The Coastal Village of Greenport is a Family Friendly Gem

Claudio’s dock

Greenport is a quaint village with many surprises to entertain every member of the family.  It’s near the end of the North Fork on Gardiner’s Bay which leads to Block Island Sound and then to the Atlantic Ocean.  You can arrive by car, boat, train, or bus.  The shops are filled with food, antiques, gifts, decor, sweets and more.  One of our favorite restaurants is Claudio’s, right on the docks.

Claudio’s is a National Historic Building circa 1845 complete with a Victorian bar, swinging saloon door, amazing historic photos and (our favorite) the Prohibition trap door. (If you catch the bartender at a reasonable lull in his duties ask him about the trap door.)  The colorful past of this restaurant makes it memorable and entertaining.  Claudio’s is known for its fresh seafood in the New England coastal tradition, but there’s something for everyone on the menu as it is American cuisine.  As with most East end eateries, expect quality fresh ingredients and local wines with a genuine warmth from the staff.


There are many delicious options in Greenport for food and many options to burn off the calories.  Greenport is filled with activities throughout the year- festivals, carnivals, live music, Tall Ships, and Mitchell Park’s endless array of events.

Mitchell Park is a four acre green park on the waterfront of Gardiner’s Bay within the village.  It hosts an observation deck, boardwalk, marina, cultural , artistic, and educational events.  Visit:

Carousel "jousting"

In Mitchell Park you will find an exquisite Carousel that was built 100 years ago in North Tonawanda, NY at the Herschell Carrousel Factory .  If you’re a carousel enthusiast like our family, you’ll be interested to know that 22 of the 36 horses are hand-carved wood.

Gold Ring wins a free ride!

This carousel is open year round, but only on the weekends in the off-season.  The carousel is protected from the elements in a stunning house with giant glass doors that open or close depending on the season and weather.  Rides are $2 each.  Riders who sit on the outside row of horses can “joust” for the golden ring and win a free ride!  Their full schedule can be found online.  Visit:

Waterfront towns are still open for business in the winter and Greenport is no exception.  Mitchell Park hosts an outdoor Ice Rink for skating.  Their rink is seasonal and weather permitting.   Rentals are available.  It’s a small rink, but loads of fun, especially with the beautiful ambience.  Prices to skate are reasonable: Adults $5 ($10 weekend, holidays), Under 18 & Seniors $3 ($7 weekend, holidays).  For full information Visit:

There’s so much to experience in this historic town!  Here are a few more suggestions: 1840 Schoolhouse Museum, East End Seaport Museum, Fireboat Firefighter, and Greenport Jail and Police Museum.


Beautiful Tall Ship(At the same link you can also find information on Greenport’s awesome Skate Park.)

Just one of the many festivals…The annual Maritime Festival happens in September.  It starts on Friday night with the Land and Sea Gala cocktail party.  It continues on Saturday morning with a parade through downtown that kicks off the festival, followed by grand displays of classic wooden boats, kayak races, and demonstrations of water sports, wood carving and model ship building.  You’ll also enjoy music, delicious food, artisan vendors, children’s activities, fresh oysters, craft beers and local wines.

img_0040.jpgCheck out this one too…Greenport Holiday Festival (runs 11/25-1/1).  Visit:

If you’re looking for more adventure…

The Shelter Island Ferry is located right next to Mitchell Park.  These small ferries travel year round and are a short ride across a narrow section of the bay to Shelter Island.  There are no reservations – traffic is boarded on a first come first serve basis. Vehicles and bicycles pay on board, they accept cash and checks only.  Passengers $2, Vehicles $11 ($16 round trip),  every 10-20 min.  Visit:

Shelter Island across the Bay

From Shelter Island you can hop across the bay again on the other side to North Haven which is a quick 4 mile drive to Sag Harbor on the South Fork This ferry also travels year round and is a short ride across a narrow section of the bay.  Passengers $1, Vehicles $14 ($17 round trip),  every 15 min.  Visit:


For more transportation information:


Hampton Jitney:

Family Adventure Rating ♥♥♥♥♥

Cost- Outside of transportation costs, it’s up to you on how much you spend. We’ve visited just to window shop, ride the carousel and get some ice cream. We’ve also passed through to eat at a local business, have ice cream, and ride the carousel. And, we’ve also come to buy those items we loved when we were window shopping, then get ice cream and ride the carousel. If you have the extra money to splurge, eat at Claudio’s. (Don’t forget to ask the bartender about the secret trap door and check out the cool pictures on the walls.)

Parking & Transportation– There is plenty of parking, but on a busy day you may have to drive around to find a spot. There are town lots that are free and plenty of free residential street parking. There is a train station for the LIRR that brings you right into town next to the ferry terminal (and Mitchell Park). You won’t need a taxi from there, but there are ones available.

Mitchell Park under snow

Location– Greenport is a quaint waterfront town with fun history. It’s remote location at the end of the North Fork keeps it from changing too much. It does cater to a lot of traffic from avid boaters, ferry passengers going and coming from Connecticut and Shelter Island, locals, and North Fork adventurers. This traffic keeps the town open even in the winter months.

Day Trip or Overnight– You could certainly stay at a Bed and Breakfast and truly enjoy the area. But if you’re pressed for time and/or money, this is an easy day trip from anywhere on Long Island or even NYC.


Experience– If you love a good fishing village or even some old warm charm, then this is a perfect town for you.  Yes, it has some “trendier” stores and restaurants popping up, but they don’t change the overall feel of the town.

Combination– There’s a ton of adventures in and surrounding Greenport. Antique Carousel, prohibition passageways, old jailhouse, old schoolhouse, quick ferry to Shelter Island, Orient Point State Park!, lavendar farm, farmstands, goat farm, etc.



Published by newyorkfamilyadventures

Momager, New Yorker, Travel Blogger, Actress, Martial Artist, Amateur Photographer, Writer, Conservationist

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