How to Spend a Weekend in Long Island’s Wine Country

There are more than 30 vineyards along the North Fork, not to mention many multi-generational family farms and beautiful rural scenery. This 30-mile long peninsula is a wonderful spot for your next vacation. Though it is only 90 miles away from New York City, this peaceful peninsula feels like its worlds away from the hustle and bustle of daily life.

If you’re planning your next trip to Long Island wine country, you’re probably starting to think about building an itinerary for the weekend.

How should you spend a weekend in wine country?

Let’s take a look at some of the best things to do in Long Island wine country so this can be a weekend to remember.

Visit Farm Stands and Farmers Markets

As one of the last remaining vestiges of country living on Long Island, it’s worth checking out the local farm stands and farmers’ markets on the North Fork. You can find miles and miles of farm stands along the long strip of land that leads to Orient Point. There are also wonderful opportunities like taking hayrides in autumn or pick-your-own berries spots in the summer.

Relax at the Beach

If you’re looking for things to do in Long Island wine country, don’t forget one of the best things you can do on vacation: relaxing! It’s easy for a vacation to end up feeling like a chore in itself, rushing from one item on your itinerary to the next. In between Long Island wineries, be sure to soak up the sun and relax on one of the beautiful beaches that line the North Fork.

Take Some Wine Tours

A great way to explore the many Long Island wineries is to take a wine tour. Rather than having to drive yourself between wineries, you can be chauffeured between the best vineyards on the North Fork.

Go Golfing

There are a number of primly landscaped golf courses to enjoy when you are exploring wine country. You can find everything from beginner-level courses to professional-level courses as well as both 9-hole and 18-hole layouts.

Take a Guided, Luxury Bicycle Tour

One of the best ways to explore Long Island wine country is on a beautiful bicycle excursion. East End Bike Tours offers a gentle 13.5 mile guided, luxury bike tour that takes you through the North Fork Vineyards. Along the way, you’ll be able to enjoy picturesque vineyards, scenic views of the Peconic Bay, historic landmarks, and tree-lined streets.

Every detail of the trip is taken care of for you from the moment you arrive at your bike tour. Tour guides will learn about your culinary needs, cultural interests, and any particular requests you have to make sure that the experience is absolutely perfect and one-of-a-kind.

You can even book a brewery and vineyard bicycle tour, so you can have a lovely and relaxing time exploring the outstanding breweries and vineyards of the area.

Have Some Family Fun

If you’re worried about whether or not your kids will be bored in wine country, don’t fret! There is a lot of fun to be had for children along the North Folk. With water parks, carousels, bike rental spots, and an aquarium, there is plenty to keep the whole family happy.

Take a Trip Down the Peconic River

One of the best ways to explore the local land and see local wildlife is to take an adventure down the Peconic River. You can rent canoes, kayaks, and paddleboards and have an exciting afternoon floating downstream.

Visit Local Museums

If someone in your family is a history buff, you might want to check out some of the local museums.

The Railroad Museum of Long Island is a wonderful place for train-lovers and the curious alike. Located in a former freight house, this museum has a number of rare historic treasures.

The East End Seaport Museum has other objects of local and historical significance. It is situated in a building that was originally part of the Long Island Rail Road.

The Southold Indian Museum is a great way to connect with the history of this region of Long Island. You can see spearheads, fishing tools, arrowheads, soapstone bowls, and so much more here. With the largest collection of Algonquin ceramic pottery, this is a way to get a sense of this area’s ancient past.

Take a Fishing Charter

If you’re taking a Long Island wine country vacation, another fun thing for the family is to take a fishing charter. You can set up a half-day, all-day, or nighttime trip with a knowledgeable captain. That way you can be sure to come home with the biggest catch and have a great time along the way.

Enjoy the Local Dining Scene

There are tons of North Fork restaurants for you to enjoy when you’re on vacation, no matter whether you’re looking for a casual or a fine dining experience. That being said, you’re definitely going to want to check out one of the seafood shacks when you’re here!

What Will You Do When You Come to Wine Country?

If you love to multi-task, then taking one of our bike tours might be the perfect activity for you and your family. All in one adventure, you’ll be able to sight-see, sample, indulge, shop, exercise, and take photographs. We offer a wide range of tours as well as bike rentals so that you can have exactly the experience you’re looking for.

Are you planning your wine country trip? If so, check out our bike tour options here!


Article courtesy of Jason Levine from