East End Pumpkin Picking: Off the Vine or Off the Stand

Did You Know? In the mid-1970s, a North Fork high school student named Al Krupski noticed that nobody around him was growing pumpkins. He planted some anyway. The October pumpkin field is now one of the things the East End is known for, and Krupski Farms in Peconic is still in the family, five generations deep.

Yes, there are East End farms where you walk into an open field, find a pumpkin still attached to its vine, and take it off yourself. Most of them sit in a band that runs from Riverhead east along Sound Avenue and onto the North Fork, with a second cluster around Water Mill and Bridgehampton on the South Fork. Everywhere else out here, Shelter Island and Montauk included, the pumpkins come to you already picked and stacked at a farm stand.

Both are good days. They are just different days. A vine patch means boots, a wagon, and twenty minutes of walking rows before anybody agrees on anything. A stand means you pull over, pick one off the pile, and are back in the car in five minutes with cider donuts. Knowing which one you are driving toward is most of the trick.

Start with the kind of pumpkin day you want.

Cut it off the vine – open fields where the pumpkin is still growing when you find it, concentrated in Riverhead, on the North Fork, and around Water Mill.

Take it off the stand – pumpkins the farm picked for you, stacked out front, which is most of the East End in October and the only option on Shelter Island.

Ask before you drive – a few places arrange picked pumpkins in a field for photographs, which looks like a patch from the road. A quick call settles it.

Stay the night – Saturday afternoon is the busiest stretch of the season at every patch out here, so the easier version of this day starts the evening before.

Jump to a Region

The guide runs west to east, the way most people arrive. Montauk has no pumpkin patch of its own, so it comes in through the South Fork stands and the routes in Make a Day of It.

• Riverhead – the longest run of vine patches, most of them on Sound Avenue
• North Fork – old pumpkin ground, two open fields, and farm stands the whole way out
• Shelter Island – no patch, good pumpkins, and a ferry ride to reach them
• South Fork – a tight cluster of u-pick farms around Water Mill and Bridgehampton
• Make a Day of It, or Stay the Night – three routes with somewhere to end up
• Before You Go – what to bring, what to ask, and when to go
• Pumpkin Questions, Answered – quick answers for planning the day

Riverhead

Sound Avenue is the reason this region has more pick-your-own pumpkins than anywhere else on the East End. The road runs east out of town past one farm entrance after another, and in October the fields on both sides are orange. You can do two patches in a day here without working at it.

Where can you pick pumpkins off the vine in Riverhead?

Yes, and this is the easiest part of the East End to do it. Running west to east: Lewin Farms in Calverton, Holzman’s Family Farm and Harbes Orchard in Riverhead, Helen’s Flower Farm and Stakey’s Pumpkin Farm in Aquebogue, and Harbes Farms in Jamesport all grow pumpkins in open fields and send you out to cut your own. Each farm sets its own patch days, so check the farm’s website before you go.

Lewin Farms, Calverton – The westernmost of the group, a large family farm where pumpkins are one crop among many you can pick yourself. The fields close earlier than the stand does, so this is a morning stop rather than an afternoon one. Roasted corn and a weekend corn maze round it out.

Holzman’s Family Farm, Riverhead – A smaller Sound Avenue farm that leans into the whole afternoon: pumpkins on the vine, corn and hay mazes, barrel rides, a sunflower walk, and pumpkin decorating for the kids. Leashed dogs are welcome, and you are invited to bring your own picnic, which is not something every farm says.

Harbes Orchard, Riverhead – Nine acres of on-the-vine pumpkins further east on Sound Avenue, paired with apple picking on the same property. Add a corn maze, pony rides, and music on weekends and it becomes the full festival version of the day. Harbes runs three East End farms and this is the one where apples and pumpkins share a parking lot.

Helen’s Pumpkin Farm, Aquebogue – A Union Avenue farm that works both ways: a field you can pick from, and picked pumpkins waiting at the stand for anyone not in the mood to walk one. Helen’s runs greenhouses and a flower farm on the same ground, so the fall stop tends to end with mums going into the car alongside the pumpkin.

Stakey’s Pumpkin Farm, Aquebogue – Farmer Jim is a third-generation farmer and the first in his family to open a pick-your-own field. It started at just over an acre in the mid-1970s and now runs to twenty-six acres holding eighteen varieties, all of it cut off the vine. There is a corn maze, a country store, a flower house, roasted corn, and hay rides, and the family is open about wanting to keep the ground farmed rather than developed. No pets.

Harbes Farms, Jamesport – The last one before the fork proper, with nine acres of on-the-vine pumpkins, a corn maze, and hayrides that run out around the pumpkin fields. Of the three Harbes farms this is the quieter one, which is the whole reason to pick it over the other two on a Saturday.

Local Tip: These six sit close enough together that two in one morning is realistic. Take them in the order above and you finish pointed at the North Fork.

Where can you buy Riverhead pumpkins already picked?

Every farm above also stacks picked pumpkins near its stand, so you can skip the field entirely and still buy from the farm that grew them. Helen’s Pumpkin Farm is the clearest example, with a patch and a stand running side by side. If you want the stand without the field at all, Briermere Farms sells pumpkins alongside everything else the season is putting out.

Briermere Farms, Riverhead – A Sound Avenue stand people drive out of their way for, known for fruit pies made on site. Pumpkins come out with the rest of the fall produce. There is usually a line, it usually moves, and the pies are the reason.

Local Tip: Whatever you came for, leave room in the car. Mums, cornstalks, and cider tend to be stacked right where you exit.

North Fork

Route 25 and County Road 48 run the length of the fork, and between them the farm fields alternate with vineyards and old barns. This is where East End pumpkin growing started as a commercial crop, and a few of the farms out here have been at it long enough that the pumpkin field is part of the family story.

Which North Fork farms let you cut a pumpkin from the vine?

Two, and they sit about fifteen minutes apart. Harbes Family Farm in Mattituck comes first heading east and grows its patch on the vine, then Krupski Farms in Peconic. Both open fields and send you out to pick your own. Everything else on the fork sells pumpkins already picked, so plan around these two if picking your own is the point of the drive.

Harbes Family Farm, Mattituck – Eight acres of on-the-vine pumpkins, and the most built-out of the three Harbes farms. The Barnyard Adventure play area is the draw for younger kids, and the farm market sits across the road with roasted sweet corn going all day.

Krupski Farms, Peconic – The farm from the callout above, and still the one people mean when they say they are going pumpkin picking on the fork. The family works more than fifty acres across three fields, with a smaller u-pick field you walk yourself, and grows more than thirty varieties between pumpkins and squash, which is why the stand looks the way it does in October. There is a corn maze and a haunted barn, leashed dogs are welcome, and the painted jack-o’-lantern on the side of the building has been a landmark on Route 25 for years.

Where can you buy a North Fork pumpkin without walking a field?

Almost anywhere. The Harbes market in Mattituck and Wickham’s Fruit Farm in Cutchogue both sell picked pumpkins at the stand, and by October most of the farm stands along Route 25 and County Road 48 have them out front. This is the easy version of a North Fork pumpkin: you are never more than a few minutes from one.

Wickham’s Fruit Farm, Cutchogue – A family business going back roughly one hundred seventy years, and the stop that makes the strongest case for skipping the field. The pumpkins are sold at the stand rather than picked, and what you come for is everything around them: cider donuts out of the fryer, the orchard, and one of the oldest working farms on the fork. It also appears in our apple picking guide, because the orchard is the other half of the same trip.

Local Tip: Harvest weekends put pumpkin traffic and tasting room traffic on the same stretch of Route 25. County Road 48 runs parallel to the north and is usually the faster way back.

Shelter Island

Here is the honest version: there is no pick-your-own pumpkin patch on Shelter Island. An island this size, reachable only by ferry, supports farm stands rather than corn-maze operations, and the ferry ride is a real part of the day rather than an obstacle to it. The pumpkins are good, they were grown a few fields away, and you will be back on the boat before the kids get restless.

Where do you get a pumpkin on Shelter Island?

At a farm stand, and it is worth the crossing. Sylvester Manor Educational Farm sells pumpkins, gourds, and squash through the fall, and the smaller roadside stands around the Island put them out as the summer produce winds down. Take the North Ferry from Greenport or the South Ferry from North Haven, and plan on the stand being your stop rather than a patch.

Sylvester Manor Educational Farm, Shelter Island – A working educational farm on grounds that have been continuously farmed since the sixteen hundreds, with a timber-frame farm stand the community helped build. In fall the stand fills with pumpkins, gourds, squash, and cider alongside woodland-raised pork and baked goods from East End bakeries. Hiking trails on the property are open daily, which turns a pumpkin errand into an afternoon.

Local Tip: Build the ferry into the plan rather than around it. Greenport to Shelter Island to North Haven turns a two-fork pumpkin day into one loop instead of a long backtrack.

South Fork

The South Fork grows fewer pumpkins than the land west of the canal, but what it has is concentrated. Four vine patches sit within a few minutes of each other around Water Mill and Bridgehampton, close enough to the ocean that you can pick in the morning and be on the sand by the afternoon.

Is there a real pumpkin patch in the Hamptons?

Yes, four of them, unusually close together. Running west to east: Hank’s PumpkinTown, The Milk Pail and Seven Ponds Orchard in Water Mill, then Fairview Farm at Mecox in Bridgehampton. All four send you into the field to pick your own, and The Milk Pail grows its pumpkins on the vine. Days and seasons vary by farm, so check each one’s website.

Hank’s PumpkinTown, Water Mill – The largest fall operation on the South Fork, run by the Kraszewski family, with pick-your-own pumpkins across a substantial share of the farm’s acreage. The farm’s own advice is to come earlier in the season if picking your own is what you are after, since the field thins out as fall goes on. Beyond it there is a maze park built for kids, apple picking, wagon rides, and gem mining, plus hard cider made by the next generation of the family for the adults waiting at the end of it.

The Milk Pail, Water Mill – A family farm going back generations, where more than sixty varieties of pumpkins, squash, and gourds are grown on site, from miniatures to specimens over a hundred pounds. You pick apples from dwarf trees sized for small children and pumpkins from the vine, then finish at the market for cider and doughnuts.

Seven Ponds Orchard, Water Mill – A working orchard where the pumpkin field is one stop among several. Apples, berries, and sunflowers are all pick-your-own in season alongside the pumpkins, so a run here tends to turn into a full basket without anyone planning it. Hay and tractor rides tour the fields.

Fairview Farm at Mecox, Bridgehampton – The easternmost of the four, the Ludlow family farm, sitting on high ground above Mecox Bay. Pumpkins, gourds, and squash come out of the field, and the eight-acre corn maze is what brings people from both forks: roughly two miles of paths, stalks ten feet tall, and two bridges with views over the farmland toward the water. Raw milk cheese is made on the farm from its own Jersey cows, and the stand’s pies are worth the stop on their own.

Local Tip: Four vine patches inside a few minutes of each other means you can actually be choosy here. Start at the one furthest from the highway and work back.

Where do you buy a South Fork pumpkin without picking it?

At a farm stand, and east of Bridgehampton that is the only option, since there is no pumpkin patch out that way. Balsam Farms sells at its Amagansett stand and stocks its Montauk market with the same produce, which makes it the closest thing to a Montauk pumpkin.

Balsam Farms, Amagansett – A farm started in 2003 by two Cornell friends and grown into two retail stops, the original Amagansett stand and an indoor market in Montauk. Fall brings pumpkins out back alongside the last of the season’s vegetables, and the Amagansett stand keeps pull carts by the door. If you are staying in Montauk, this is the pumpkin run that does not require driving west.

Local Tip: Pick in Water Mill in the morning and you can be watching the light go down at an ocean beach by late afternoon without rushing any part of it.

Make a Day of It, or Stay the Night

Three routes that pair a pumpkin field with somewhere to eat and somewhere to end up.

The Sound Avenue Run

Start west and work east. Two patches in the morning, a stand stop for pies and cider, and lunch in Riverhead. Spend the afternoon on the North Fork and stay the night in Greenport or one of the hamlets along Route 25. Sunday is for the drive home with the back of the car full.

The Ferry Crossing

Pick on the North Fork in the morning, take the North Ferry from Greenport to Shelter Island, and stop at the farm stand there before crossing to North Haven on the South Ferry. Dinner in Sag Harbor, a night on the South Fork, and the Water Mill patches waiting the next morning.

The Water Mill Loop

Four vine patches within a few minutes of each other, an ocean beach fifteen minutes south, and Montauk another forty minutes east. Pick in the morning, beach in the afternoon, and stay out on the point where the season is quieter than it was in August.

All three fit an overnight better than a day trip. Saturday afternoon is the crowded stretch at every patch on the East End, and a Sunday morning field is a different experience entirely. Staying over is how you get it.

Where to Stay: Find places to stay across the East End

Before You Go

• Check the farm’s own website before you drive. Patch days, seasons, and admission rules differ from farm to farm, and some open the field only on certain days.
• Ask how the pumpkin gets cut and carried. Some farms hand you cutters and a wagon, some sell by weight at a scale, and some have their own rule about twisting rather than cutting.
• Wear boots you do not care about. A working pumpkin field is dirt, vine, and mud after rain.
• Confirm the pet policy first. Some patches welcome leashed dogs and some do not allow them at all.
• Go early in the day, and early in the season. Weekend afternoons are the busiest hours out here, and a pumpkin field is a crop like any other: the longer fall runs, the more of it has already been carried off. If cutting your own is the whole point of the trip, the front half of the season is the safer bet.
• Bring cash. Not every farm stand out here takes cards, especially the smaller ones.
• Leave room in the car. Cider, donuts, mums, and cornstalks are usually stacked right by the exit.

Pumpkin Questions, Answered

The Long Way to a Pumpkin

You can buy a pumpkin anywhere. That is rather the point of them. What the field gives you is the part nobody can sell at a checkout: the walk out, the arguing over which one, the vine still attached when you find it, the weight of the thing as you carry it back across a farm that has been growing them since before you were born.

The pumpkin on the porch in November looks the same either way. You will remember which kind it was.

Traveling without the kids, or after they have gone to bed? Our East End wine harvest guide covers grape stomps and fall tastings on the same roads, often at farms a few minutes from the pumpkin fields.

Find Your East End.