docks and houses on water
Greenport, NY harbor view

After a day of wine tasting, I can’t remember all the information imparted by Jo-Ann Perry of Vintage Tours, but one fact did stick with me. All 40+ wine makers on the North Fork of Long Island share an area smaller than one of Robert Mondavi’s fields in Napa.

Considering this tiny area, the variety and quality of wines produced on the North Fork of Long Island rival those produced on the west coast, and elsewhere. When you see Champagne by the glass priced the same as Paumanok’s Chenin Blanc in local restaurants, the reality sinks in.

The miserable weather of a rainy, cold day in mid-April could not dampen the enthusiasm of our small group as we traveled from winery to winery, tasting some of the best wines America has to offer. Jo-Anne set out empty wine boxes next to each seat on the van, “in case” we bought anything. After 4 stops, most of us had a case.

A weekend trip to Greenport is something that has long been on my to-do list, but the price of hotels in season has kept me away. $300+/night for the equivalent of a motel – or a romantic B&B is just not something I’m willing to consider. Even if I was traveling with a friend we would want our own rooms. My industrious stalking of the Harborfront Inn website finally paid off; they had a $149/night special for April weekends.

Greenport is almost at the tip of the North Fork of Long Island – it is the end of the line for the Long Island Rail Road. If Long Island was a fish, the Hamptons would be the bottom part of the tail and the North Fork the top. Not being a Hamptons kind of person, I like this characterization. It really is a quaint former fishing village yet completely modern age – with 2 inventive restaurants, many art and antique galleries, and one of the best curated wine shops I’ve ever visited. The presence of a Calypso of St Barth says it all. Relaxed and down-to-earth, but chic.


The 3 hour Long Island Rail Road ride to Greenport was painless. It’s about a 2 minute walk from the train to the Harborfront, but as warned, I couldn’t check in until 2pm. The very nice woman at the front desk (not cold or indifferent as mentioned on Tripadvisor) stowed my bags in the office and out I went.

Greenport was smaller than I pictured – and within an hour I had walked most of downtown. The town has some beautiful Victorian houses and New England-y churches. There are a lot of typical seaside tourist town stores; t-shirts, Vera Bradley and home decor items -and then some. Verbena had some funky jewelry, gift and decor items. A large IGA was a good place to buy a bag of North Fork potato chips for later. I managed to do to some damage at a store called Kharmah, that specializes in natural fiber, casual, comfortable clothing for women.

After making the difficult decision of what wine to buy for my room, with assistance from the owner of the well-stocked and very organized Greenport Wines, (Shinn Coalescence) I went to Noah’s for lunch.

Noah’s had so many tempting small plates it was hard to choose, but I opted for the Crispy Tasmanian Red Crab Tacos (how could I resist a name like this?) and a crab cake that was on a bed of perfectly julienned something. Not a slaw, but similar – with a hint of Dijon (as you can tell, I have no clue what it was, and it isn’t listed on their online menu!). Both were excellent paired with a glass of Bedell Chardonnay. I also had the very tart but tasty key lime pie. The place was surprisingly packed for a late lunch on an April Friday.

Since the wind was picking up – I decided it was time to check in to the Harborfront, which was literally across the street.

The $149/night rooms are the Superior rooms, on the first floor with a view of Greenport Harbor. My room was clean, lovely, with Frette bedding, down pillows, a very nicely designed bathroom. But do I really need a shower that comes with instructions? Unless it’s Laos and run by a car battery? Anyway, more on that later….

The view of the harbor and Shelter Island was excellent and I came to discover that unlike the hourly Fire Island ferries of my past, the ferry from Greenport to Shelter Island seemingly runs non-stop well into the night. I didn’t hear noise from the ferry, but it was there pulling in and out all day and night.


After breakfast at the Harborfront, I read for awhile until it was time for the 11:30am pick up by Vintage Tours. There were several other hotel guests in the lobby, including a woman in a black dress and 5″ heels, and I wondered if she was also taking the tour. Jo-Anne arrived promptly, loaded us up – and off we went to two other nearby B&Bs to pick up other guests. The woman in the heels went elsewhere.

Although after a day of wine tasting, I don’t remember the names of the B&Bs where we stopped, they looked interesting, and we got to see some of the smaller towns on the North Fork.

After Jo-Anne picked up the last couple, she gives us an overview of the day. All smaller wineries; she warned us that the first stop was somewhat unusual. Because I was the only person traveling alone, I was lucky to be sitting up front with Jo-Anne and got a private tour of the area. She has lived on the North Fork her entire life, knows everyone and is well connected.

Her tours make stops at 4 wineries and we pay for tastings. Unlike the day trip I took to the North Fork with Grape Getaways 2 years ago, there were no tours of the wine-making operation or vineyards. One tour is usually included, but the day is really about tasting, having fun and absorbing as much information a person tasting wine all day can hold.

As promised, the first stop was unusual. Water’s Crest is located in a strip mall in Cutchogue. The tasting room is about twice the size of my office cubicle. The wine making operation is in a large garage in the back. Jim Waters buys grapes from other growers, and makes wonderfully complex wines. He shows us the operation and explains the filtering system currently processing cider. I’m tempted to join the wine club, and buy my first 2 bottles of the day.

Next up – Shinn. The organic wine maker of the region, and the winery I most wanted to visit. The planned vineyard tour with Barbara Shinn is canceled due to the rain and cold weather, but Jo-Anne does bring us to the field’s edge to explain how the vines are pruned to prepare for the season. She also explains how grasses are grown to provide insects something to eat instead of the grapes. I think I’m remembering this correctly!

At Shinn we go into private room for the boxed lunch we previously ordered – and our tasting. There is a large group of women at another table celebrating something; the area is a great place for a birthday or shower and there are limos parked in every parking lot.

The Shinn tasting was a choice between 2 wines – 4 total. The couples all split their tasting so they try both. Since I was alone, the woman suggested two 1/2 pours. She would start me off with 1/2 a tasting, and come back with the other half after she made her way around the table. Unfortunately, she kept forgetting and leaving – and I felt ridiculous and petty chasing her around with my glass. But, I wasn’t missing the Boer Doe and 9 Barrels! I will definitely join this wine club. And, the sandwiches Jo-Ann brought from the Pipping Plover were excellent.

Next, we visited what seemed like the largest operation of the day, Peconic Bay. By this time, I was feeling the wine and all I can tell you is the place was packed, there was live music and I didn’t buy any wine. The wines were good, but not as exceptional as the prior two stops – and I did have to schlep whatever I bought back to NYC. By this time the people who would be driving home all had a case.

Luckily, I got a second wind in time to visit the Old Field. The Old Field is a family owned/operated vineyard and is noted for its mother-daughter wine making team. Perry, the daughter, conducted our tasting in what was a chicken coop. A wonderful setting and vibe – I loved this place! The wines were excellent too – and it was hard limiting the selection to two more for my box.

In the course of the day, some of us compared notes and discovered that we had all eaten at Noah’s the day or night before; and we were all planning to have dinner at the Frisky Oyster that night. A very nice couple – Linda and Bob from Connecticut – invited me to join them for dinner and we had a wonderful night of more wine and inspired cuisine. We split the Oysters Friskafella and crab cakes.

Like Noah’s, the menu had so many tempting entrees I had a hard time deciding and would have been happy with 2/3 the choices. Both Linda and I had the rack of lamb with mint fettuccine, which aroused my curiosity enough to select that dish. The lamb was perfectly cooked, but the fettuccine was a little oily. Bob selected a Lenz Gewurtraminer that paired well with our appetizers and entrees.


The sun finally returned, and my request was honored with an hour later check out time – noon. I went to the Coronet, an old fashioned diner known for their pancakes. The service was quick, the pancakes were huge, but they were just pancakes. Nothing special. I ate about 1/3 and went out to do last minute shopping and visit stores that I missed earlier in the week.

Doofpot, which had closed just as I was arriving the night before, is packed with gorgeous ceramics from primarily France and Italy. I love this sort of stuff but cannot buy another thing – my tiny apartment is packed full. I also visit the Artists Gallery, full of colorful Haitian art. Very tempted by a painting of mermaid, but I am in economizing mode, and already have wine to carry. Of course, the owner will ship! He gives me some of his cards and I promise to think about it. I’m still thinking…seriously.

After checking out and storing my luggage for a couple of hours, I sit in the park on the waterfront with my Kindle. Families come and go; the ferry comes and goes. I make one last stop for lunch – Bruce’s Cheese Emporium. How can a Deadhead not love a place with sandwiches named “Franklin’s Tower” and “China Cat Sunflower?” The roast beef and herbed havarti I select doesn’t have a Dead related name. Finally I go back to the Harborfront, and wheel my bag back to the train station, which is also the stop for the Hampton Jitney.

Unfortunately, the train from Greenport does not run on Sunday and the locals aren’t sure if the LIRR will resume service for the summer. The Jitney is the only option. All I can say about this trip is that just because a seat can recline all the way, doesn’t mean one should recline the seat all the way. I blame the Hampton Jitney for having seats that go back so far they literally bash the person in the seat behind in the knees. Not close like a plane, actually touching. I’m only 5’8″ – not sure how people with longer legs deal. The very nice attendant on the bus moves his ticket box off the seat so I can move.

The Harborfront is a lovely hotel, but it does have issues. If I was paying full rate, I would not be a happy guest. The sheets and towels are wonderful, but by the time I figured out how to get the shower jets to come out of the right place the first morning, the water was cold. And, I’m relatively good with complex shower instructions. The walls were thin – and a person in an adjacent room was walking back and forth, turning on and off the bathroom exhaust fan for hours. Very strange. In the middle of the night I was awoken by a loud banging noise from within the walls of the hotel, that repeated again at about 7am non-stop for 5 minutes, then dissipated. A local told me it was a pre-fab modular building, which makes sense.

The breakfast in the morning is decent, but it could be much better. A good selection of anemic looking pastry, muffins, bagels (not a browned top among them), fruit and yogurt. But, by 9:30 am every seat in the place was full – and this was off season.

Also, I would be curious to see where and how the vineyard workers live.


Long Island Rail Road offers very spotty service to Greenport. On weekdays there is a 9:13 train, and 2 trains at pm rush hour for commuters. There is currently no weekend service. Possibly service will increase for the summer.

Hampton Jitney – has regular service to the North Fork, including Greenport, 7 days a week.

Greenport Hotels on

The Harborfront Inn – is very well located for people without cars. There are also several B&Bs in town – and in the area.

Vintage Tours

Grape Getaways

Long Island Wine Country – Regional Website with map of Wineries


Long Island Wine Country

North Fork Living

Food Lover’s Guide to Long Island

Originally posted May 2, 2011




Long Island’s North Fork: The Perfect Car Free Trip From NYC