Boston Family Road Trip Destination: North Fork, Long Island

If you ask most families in Boston about suggestions for road trips, you’ll get a lot of the same answers – the Cape, Maine, Vermont, and New Hampshire. What you won’t hear as often is Long Island. Yes, THAT Long Island. Tucked away on the North Fork of Long Island is an absolutely delightful family travel destination.

I was recently invited to visit the North Fork of Long Island to get the experience of all the family-friendly offerings that the area has to offer. Take a look at what I’ve found and then book your trip. It was so close, so much fun, and so DIFFERENT than most of the fun standbys.

CSF_EditedOur trip started on The Cross Sound Ferry. The Ferry departs from New London, CT and makes the trip over to Orient Point, NY in Long Island.

It took about 1.5 hours from my home in Metrowest Boston. Such an easy drive too! At the Ferry terminal, you can either park your car or actually take your car on board with you. For families on their first trip, I’d suggest taking the car. It gives you more options and an easy way to explore all of the activities. Check out the Cross Sound Ferry web site for information on schedules and fees.

There are so many great opportunities for fun activities for families traveling to this area of Long Island. One of them is Harbes Family Farm in Mattituck, NY. You could honestly spend the better part of a day here. There are activities for the whole family from good food to fun activities to animals and even wine tasting. Here’s a few scenes from the farm.


Our next stop was Bedell Cellars. Wineries for the family, you ask! This particular winery is a great destination for a family picnic. If you have a few adults in your party, you can even take turns visiting the tasting room.

Bedell Cellars’ merlot was one of the wines poured at the 2008 Presidential Inaguration.

Here are some great shots of the vitner and the vines at the vineyard.



Where to stay?

A great option for families is the Harborfront Inn in Greenport, NY.

I had the opportunity to spend the night in the Shorecrest Bed and Breakfast and it was truly delightful. If you take this trip as a couple trip, this B&B is a perfect place to call home. All is not lost for the family adventure though. The wonderful innkeeper, Marilyn, manages a number of North Fork vacation homes adjacent to the B&B. These are just right for a family visit.

Take a look at the inn, the beach and the wonderful breakfast that Shorecrest serves.

shorecrest 680

There are so many ways to have a great trip to the North Fork of Long Island. The combinations are unlimited. Check out and for other ideas and event listings.