 6 PM
- Phone: (631) 734-7537
- What to order: Estate chardonnay, taberna red blend, seasonal charcuterie
Macari Vineyards, Mattituck
If you have time for a second tasting before dinner, drive a few miles west to Macari. The estate stretches across roughly 500 acres along the Peconic Bay side of the fork, and the bayside breeze makes the picnic tables some of the most pleasant outdoor seating in the region. Macari is particularly worth the stop for guests who lean toward whites and rosés, and their sauvignon blanc is consistently among the best on Long Island.
- Rating: 4.5 stars, 466 reviews
- Address: 150 Bergen Ave, Mattituck, NY 11952
- Category: Winery
- What to order: Sauvignon blanc, Lifeforce chardonnay, Rosé
Dinner at North Fork Table & Inn, Southold
Reserve your Friday dinner well in advance and reserve it here. North Fork Table & Inn has set the bar for destination dining on the fork for nearly two decades, and the seasonal American menu reads like a love letter to the farms and oyster beds within a fifteen-mile radius. The dining room is warm and low lit, the wine list leans local, and after dinner you can walk the gardens before turning in.
- Rating: 4.5 stars, 399 reviews
- Address: 57225 Main Rd, Southold, NY 11971
- Phone: (631) 765-0177
- What to order: Local oysters to start, the seasonal tasting menu, a North Fork chardonnay pairing
A recent guest, Nitzan, called it “the perfect North Fork getaway, the food was exceptional, the hospitality even better.”
Day 2, Saturday Morning: A Slow North Fork Start, Then the Ferry South
The genius of the Two Forks weekend is the Saturday morning crossing. Instead of driving back west on the Long Island Expressway and looping south through Riverhead, you drive seven minutes onto the North Ferry from Greenport, cross Shelter Island, take a second ferry into North Haven, and step out onto the South Fork in time for lunch in Sag Harbor. The boats save you well over an hour and turn dead transit into one of the prettiest stretches of the weekend.
Love Lane Kitchen, Mattituck
Save Friday’s farm-to-table dinner for an unhurried morning here. Love Lane Kitchen anchors Mattituck’s tiny commercial strip and runs on locally sourced eggs, North Fork bacon, and from-scratch biscuits and pastries. It is the kind of place where the regulars know the staff, and a coffee and a seat by the window is the right way to ease into the day.
- Rating: 4.5 stars, 1,327 reviews
- Address: 240 Love Ln, Mattituck, NY 11952
- Category: American cafe
- What to order: The breakfast sandwich, the granola bowl, a flat white
Harbes Family Farm, Mattituck
A short detour from Love Lane lands you at Harbes, the most family-friendly farm stand on the fork and a working farm that takes its produce seriously. Pick up jam, sweet corn, and the seasonal cider donuts to take with you, and let the kids burn a half hour in the barnyard before you point the car toward Greenport.
- Rating: 4.3 stars, 704 reviews
- Address: 247 Sound Ave, Mattituck, NY 11952
- What to grab: Sweet corn, apple cider donuts, peach jam, a six-pack of farm eggs
Lavender By the Bay, East Marion
If you are visiting between mid-June and late July, pull off Main Road in East Marion for the bloom. Twelve acres of lavender stretch toward the bay, and even on a busy summer Saturday it is one of those rare places that quiets every conversation down for a few minutes. Outside peak bloom, the farm shop is still worth a stop for the essential oils, sachets, and lavender honey.
- Rating: 4.4 stars, 666 reviews
- Address: 7540 Main Rd, East Marion, NY 11939
- Best time: Late June through late July for peak bloom
- What to grab: Lavender essential oil, sachets, lavender honey
Greenport Harbor and the Ferry South
Spend an hour walking Greenport itself. Front Street and Main Street are dense with boutiques, antique shops, and one of the prettiest little carousels in the state. If you have time, stop in at Greenport Harbor Brewing Company for a flight before the ferry. The brewery’s pour list is local in a way that the wineries cannot match, and the front patio looks straight at the harbor.
- Greenport Harbor Brewing Company: 4.6 stars, 157 reviews, 234 Carpenter St, Greenport, NY 11944
- Hours: Typically open daily, check the website for live music nights
From the ferry dock at the end of Wiggins Street, the North Ferry leaves every fifteen minutes for the seven-minute hop to Shelter Island. Drive straight across the island, with an optional fifteen-minute stop at Mashomack Preserve to stretch your legs in 2,039 acres of woodland, tidal creeks, and salt marsh, then queue for the South Ferry into North Haven.
Mashomack Preserve, Shelter Island
If you can spare ninety minutes between the two ferries, the visitor center loop trail at Mashomack is the right midday reset. Trails are well marked, you will see osprey nests and freshwater ponds, and the entrance fee is a small donation. Bring water and bug spray in summer.
- Rating: 4.8 stars, 307 reviews
- Address: 79 S Ferry Rd, Shelter Island, NY 11964
- Hours: Daily, dawn to dusk
- What to do: Visitor center loop, the green trail (1.5 miles), bird-watching
Day 2, Saturday Afternoon and Evening: Sag Harbor, the Beach, and a Bridgehampton Dinner
You will step off the South Ferry in North Haven with a fifteen-minute drive into Sag Harbor ahead of you, which is also the most efficient introduction to the Hamptons you can ask for. Park near Main Street, eat by the marina, and let the afternoon unfold.
Sag Harbor Whaling and Historical Museum
The whaling museum sits in a Greek Revival mansion at the head of Main Street, and a thirty-minute tour is a smart investment in context for everything else you will see this weekend. The collection spans scrimshaw, ship’s logs, harpoons, and a recreated nineteenth-century cooper shop, and the docents are sharp.
- Rating: 4.5 stars, 145 reviews
- Address: 200 Main St, Sag Harbor, NY 11963
- Hours: Seasonal, typically open daily late May through Columbus Day
- What to see: The Wickham collection, the captain’s quarters recreation
Coopers Beach, Southampton
If a real Atlantic beach afternoon is on the agenda, point the car west to Coopers Beach. It is the broadest, sandiest ocean beach on the South Fork, and the parking lot accepts day passes for non-residents. Lifeguards, bathrooms, a snack bar, and a long flat stretch of soft sand make it the easiest place to spend three hours doing absolutely nothing.
- Rating: 4.7 stars, 1,634 reviews
- Address: 268 Meadow Ln, Southampton, NY 11968
- Best time: Arrive before noon on summer weekends for parking
- What to bring: A canopy or umbrella, the snack bar exists but lines build
Dinner at Almond, Bridgehampton
Almond has been the South Fork’s quiet champion of farmstand cooking for two decades. The dining room is unassuming, the menu names its farms, and the wine list runs deep enough for serious drinkers without becoming intimidating. Reserve early in season, especially for a Saturday night, and ask about the kitchen’s daily fish.
- Rating: 4.4 stars, 312 reviews
- Address: 1 Ocean Rd, Bridgehampton, NY 11932
- Phone: (631) 537-5665
- Hours: Friday and Saturday 5 to 11 PM, Sunday to Wednesday 5 to 9 PM, Thursday 5 to 9:30 PM
- What to order: The mussels, the daily fish prepared “naked,” the hanger steak frites
Day 3, Sunday Morning: Montauk to the End and Back
Leave the South Fork lodging early. Montauk is at its best before the day-trippers arrive, and the drive from East Hampton to the lighthouse is one of the prettiest forty-five minutes on Long Island, with Napeague stretching wide on either side of the road.
Montauk Point Lighthouse
The Montauk Point Lighthouse has stood at the eastern tip of Long Island since 1796, commissioned by George Washington and still maintained as a working aid to navigation. Climb the 137 iron steps for a 360-degree view that on a clear morning reaches all the way to Block Island, then walk the bluff trail back along the surf line. The museum at the base is worth twenty minutes for the keepers’ quarters reconstruction alone.
- Rating: 4.8 stars, 309 reviews
- Address: 2000 Montauk Hwy, Montauk, NY 11954
- Hours: Seasonal, typically 10:30 AM to 4:30 PM weekends
- What to do: Climb the tower, walk the bluff trail, museum visit
Main Beach, East Hampton
On the way back west, ten minutes off Montauk Highway, Main Beach is the classic East Hampton beach for a reason. Soft sand, real surf, and a pavilion with showers and a snack bar that punches above its weight. If you only have an hour, go anyway.
- Rating: 4.6 stars, 46 reviews
- Address: 102 Ocean Ave, East Hampton, NY 11937
- Best for: A quick swim and a board walk before lunch
Parrish Art Museum, Water Mill
The Parrish is the South Fork’s serious art museum, and the Herzog & de Meuron building is itself worth the visit. The collection focuses on the artists who have worked on the East End from the late nineteenth century forward, including Pollock, de Kooning, Krasner, Porter, and Rivers. Plan ninety minutes minimum.
- Rating: 4.5 stars, 621 reviews
- Address: 279 Montauk Hwy, Water Mill, NY 11976
- Hours: Wednesday to Monday 10 AM to 5 PM
- What to see: The permanent East End collection, the current rotating exhibition
Wolffer Estate Vineyard, Sagaponack
End the weekend where the two forks really do meet in spirit. Wolffer is the most famous winery on the South Fork, the rosé is the signature, and the late-Sunday-afternoon tasting on the lawn is the right way to slow down before the drive home. The barn building and the sloped vineyards are some of the most photographed in the region for good reason.
- Rating: 4.4 stars, 717 reviews
- Address: 139 Sagg Rd, Sagaponack, NY 11962
- What to order: Summer in a Bottle rosé, the estate red, a cheese board
A Greenport Hold: Claudio’s
If the calendar bends and you want a final North Fork lunch, drive into Greenport for a dockside table at Claudio’s. The space has been a Greenport institution since 1870, the lobster roll is a baseline you should have on the trip somewhere, and the deck looks straight onto the harbor where you took the ferry yesterday.
- Rating: 4.4 stars, 1,667 reviews
- Address: 111 Main St, Greenport, NY 11944
- Phone: (631) 477-0627
- What to order: The lobster roll, raw oysters, a glass of local rosé
The Right Way to See the East End
The Two Forks weekend works because the East End is, despite the marketing, one place. Same farmstands. Same oyster beds. Same Atlantic. The forks just point in different directions. With one weekend, the right route, and a rental on each side, you get the full picture: the wine country mornings, the harbor afternoons, the ocean swims, and the long quiet drive past the lavender at the end.
When you are ready to plan the stay, browse our East End vacation rentals or reach out directly and our team will match you with the right home on each fork for the weekend you have in mind.
Frequently Asked Questions
Is it really possible to see both the Hamptons and North Fork in one weekend?
Yes, comfortably, as long as you use the Shelter Island ferries instead of driving back through Riverhead. The North Ferry from Greenport plus the South Ferry into North Haven is about twenty-five minutes door-to-door and saves at least ninety minutes of driving.
Which fork should we sleep on first?
Sleep on the North Fork Friday night and the South Fork Saturday night. The North Fork dinner reservations are easier to land on a Friday, and waking up on the South Fork on Sunday puts Montauk inside an easy morning drive.
What is the best season for a Two Forks weekend?
Late May through early October. June and September are the sweet spots: peak winery hours, beach weather, and noticeably fewer crowds than July and August. Lavender By the Bay peaks late June through late July.
How long are the ferry rides between Greenport and the South Fork?
The Greenport to Shelter Island North Ferry runs about seven minutes. The Shelter Island to North Haven South Ferry runs about five to seven minutes. Total transit, including the short drive across Shelter Island, is roughly twenty-five to thirty minutes.
Do we need a beach permit for Coopers Beach or Main Beach?
Both beaches require a daily parking fee for non-residents. Coopers Beach in Southampton sells day passes at the gate. Main Beach in East Hampton requires either a day pass or a non-resident parking pass that you can buy at East Hampton Town Hall during the week.
What if we want to add a fourth day?
Add it on the North Fork. A second North Fork day rewards a slow morning at Orient Beach State Park, a long lunch at one of our recommended waterfront spots, and a final tasting at Sparkling Pointe or Croteaux Vineyards. Our Longer Stays collection is built for exactly this kind of trip extension.
