The North Fork of Long Island: An Autumn Getaway

Recently the New York Times noted that the American consumer is choosing experiences over goods, and scientists have found that experiences bring the most happiness, not a home full of useless goods. Richard E. Jaffe, a retailing analyst at Stifel Nicolaus, noted “the religion of consumption has proven to be unfulfilling.” (NYT, Stores Suffer from a Shift of Behavior in Buyers, 8/13/15) As the American consumer decides to spend their money on trips, eating out at restaurants, or socializing at bars, the retail industry has suffered with a 1.2 percent decline in sales at electronic stores through July and departments stores at 0.8 percent. So why is this important? Who cares? As you decide to take experience over purchasing another useless knickknack, let me guide you with some tips for travel through New England–and locations just a hair outside. This month and next, I will highlight seven locations to visit in New England and just outside the region. Here is number seven.


7.) The North Fork of Long Island, New York

Ok, so first on the list is not in New England. Now don’t judge too quickly, Long Island used to be part of Connecticut. In fact, it was so rural, early colonists in New York City looked down on those living on this long, sandy prominence of land. And also, truth be told, I have an affinity for Long Island having grown up there.


Autumn on the east end of Long Island is beautiful and serene, definitely worth the trip. Avoid the city and take one of the two ferries which leave from the Connecticut shore, either at New London or Bridgeport. I prefer The Cross Sound Ferry out of New London because I have been taking this ferry for the last thirty-one years, many times a year. Both are nice rides across the Long Island Sound, and they cut off hours of drive time and possible road rage that may erupt from having to skirt the edge of New York City across the Throggs Neck or Whitestone Bridges. The ferry itself is a nice relaxing ride across the water lasting an hour and a half at the most. Many of the ferries were landing crafts at Normandy Beach during WWII, and have been converted to the passenger and vehicle vessels we use today. If you decide to take the ferry, make a reservation, and be early for your appointed time, or you will lose your reservation. If you are really early, they will try to accommodate you on an earlier boat with no added fee.


Once you are on Long Island–we are going to assume from New London–you will arrive on Orient Point. After you get off the ferry and head west, the entrance to Orient Point State Park is immediately on your left. This is a beautiful sandy point, with a two-mile walk to a tip that stretches into Long Beach Bay. At the end of this peninsula is a lighthouse, which at low tide is almost accessible, and along the walk you may find old brick foundations which the salt waves lap against. Once you’ve walked around this point, head back to the Main Road, route 25, and turn west toward your next stop, Greenport Harbor.

10407218_699157440197059_3519969000783364820_nDecember run/swim


unnamedBug Lighthouse, Orient Point, NY

After you have shaken the sand from between your toes, slip on your sandals or sneakers and walk around Greenport Harbor to explore the kitschy shops, antique stores, and try some artisanal goods. When in downtown, you must venture into the Greenport Harbor Brewing Co., at their original brewery and tasting room in the old firehouse–a phenomenal brewery that knows IPAs are not the only beers to exist. Their Black Duck Porter is phenomenal and the Harbor Ale is a great well-rounded American Pale Ale. Once you have had your fill of the hearty brews, wander down to the famous Claudio’s where you can eat on the dock, sipping gin and tonics while slurping raw oysters, or sit in their dining room, flanked by dark wood and lead pained glass. Don’t neglect the carousel in the park along the waterfront, which once was at Grumman Aircraft Corporation, and explore the large camera obscura which is one of five in the United States and of fifty in the world. Now that you’ve had your fill of this once busy shipping port, again direct your vehicle west on the Main Road, route 25, and enjoy a leisurely ride.

12019944_10207571577398667_5746390696907936793_n Black Duck Porter!

Driving down the road you will be flanked by marsh land and open bays. Along the way you might find little farmsteads peddling locally grown vegetables, pumpkins, and cornstalks. But next on our stop are the many wineries. Along the North Fork there are thirty-three wineries, which prices can range between five to twelve dollars for a tasting. A few of my favorites are within Southold and Cutchogue–my home town. Croteaux Vineyards at 1450 South Harbor Road, Southold, is a spectacular winery with a wonderful old world feel, and serene view of grape vines stretching long across dark humus fields. Their specialty is Rosé, and they do it well. Lightly sweet, crisp blushes, add to a wonderful evening as the sun sets into the horizon, blazing reds and purple across the twilight sky. Get a cheese plate and a bottle, and enjoy the crisp rustling leaves blowing across the ground.


Only a few miles down the Main Road is Pindar Vineyard. This has been a staple in my family for years, and I always recommend this winery. Pindar has it all. From blushes to whites, reds to ports, late harvest gewürztraminer to rieslings, they seem to have a handle on making good wines. The atmosphere is perfect with large exposed wooden beams inside a great room, where two rectangular bars are the centerpiece, while their wines are lined up against the wall for purchase. During the summer, fields of sunflowers, their large seeded yellow heads bulbous and heavy, litter the grounds around the winery. Right across the street is Farmer Mike’s Farm-stand, which has been open for over thirty years, a great location for local brussels sprouts and potatoes. Fall in full swing, the pick-your-own pumpkin field to the left is brimming with vines and bursting orange globes, snaking around the rows of black earth. So after a day of wine and beer tasting and wandering the streets of Greenport, to dinner we go.

12032057_10207571617559671_5081417069081940850_nPindar Winter White and Mythology

In Cutchogue there is a little unassuming pizzeria called Michelangelo’s in a shopping plaza next to the King Kullen Supermarket. This little restaurant is inconspicuous and seems plain from the outside, but if you want great Italian food, and some of the best pizza around, then you better make a reservation for dinner, because if you don’t, you will not make it into the back dining room. The cozy atmosphere of this small family dining establishment is limited, but a wonderful experience that will leave you satisfied. On your way out after dinner, grab a slice of the chicken parm pizza for later, or maybe a slice of the white. If you aren’t in the mood for Italian, try the Birchwood of Polish Town, only twenty minutes away in Riverhead. The Birchwood has been a staple in this community for over three decades, and the decor of their restaurant is a mix bag of interesting epherma–they are quirky without trying. Beneath all the decorations is dark wood which shines under the tavern lamps. Their food is delicious Polish food, and I recommend the pu-pu platter, which can easily feed four to five for appetizers, with regular appetizers mixed along side polish fair. A must if you love pierogis, golumpkis, and kielbasa.

What about desert? Well that is easy. Magic Fountain in Mattituck is the place to go. With some of the richest, creamiest ice cream, their selection is astounding, and the homemade, icy, sweet treat is sure to please every time. Try the cookie monster, sapphire blue in its splendor, or the cookies and cream which is a grey hue due to the amount of Oreos that grace the mix. Take your ice cream and party down the block, directly across from this ice cream stand, to the water. Sit on the beach or skip stones into the bay, as the lights twinkle across the Peconic on the South Fork.

For those of you who love shopping, the Tanger Mall is in Riverhead with stores such as Off Saks Fifth, Banana Republic, J Crew, Nike, Pottery Barn, and so on, with over a hundred stores in the three different plazas. If you are not looking for food, drinking, or shopping, there are always the many corn mazes and recreation villages of traditional farming and colonial living on Long Island.


The North Fork of Long Island has much to offer, and I recommend at least spending four to five days there. There is much to do, see, and experience. Also, if you have the time, you can always take the ferry to Shelter Island, and zip over to the South Fork where windmills from Dutch times still litter the landscape. Keep in mind there are no fast food restaurants on the North Fork of Long Island so if that is your thing, you are out of luck. There is a McDonald’s in Mattituck, but due to zoning which restricts restaurants, they have no drive-thru window and the building looks like a house. Also, if you are one of those people who looks for Starbucks, the only one is in Mattituck in the shopping plaza. Coffee on Long Island is served in little delis and is tongue searing, roof of the mouth burning, skin melting radioactive hot. And it is not local, or artisanal, but usually Chock Full o’nuts. Even Dunkin Donuts is almost nonexistent.

224265_1039340354896_2923_nWindmill, Southampton, NY

From Orient to Riverhead and back, the North Fork is a place to unwind, enjoy the fall, drink some wine and good ales, eat good food, and walk the many beaches that encompass this beautiful peninsula. There is so much more to see and many vineyards and breweries on the North and South Forks which I did not mention. There is only limited space to talk about an area, so get on the internet and search for what interests you. Also, if you are a fan of Orange is the New Black, the flashback Piper has when she is sneaking into the movie theater and sees her father, well that movie theater, The Suffolk, is on Main Street in Riverhead. So get a quick pic out front under the bright neon lights.

223305_1039340314895_2504_nThe Big Duck, Flanders, NY

226295_1039340234893_1652_nAbandoned farm stand


Bayard Cutting Arboretum

Note: Greenport Harbor Brewing Co. now has a tasting room on the Main Road, Peconic, NY. The Peconic location is a larger location with outdoor seating. Both has great character and charm.

Long Island Wines

Greenport Harbor Brewing Company





David Jester

About David Jester

David Jester lives in the Midcoast region of Maine. He received a masters degree in American and New England Studies from the University of Maine. David is a full-time firefighter/paramedic and writer, who maintains another blog He travels the world, but chooses locales that many would never consider for vacation. The world is full of many different and unique places, why not see them all?