Curated Collection · 25 stops
25 stops sorted by what the food actually is — 6 proper kitchens, 11 pizza windows and grill nights, and 8 rooms whose small plates are worth ordering. A cheese board on its own does not qualify.
Nearly every tasting room on the East End sells a charcuterie board, which is why searching for wineries with food returns almost the whole trail and helps nobody. So the 25 stops here are sorted by what you can actually eat: a kitchen with a menu, a truck or window serving something hot, or in-house plates that go beyond cheese. Four of them are not wineries at all — a cider hall, a farm brewery, a distillery, and a doughnut orchard — and they are here because they solve the problem better than most vineyards do. The other half of this question is what you may bring: outside food is banned at most of these houses, and outside alcohol is banned at every venue on Long Island, so the picnic stops are a separate and shrinking group named in the FAQ below. If you want the food to be the whole afternoon rather than an add-on, start with the six kitchens, then pair a neighboring winery for the tasting itself.
Lunch or dinner, most days open
Six rooms run an actual kitchen or café, so the food is a menu rather than a board — pizza, sandwiches, panini, plates. These are the ones to build a day around if nobody wants to drive somewhere else to eat.
Jamesport
Little Oak Wood Fired Kitchen shares the barn with the tasting room — wood-fired pizza and small plates, ordered as a meal rather than a snack.
The kitchen closes Tuesday and Wednesday, tastings are reservation-only and seated two to eight, and the room is 21+ after 6 p.m. Friday and all weekend. No outside food.
Peconic
Pizza, sliders, and snacks off an on-site menu, eaten in the Italianate hall or out on the veranda.
Open seven days from noon and 21+ on the official visit page. Walk in with a small party; eight or more need a reservation and a package. Weddings close the room, so check the calendar.
Southold
A full café inside the barn that opened at the end of 2024: Italian coffee, bakery, cheese and charcuterie, and an unusually deep tinned-fish list, with a full bar beside it.
Usually Wednesday through Monday, roughly 11:30 to 6, closed Tuesday. Four wines $25. Call first — the property was listed for sale in early 2026, with the tasting room reported to be staying open.
Riverhead
A rotating menu leaning Mexican — plates and cheese boards meant for the table — in the big Sound Avenue barn that used to be Martha Clara.
Walk in with ten or fewer if seats exist; 11 or more pre-book. The RG Tasting with pairings runs about $60. No outside food and no picnic area. Closed Tuesday and Wednesday in January and February.
Jamesport
Italian light fare done properly — antipasto, panini, ricotta bowls, spritzes — in the Jamesport room that used to be Diliberto.
Reservations highly recommended, tables of one to five, flights $32 to $35. Closed Monday and Tuesday. Six or more carries an automatic 20% gratuity.
Baiting Hollow · Cidery
Not a winery but the best-fed room on this list: a cider hall with a farm-to-fork café — pizza, sandwiches, nachos, pretzels, cider doughnuts — under fireplaces and oversized games.
Walk-up flights and pints, first-come seating, closed Tuesday and shut for two to three weeks in January. The Prohibition Room books on Resy for up to ten. No outside food, no dogs, and no high chairs.
Hot food, but tied to the day of the week
Hot food that comes and goes with the calendar. Some of these are dependable weekly fixtures, others only appear on event nights, so this is the group where checking the schedule before you drive matters most.
Riverhead
A wood-fired pizza truck parked at the 1983 Sound Avenue estate, alongside cheese pairings and the Albariño that was planted in New York first.
Truck runs Friday through Sunday in season. Walk in under six, reserve above it, and the mystery flight of four is $25. No outside food, coolers, or drinks. Hours change month to month.
Calverton
A pizza truck as a permanent fixture rather than a guest, next to lawn games, a gazebo, and west-facing sunset views.
Book a two-hour window between 12 and 5; walk in if there is space. Live music Saturday and Sunday 1 to 5 year-round, which makes it loud. No outside food or drinks.
Riverhead · Brewery
Food trucks every day the brewery is open, on a 40-acre farm with a hop yard and a beer garden — the answer when someone in the car does not drink wine.
Walk-up pints, first-come seating, closed Tuesday and Wednesday. Hop Rooms take 10 to 25 people in two-hour blocks from May to August. Buses and limos need a booking and must arrive before 2 p.m. No outside food.
Cutchogue
Burger Nights off the estate’s own Charolais herd — the rare case where the winery raised the beef as well as the Pinot Noir.
Seasonal, Thursday and Friday 4 to 8, and they book up. Closed January and February. Cheese and charcuterie the rest of the week, no outside food, and no limos or tour buses at any time.
Southold
Bedell’s little sister pours wines on tap and brings trucks in for its two evening series — Twilight Thursdays and Moonlight Mondays, the latter with pizza.
Walk in with 15 or fewer, larger parties by email, flights about $22. Hours rotate and event nights run later, so check the week you are going. Assume no outside food.
Peconic
A Grace & Grit smashburger pop-up takes over Thursday evenings in summer, next to the in-house snack and cheese menu at this women-led cellar door.
Pop-up runs 5 to 8. Walk in with five or fewer; groups of six to ten book 48 hours ahead at $20 a head. Closed Tuesday and Wednesday, and the hours conflict across pages — email to confirm.
Cutchogue
Cheese and charcuterie as standard, with food trucks on event nights and Wednesday music from 4 to 8 on the patio over the vines.
Walk in with 15 or fewer, flights $28 to $32. Sunday to Thursday 11 to 6, Friday and Saturday to 7 — but private events close it often, and the trucks only follow the event calendar. No outside food.
Bridgehampton
Food trucks on Friday and Saturday evenings in the Bridgehampton sculpture garden, with Mecox cheese, crackers, and salumi sold the rest of the time.
Daily 11 to 6, and those Friday and Saturday evenings often run to dark with music. Walk-ins fine, six or more reserve, five wines about $28, and Saturday adds $5 a person. No outside food.
Baiting Hollow · Distillery
A distillery rather than a winery: cocktails from a patio hut, snacks on site, and food trucks most weekends under a twin-cupola barn.
Walk-in, with live music Friday to Sunday. The Hidden Vault upstairs takes 11 to 20 people for $250 over two hours and is the one room here that lets you bring food or order delivery — stairs only. Confirm hours seasonally.
Aquebogue · Cidery
Cider doughnuts fried to order, plus pies, cookies, and apple bread — the only doughnut window on the trail, and reason enough for a stop with children.
No reservation. Flights are $10 for four ciders or $14 for all six on tap. Closes around 5:30, often shut Wednesday, and winter is weekends only. Peak doughnut lines run 20 to 30 minutes. U-pick is a separate address at 116 Manor Lane in Jamesport.
Mattituck
Cheese plates in the Wine Barn, and a whole working farm around it — farmstand, concessions, cider doughnuts, and ice cream on the same campus.
No reservations, first-come: three tastes $20 or five for $30. Seasonal, roughly April to early November, and the shared driveway with the farmstand makes autumn crowded. No outside food and no buses.
More than a cheese board, less than a kitchen
Almost every tasting room sells cheese and charcuterie, so that alone earns nothing here. These eight go further — sliders, sandwiches, mezze, caviar, a chef’s lunch — enough to hold an afternoon together without a proper meal.
Aquebogue
Seasonal small plates and sandwiches alongside the cheese and charcuterie — the closest thing to lunch among the benchmark estates.
Daily 11 to 5, Friday through Sunday to 6. Walk in with seven or fewer; eight or more email ahead, and weekends are best booked on Tock. No outside food or drink at all.
Cutchogue
Cheese, charcuterie, small plates and mezze at a 90-minute table on Oregon Road, built to be eaten slowly with the Pinot Blanc.
Reservations highly recommended on Tock, flights $26 to $36, groups capped at eight. Daily 12 to 6, Friday to 7. The library room is 21+. No outside food or drink.
Mattituck
A pizza pairing with some experiences, cheese and charcuterie with others, and a chef-cooked lunch if you book the private suite.
Reservations required, up to six a table: $40 for five wines or $75 in the barrel cellar. There is no food truck here — Southold Town bans them — and no outside food. Five-day cancellation.
Southold
Light fare made for a rosé afternoon: baguette and cheese, lobster-roll sliders, and dessert, in a pebbled garden among barns dating to 1749.
No reservations, first-come tables of eight that they will not split, daily 12 to 6 in season. The garden runs April to late November. No outside food, no party décor, and no vans, buses, or limos.
Mattituck
Charcuterie, a Mediterranean board, sliders, and pretzels at the quiet Oregon Road barn that holds a Governor’s Cup for its Cabernet Sauvignon.
First-come daily 11 to 6, flights $20 to $34, eight to a group, with an indoor library if the weather turns. No outside food, no buses, no bachelorette parties.
Cutchogue
A seasonal in-house menu at a boutique Cutchogue estate with a B&B upstairs and comparative tastings as the house format.
Walk in with six or fewer, $30 for four wines; groups of 7 to 15 prepay $35 a head. Confirm the hours, since the site and the booking system disagree. Wine-club members may bring small snacks; nobody else may.
Southold
Cheese, charcuterie, and caviar pairings — the only caviar service on the trail, which is what the sparkling-only list asks for.
Sit-down tasting house with reservations on Resy, general tables to six including drivers. Flights have run $20 for the flagship and $30 for the Prestige. No restaurant, no outside food, no picnics, and no pets.
Sagaponack
Cheese, charcuterie, and small plates at both Hamptons addresses — the seated Tasting Room on Sagg Road and the walk-up Wine Stand on Montauk Highway.
Tasting Room is seated on Tock and capped around eight to ten, and it closes for weddings; the Wine Stand is walk-in daily 11 to 8. No outside food at either, and no dogs.
Six run a kitchen or café you can order a meal from: Jamesport Vineyards has Little Oak Wood Fired Kitchen in the same barn, Raphael serves pizza and sliders, One Woman has an Italian café with a bakery counter and tinned fish, RGNY runs a rotating Mexican-leaning menu, Terra Vite does antipasto and panini, and Riverhead Ciderhouse — a cidery rather than a winery — has the fullest café on the East End.
Jamesport Vineyards is the one with pizza indoors from its own wood-fired kitchen, closed Tuesday and Wednesday. Raphael has pizza on the villa menu seven days a week. Palmer parks a wood-fired pizza truck Friday through Sunday in season, Baiting Hollow keeps a pizza truck as a fixture, and Corey Creek brings pizza in for Moonlight Mondays. Macari cannot have a truck at all — Southold Town bans them — so its pizza comes as a pairing instead.
At a shrinking handful, and almost none of them are on this page. Borghese encourages a picnic, Osprey’s Dominion allows one outright, Bridge Lane allows one if you clean up, Pugliese allows it at the outdoor benches, Pindar in designated areas outside, Jason’s in the picnic area, and both Duck Walks allow light snacks if you buy wine. Among the houses listed here there are only two exceptions: the Hidden Vault at Long Island Spirits lets a booked group bring food or order delivery, and Sannino allows wine-club members small snacks. Outside alcohol is banned everywhere on Long Island, without exception.
Jamesport Farm Brewery has a truck every day it is open. Palmer runs Friday to Sunday in season, Baiting Hollow keeps one on site, and Long Island Spirits has trucks most weekends. The rest are tied to a specific night: Corey Creek on Twilight Thursdays and Moonlight Mondays, Chronicle for a Thursday smashburger pop-up in summer, Channing on Friday and Saturday evenings, and Bedell only on event nights. Check the week before you drive.
McCall runs seasonal Burger Nights on Thursday and Friday from 4 to 8, cooked from the estate’s own Charolais beef — it is a cattle farm as well as a vineyard, and the nights book up. Chronicle hosts a Grace & Grit smashburger pop-up on Thursday evenings in summer, and Rose Hill and Raphael both keep sliders on the menu.
Woodside Orchards fries cider doughnuts to order and has a fire pit and a giant Connect Four, Harbes pours in a barn on a working farm with a farmstand, concessions, and ice cream on the same campus, and Riverhead Ciderhouse has a café, oversized games, and fireplaces — though no high chairs. All three are on the family-friendly list too.
For the seated houses, yes — Macari, Jamesport Vineyards, Terra Vite, and Mattebella all want a booking, and Lieb and Sparkling Pointe strongly recommend one. The kitchens and trucks are mostly walk-in: Riverhead Ciderhouse, Jamesport Farm Brewery, Woodside, Harbes, Rose Hill, and Croteaux all seat first-come. The exceptions worth calling about are McCall’s Burger Nights and any group of six or more.
21 of these 25 stops are wineries; the other 4 pour cider, beer, or spirits. If the group includes children, the family-friendly list overlaps this one heavily, and a crew arriving in one vehicle should start with the group outings list instead.