Long Island’s Beautiful North Fork

As the temperature begins to drop, the urge to embrace the season with farm stands, pumpkins, apples and vineyards set in.

This post was originally written in 2017, remember those pre-COVID days?  Well, happy to report all is not over on the North Fork of Long Island.  The vineyards are welcoming visitors, just not huge bus loads of party animals which may be more enjoyable in fact.  The sunflower fields in Riverhead, pumpkin patches, and farm stands are open for business, just requiring that you wear a mask when indoors.

I recently had the exciting experience of celebrating birthdays with some friends on the “Wine Wagon”.

With a limit of 10 people we met up at Osprey Dominion winery for snacks and some live outdoor music.  Soon Gary pulled up with the wagon and we lovely ladies boarded a seat at the wagon counter and placed our feet upon the pedals.  We were off down the road to our first adventure.  Of course, we were in for a bit of a surprise when Gary alerted us that by law he had to turn off the engine on the road, and it was up to our pedaling efforts to get us to the next location.  

At our first stop, we remained on our wagon and were served a choice of 4 different vintages.  After one hour, we headed on back to the main road this time with someone’s iphone blasting country music.  As we passed the local animal shelter, we met a man walking down the street with a puppy.  We invited him to join us and sang to the puppy until our new friend had had enough of us.  

At the next vineyard, we went inside with our masks, ordered small glasses of wine to taste and sat outside to enjoy the beautiful sun on this fall afternoon.  As the sun went lower in the sky we took some final photos and boarded the wine wagon with Gary to head back to our starting point.   Indeed, a good time was had by all and maybe we even burned a few calories with exercise?



Drive east on the Long Island Expressway until the end, then take route 25 east through Riverhead.  On my last visit, we had the app WAZE turned on and took some back roads to avoid traffic in Riverhead.  It did not save much time, as it still took almost 45 minutes to drive the 12 miles to the first vineyard.

We stopped at a delightfully colorful farm stand with painted antique tractors, gigantic pumpkins, pies, bread, local honey, roasted corn and ripe tomatoes like my dad used to grow.  After filling some bags with tasty treats we got back on the road and headed towards the vineyards.

Considering the traffic was so slow, we stopped at the first one.  Paumanok Vineyards is conveniently located just off the main road and has a wide variety of wines available in the tasting room ranging from $8 to $20 per person to taste 4 samples.  The tasting fee is credited toward a purchase of a bottle so that is an incentive.

What I loved about Paumanok was that they were offering oysters outside on the deck.  It is a very pretty location but they do not allow you to bring your own picnic foods.


Next on our self guided tour, we stopped at a small vineyard called Sherwood House Vineyards. This was different as it was a small and cozy farmhouse with a quaint fireplace and bar and the size alone did not welcome larger tours.    Again outside food is not permitted, so we took our picnic basket and continued onward.


Macari Vineyards has opened another location on Main Road in Cutchogue as well as the original location in Mattituck.  The Macari family started growing grapes on a 500 acre former potato farm in 1995.  The family boasts an ecological and holistic approach to the soil which includes a complex composting program and a herd of Long Horn cattle.

By this time we had eaten our picnic lunch in the car and no longer asked if we could eat inside.

Next stop was the Pellegrini Vineyards in Cutchogue.  We had been heading here initially because they had posted on the website to have live music.  Not only did they have live music, but we did bring out some cheese and crackers and had decent size small cups for our 4 tastings at $12.  The wine was good and the sunshine was terrific.  We even saw one of the common sightings out east – a bachelorette party!


Since we were close to the end, of the North Fork, we kept driving to visit Orient Point.  The ferry to Connecticut had just arrived and several cars were exiting onto the only road east. We took pictures and speculated about the mysteries of Plum Island that we could see from the beach.  Did you know that Plum Island was originally established by the Army to protect livestock from diseases, such as the study of foot-and-mouth disease in cattle.  Apparently there has been some controversy over the safety of the facility and the author Michael C. Carroll wrote a book called Lab 257  alleging a connection between Plum Island Animal Disease Center and the outbreaks of West Nile virus, Lyme disease  and duck plague.   Makes you wonder…


But not for too long, we started heading back home but ended up on the north road, County Road 48, so we stopped at Sparkling Pointe Vineyards and Winery in Southold.  This vineyard plants only the classic Champagne grape varieties, so if you like Champagne, this is the place to go.  The tasting house is large with high ceilings and light.  In the gift shop are Brazilian costumes that the owners have worn in Brazil during Carnaval so a unique experience is enjoyed at this location.

After a fun afternoon, we were once again hungry and found the best place nearby to purchase fresh seafood: Southold Fish Market on Main Road in Southold.  You can eat inside or out and there is a bar that serves drinks as well as oysters! We took some fresh striped bass home to cook later and it was amazing.

Not to be missed on a trip to the North Fork would also be a visit to the quaint village of Greenport.  Although important for the fishing and whaling industry in the past, it now entices tourists with adorable shops, good restaurants and a carousel from the 1920s.

If shopping for name brand items is your thing, you are in luck as Tanger Outlets is located at the end of the Long Island Expressway and features so many great retail stores.

Being a local Long Islander I have had many visits out east over the years.  I must also include a favorite vineyard I visited with my book club several years ago in Baiting Hollow.  Baiting Hollow Farm Vineyard is special and if you only have one place to visit I would highly recommend seeing this vineyard.

The tasting house is large, there is plenty of outdoor seating and you can bring your own food. In addition I have been there 3 times and always enjoyed live music.  The best part is that the vineyard has a rescue farm for horses.  Horses whose lives were at risk are brought here for a peaceful sanctuary and a second chance.  You can support their horses and learn more by logging onto their website and view the beautiful animals.

Don’t we all deserve a second chance?  Thanks for reading.

tour eastern Long Island New York wineries

16 Responses

  1. Sounds like it was a beautiful day! I appreciate how you included the horse sanctuary too. We all deserve second chances!!

  2. That’s a nice post. Your pictures are beautiful. The picture of the table with the bottle of wine, the two glasses of wine and oysters on it caused my mouth to water. I could smell the bouquet coming through my computer screen.

  3. I didn’t know there were vineyards in that part of the country. Definitely on my list of places to visit!

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Runaway Widow
Join me, Kristin, on my journey to adjust to the sudden death of my husband and learn to live as a young, middle-aged, remarried widow.

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