Friends tasting wine on an outdoor patio at a Long Island winery

Curated Collection · 9 stops

Group Outings
on Long Island

9 stops that can actually absorb a crew — prepaid group flights, lawns where a picnic is allowed, bookable private rooms, and houses that take a bus if you call first. 8 on the North Fork, 1 on the South, with every cap, deadline, and picnic rule listed.

Built for a crew, not a couple

Most of Long Island wine country is quietly built against groups: tables cap at six or eight, vans get turned away at the driveway, and a reservation for ten simply does not exist. All 9 venues here do the opposite — a lawn or patio with room to spread out, a group package you can prepay, or a written policy that lets a hired vehicle pull in. Three of them are not wineries at all, and that is usually the point: a farm brewery, a cider hall, and a distillery mean the person who does not drink wine still has something to drink. Budget $18 to $35 a head for a tasting, or $250 for a private room, and assume six or more needs a phone call first. The seated estates that cap the table and refuse vans are the date-night list instead.

North Fork

West to east — Baiting Hollow through Southold — so neighboring lawns sit next to each other on the page.

Second-story deck overlooking the farm at Long Island Spirits

01 · North Fork · Baiting Hollow

Long Island Spirits

The East End’s first modern craft distillery, opened in 2007 inside a twin-cupola barn. Walk in for flights and cocktails, or book the upstairs Hidden Vault: 11 to 20 guests, $250 for two hours plus drinks.

The rare stop that holds a private group upstairs and a cornhole crowd on the patio at the same time.

The Hidden Vault is stairs-only, and the one room here that allows outside food or delivery. Food trucks most weekends, live music Friday through Sunday, 21+ to drink. Confirm seasonal hours.

2182 Sound Ave, Baiting Hollow, NY 11933
Vintage pickup at Riverhead Ciderhouse at sunset

02 · North Fork · Baiting Hollow

Riverhead Ciderhouse

A cider hall with a full café — pizza, sandwiches, nachos, pretzels, cider doughnuts — and a calendar of live music, trivia, bingo, line dancing, and dueling pianos. Walk up for flights and pints, or book the Prohibition Room, a private two-hour tasting for up to 10 on Resy.

A gathering hall rather than an orchard sip: patio, gazebos, oversized games, and a big indoor room with fireplaces when the weather turns.

Closed Tuesday, plus two to three weeks in January. Reservations hold nothing except the private room. No outside food. No dogs, no high chairs.

2711 Sound Ave, Baiting Hollow, NY 11933
Taproom and brew tanks at Jamesport Farm Brewery

03 · North Fork · Riverhead

Jamesport Farm Brewery

A 40-acre farm brewery with walk-up pints and first-come seating, plus shaded Hop Rooms that take 10 to 25 guests in two-hour blocks from May through August. New ownership arrived in 2025.

Beer garden, hop yard, a food truck every day it opens, and weekend music — the easiest landing spot for a crew that is not all drinking wine.

Closed Tuesday and Wednesday. No outside food. Limos and buses need a prior reservation and must arrive before 2 p.m. The weekend cover charge was dropped in 2025.

5873 Sound Ave, Riverhead, NY 11901
Ship-themed tasting bar at Jason’s Vineyard

04 · North Fork · Jamesport

Jason's Vineyard

A mythology-themed hangout with a ship-shaped bar, a picnic lawn, resident alpacas, and weekend live music around 1 to 5. Walk-in and first-come; six or more arriving with a hired driver must call.

One of the few rooms that still lets a crew eat its own food on the lawn — the picnic area allows outside food, though not outside drinks or coolers.

Snacks and cheese are sold on site. The flight price is not posted; older reports put it near $15 for four wines. Thin website and weather closures — call before a group drives out.

1785 Main Rd, Jamesport, NY 11947
Bocce court and lawn at Bridge Lane Tasting Room in Mattituck

05 · North Fork · Mattituck

Bridge Lane Tasting Room

Lieb’s value brand, and the most group-ready room on the fork: bar service, a six-wine flight for $20, and prepaid groups of 8 to 25 at $25 a head, capped at 25.

Rainbow picnic tables, an Adirondack lawn from April to November, bocce, shuffleboard, cornhole — and limos and buses are simply welcome.

Summer daily 12–7; off-season Thursday through Sunday. BYO picnic if you clean up, but no outside alcohol. The fruit is multi-region, so this is value drinking rather than a terroir tasting.

35 Cox Neck Rd, Mattituck, NY 11952
Red-roof tasting room at Pindar Vineyards in Peconic

06 · North Fork · Peconic

Pindar Vineyards

The largest winery on Long Island (Damianos, 1979): open daily 11–6 with walk-in five-wine flights, and public tours on Saturday and Sunday from May to October for $35 a person.

A deck, a pavilion, and a lawn big enough to absorb a crowd, with music Saturday and Sunday 1–5 and Sunset Fridays running about 4–8 in 2026.

A hired limo, bus, or van needs a prepaid time slot. BYO picnic outside in designated areas only — no outside food indoors, no outside alcohol. Weekend crowds are real. A second location sits in Port Jefferson.

37645 NY-25, Peconic, NY 11958
Grande Ole Osprey gazebo and lawn in Peconic

07 · North Fork · Peconic

Osprey's Dominion

A wide Main Road lawn with a gazebo, picnic tables, and cornhole, a walk-in bar, and Long Island’s first Carménère. A visitor report from October 2024 put four tastes at $18.

BYO picnic is explicitly allowed — uncommon now, and the reason a big group can eat here without a per-head food bill.

Call ahead for limo or bus groups. Live music on weekends in season. Loud and crowded on summer weekends, and the quality ladder is wide by design.

44075 Main Rd, Peconic, NY 11958
Lawn, gazebo, and vines at Duck Walk North in Southold

08 · North Fork · Southold

Duck Walk Vineyards North

The Damianos patio in Southold, over about 30 acres of Sauvignon Blanc, with any four wines for $18. Walk-in for small parties; six or more must reserve, and the reservation does not include a seat.

Light snacks are sold and BYO light snacks are allowed, reserved groups get a cheese platter, and music runs Saturday — Sunday too in season — from 1 to 5.

Do not confuse this with the Water Mill château. Hours pages conflict, so check before you drive. Music is typically May through October. Sweet and dry wines share one list.

44535 Main Rd, Southold, NY 11971

South Fork & the Hamptons

Only Duck Walk’s original Water Mill château scored strong for groups on this fork. It is a different address from Duck Walk North in Southold.

Château tasting hall at Duck Walk Southampton in Water Mill

09 · South Fork · Water Mill

Duck Walk Vineyards Southampton

The original 1994 Damianos château: $18 for four wines, reserves and dessert wines included. Walk-in for smaller parties; six or more must reserve by phone and buy the tasting.

A patio among the vines with Saturday and Sunday music 1–5, typically May through October — and the only South Fork stop on this list.

A reservation does not include a seat. Published hours conflict — call 631-726-7555. Light snacks are sold and BYO light snacks are allowed alongside purchased wine; there is no full kitchen. Not the same address as Duck Walk North.

231 Montauk Hwy, Water Mill, NY 11976

Group outing FAQ

Do we need a reservation for a group tasting on Long Island?

At six or more, almost always. Bridge Lane prepays groups of 8 to 25. Both Duck Walk rooms require a reservation at six or more, and it does not include a seat. Jason’s asks any group of six or more arriving with a hired driver to call, and Pindar sells a prepaid time slot to hired vehicles. Walk-up service stays first-come at Jamesport Farm Brewery and Riverhead Ciderhouse unless you booked a Hop Room or the Prohibition Room.

Which Long Island wineries allow a bus or a limo?

Bridge Lane welcomes them outright. Pindar requires a prepaid time slot for a hired limo, bus, or van. Osprey’s Dominion asks you to call ahead. Jamesport Farm Brewery takes them only with a prior reservation and only if they arrive before 2 p.m. Jason’s wants a call when six or more come with a hired driver. Everywhere else on the trail, assume no — the date-night estates ban vans on purpose.

How much is a group wine tasting per person?

Less than you would guess. Bridge Lane’s prepaid group rate is $25 a head, and its standard six-wine flight is $20. Both Duck Walk rooms pour any four wines for $18, and an October 2024 visitor report put Osprey’s at the same $18 for four. Pindar’s weekend public tour is $35. Jason’s does not post a price; older reports put it near $15 for four. The private rooms are priced as rooms: Long Island Spirits charges $250 for two hours in the Hidden Vault, plus drinks.

Where can a group book a private room?

Three places, in ascending size. Riverhead Ciderhouse’s Prohibition Room is a private two-hour tasting for up to 10, booked on Resy. Long Island Spirits’ Hidden Vault holds 11 to 20 for $250 per two hours plus drinks, up a flight of stairs with no lift. Jamesport Farm Brewery’s Hop Rooms take 10 to 25 in two-hour blocks from May through August. Twenty-five is the ceiling anywhere on this list — Bridge Lane caps its prepaid groups there too.

Can a group bring a picnic?

At four of the nine. Osprey’s Dominion allows it explicitly, Bridge Lane allows it if you clean up, Pindar allows it outside in designated areas only, and Jason’s picnic area takes outside food but no outside drinks or coolers. Both Duck Walks allow light snacks. Riverhead Ciderhouse and Jamesport Farm Brewery allow no outside food at all, though the Hidden Vault at Long Island Spirits accepts outside food and delivery.

Is Long Island good for a bachelorette party?

Only if you pick from this list. Bridge Lane is the natural anchor — buses welcome, a lawn with bocce and cornhole, and a flat prepaid rate — with Jamesport Farm Brewery or the Hidden Vault for a booked block. Several estates refuse the format outright: Rose Hill posts a no on buses and bachelorette parties, Sparkling Pointe will not seat an unbooked party bus, and Palmer and Paumanok turn away intoxicated arrivals.

Is the North Fork or the South Fork better for a group?

The North Fork, and not by a small margin — eight of these nine stops are there, most of them within a 20-mile run of Sound Avenue and Main Road. The only South Fork option is Duck Walk’s original château in Water Mill, which is a different address from Duck Walk North in Southold.