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Have You Seen Greenport Lately?

Originally Posted: April 16, 2009

Andrea Aurichio

  |   11 Comments · Print Article

Hot wheels on the dock outside Prestons. The creation of Mitchell Park was the shot in the arm that provided the much needed impetus to galvanize long talked about plans to rejuvenate the seaside port as a tourism destination that would rival Sag Harbor, its sister whaling village across the bay. Photos by Andrea Aurichio and Christine Bellini

Claudio's Dock is a popular spot for harbor watchers where the Shelter Island Ferry plies the waters every 20 minutes and pleasure boaters cruise to the Village.

Greenport - For those who predicted for years that Greenport is the up and coming destination to rival the likes of Sag Harbor, you may now take a bow. This sister harbor village had all the markings of a weekender's paradise but for years was over shadowed by the trendier villages of The Hamptons. No more.

The phrase "you don't have to go far to get away" has become the welcoming message of Greenport where things are now hopping all year long. This seaport village has transformed into a truly fascinating blend of seafaring charm and on-trend happening as Front Street takes center stage.

There is always something to do in Greenport these days where boutiques and art galleries are flourishing along with the family-friendly carousel, skating rink and a camera obscura all located in Mitchell Park on Front Street directly on the harbor. Starbucks has established a beachhead on Front Street that survived the economic downturn that forced the coffee chain to close stores on Long Island and elsewhere around the country.

The park, once the site of Mitchell's Restaurant and Marina, fell into ruin after the landmark restaurant was destroyed more than three decades ago by one of the most dramatic fires in Village history. The restaurant owned and operated by the Mitchell family featured an impressive wooden bar that dominated the center of the large dining area enabling patrons to sit around all four sides while bartenders worked in the center of the square. The marina hosted dozens of large yachts in its heyday. Locals and tourists alike spent many a summer evening going down to the docks to take a fanciful look at the boats before stopping for ice cream at the now defunct Paradise Sweet Shop.

Mitchell's was a hub for diners and boaters who flocked to its doors. The restaurant hosted the Lions Club and the Rotary and also accommodated large parties for summer residents during peak season. "See you at Mitchell's" was a classic greeting exchanged among friends when they met on the street in the city before heading out to the East End. When the Mitchell family closed their business they left a gapping hole in the heart of the Village.

The Carousel is now synonymous with Greenport Village despite early opposition to the merry-go-round acquired from Grumman's in Calverton.


It took years to revitalize the four-acre site closed off from the public by a chain link fence that kept trespassers off the property as the restaurant building deteriorated villager's eyes before it was razed to the ground. That eyesore eventually transformed into a park that is the jewel in the crown of Greenport today where people gather for concerts or take a lunch break as they gaze across the harbor to Shelter Island's shorefront.

The Harbor Front Inn took tourism in the Village to another level providing upscale rooms with harbor views and Internet access.

The impetus to develop the site and create Mitchell Park came in the unlikely form of a carousel given to the Village by the Calverton based Northrop-Grumman Corporation. Former mayor Dave Kapell, a real estate broker, piano dealer and carousel buff, gladly accepted the gift. The carousel became synonymous with Greenport as the Mayor installed his twirling, whirling go-round in a Morton style building on the corner of Front Street next door to the movie theater.

Moviegoers complained the carousel music interfered with sound in the movies drowning out the dialog of the actors on the screen. The pro-carousel faction pointed to the increase in foot traffic in the village created by the entertainment the carousel offered to local children. Kapell's pet project was controversial to say the least.

The problem was eventually solved when village officials embarked on a nearly world-wide search for architects willing to participate in a competition aimed at finding the best design for Mitchell Park. The plans had to include a pavilion to house the antique carousel built in 1924. Village officials also wanted to create a walkway along the harbor's edge providing pedestrians with direct access to the waterfront.

They succeeded. The carousel is open in the summer and protected in its pavilion during the winter when it is not in use. An ice skating rink provides inexpensive winter recreation to the general public and the curious camera obscura serves, also at the waterfront park, is employed as an instructional tool useful in acquainting visitors with the origins of the camera while proiding a bird's eye view of the entire downtown.

The Frisky Oyster has made its mark on the Village with its own brand of dining that is so popular reservations are required even in the winter months.


Restaurants rarely close for the winter these days in this now thriving village. The Frisky Oyster, a trendy upscale eatery, eventually replaced the Sweet Shop after several other attempts to fill the void with a new food establishment failed. The success of The Frisky and other establishments around the village, where home sales soared at record prices until recently, highlights the progress made by the business community to save their Village by embarking on that revitalization plan. Although the plan had many false starts as empty storefronts and derelict houses characterized the Village for years, the last decade has given rise to a dramatic change in Greenport as the beleaguered often ridiculed community reestablished itself as a destination point. Greenport is now the place to go on a summer evening or a rainy day. It is also a place to do your holiday shopping or take your out of town friends on a local tour.

The transformation of the vintage 1950's classic Greenporter Motel, once owned by the Levin Family into an upscale South Beach inspired motel attracted praise and criticism among village residents who still point with wonderment to the spare white exterior. Further down Front Street, a former strip mall between the movie theater and the post office was torn down and replaced by the upscale Harbor Front Inn, that features designer decorated rooms with harbor views and Internet access. This walk to all spot is easily accessibly from NYC by train and bus. The LIRR stop and the Jitney pick up and departure are a short walk from the Shelter Island Ferry terminal.

The Greenporter was transformed from a 1950's motel to a South Beach inspired operation known for its breezy décor and wine bar.

The seaport village has retained its heritage as a whaling and shipbuilding center that rivaled the whaling ports of Sag Harbor and Nantucket and New Bedford. The whaling industry was replaced by commercial fisherman who held sway in the village until the 1950s. Today, yacht yards and marinas geared to recreational boaters carry on the seafaring tradition. Sailboats abound in the waters around Shelter Island where world-class sailors rule the day as they race around the Island in Monday night and Wednesday night races. It's great entertainment and its free once the season starts.

Claudio's Restaurant and Clam Bar provides an ideal dockside vantage point for anyone who wants to watch the harbor traffic or the races as they eat some fresh clams on the half shell.

If you live in Sag Harbor, take the ferry to the north side of the Island then hop the second boat to Greenport as a foot passenger to save on the fare. Once you set foot on the Greenport shore you will find yourself in one of the best walking villages on the East End. The village street, laid-out in a logical pattern, form an organized grid making it nearly impossible to get lost. You can always follow the North Fork rule: "turn around and head back when you hit the water." You will see vintage homes from the whaling days built in the 1830s when the Village was incorporated as well as the earliest homes built around the 1640s when the area was first settled.

This distinctive community floundered around adopting several names before "Greenport" took hold. The Village was settled in the mid 1600s by colonists from New Haven, CT. The Village was called Winter Harbor before the Revolutionary War. After that, the enclave was called Sterling, a reference to Lord Sterling. Then residents referred to the community as Greenhill until finally selecting the name Greenport when the village was incorporated in 1838.

Claudio's Clam Bar specializes in outdoor dockside dining once the season starts.


A visit to Greenport is a great day trip that can include a stroll around the village, a stop for lunch at one of its many new and well-reviewed hot spots dockside, and a visit to the Railroad and Maritime Museums located near the ferry terminal directly on the harbor. Shopping is an event as moderately priced and stylish shops compete side by side with trendy Calypso and Mint, upscale boutique operations with multiple locations. The Arcade Department Store packed with merchandize from floor to ceiling is a call back to to the days of the true five-and-dime. This store has it all from beach towels to pots and pans to souvenir mugs that read "Greenport". For lovers of all things ships and sea a visit to Preston's on the dock is a must. The harbor front emporium sold supplies to the Vanderbilts and the Astors during their sailing days. Tales of America's Cups past and present abound around here where the serious sailors congregate.

The Rumbline remains a popular gathering spot many years after its establishment by Robert Copas, an avid sailor and resident of East Marion.

For those who want to spend more time in Greenport as they tour the East End, the Village has two outstanding boutique motels on Front Street. The Greenport Inn has 30 rooms and is located on the landside of Front Steet while The Harborfront Inn is directly on the harbor as its name suggests. The 35-room establishment offers rates as low as $169 a night and features several off season events aimed at introducing visitors to the North Fork's wine region. The Harborfront offers a Grape Escape and a Crush Course for those who want to tour the region's wineries for a few days. The Grape Escape will run approximately $499 for a two-day stay on Friday and Saturday and will include transportation in a chauffeured driven vehicle for those engaging in a little wine tasting.

Greenport is an easy excursion from the city either by car or by mass transportation. You simply take the Long Island Expressway to the last exit from points west and head to east to Greenport if you decide to drive out. Visitors can ride the Jitney bus directly to Greenport from Manhattan, the last stop on the North Fork line, or take the Long Island Railroad (LIRR) from Penn Station. Simply ride the rails to the end of the line and you will find yourself on the shore of Greenport Harbor. From there you can walk to your hotel or bed and breakfast accommodations and spend the day, the week or the entire summer in this Village, walking with one foot in its seafaring past and one in its very determinedly and oh-so hip and trendy present.

Claudio's Restaurant located at the foot of Main Street is the oldest establishment in the Village founded in 1848 by the Claudio Family. The Claudio's still own and operate the colorful spot known for its distinctive bar and lobster salad sandwiches.






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Guest (Tough Tony) from greenport says::
Greenport is the best place to be and Dave Kapell deserves all the credit for it's turnaround. Go to Claudio's where the action is and the best security staff in the world those guy's make it a safe atmosphere
Sep 1, 2016 6:58 pm

Guest (Guest) from Babylon, NY says::
I visited Greenport over the course of 32 years and consider it to be my home away from home! In fact, it's better than home for me! I wish I could spend my eternity there.
Oct 23, 2010 9:02 am

Guest (Guest) from greenport says::
Well your an idiot sagboi greenport is a very nice place to come, it is the locals that enjoy hanging around mitchells at night to have fun
Sep 17, 2010 11:07 pm

Guest (Guest) from NYC and NoFo says::
Greenport is a great town. I hope it never gets tainted like the Hamptons. I am all for the success of mom and pop stores/restaurants here on NoFo-but never to the extent of the Hamptons. Quaint and unspoiled is perfect up here!
Aug 27, 2010 11:40 pm

Guest (Sagboi) from Sag Harbor says::
Had a business for many years on both forks. There is no excitement on the NF thats why everyone goes to the SF. If you want an over priced dinner from a wanna be chef you can find that in Greenport along with a few Hampton wanna bees and and free gang memebers walking the streets after hours. The north fork is nice quite and tranquil in the summer months but a little over priced for what they have to offer. I vote Hamptons anyday for a chicer night out go to east hampton or sag or even bridge hampton you cant beat it any where, and the prices are worth it.
May 27, 2010 3:53 pm

Guest (new yorker looking for peace) from nyc says::
uugghh ... please stay away from north fork... greenport has always been the best kept secret.. no need to tarnish! please go to the hamptons-- it's more fun!!
Jun 15, 2009 8:36 pm

Guest (carl b) from sag harbor says::
Good story-
Jun 3, 2009 11:45 pm

Guest (millimil) from mattituck says::
I hope Greenport remains trendy, laid back and bohemian... Fun not pretentious...
May 23, 2009 9:26 pm

Guest (Porter) from Greenport says::
Dear South Forker- that "hamptons sludge" as we call it that keeps oozing across making its ways to Sunset Beach on Shelter Island from the Hamptons is the last thing we want on the North Fork. We want to improve our village not destroy it and make it into a dumping ground for NYC crowd.
May 19, 2009 7:53 am

Guest (North Forker) from Southold says::
Won't happen- the NF isn't into the fawning the way that the SF is.
May 15, 2009 7:17 pm

Guest (South Forker) from Water Mill says::
This sounds very hopeful. As in hopefully all the celebrities that the local media fawns over on the South Fork will now start going to Greenport to catch the wave of excitement there.
May 15, 2009 9:49 am

 

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