Iconic New York with kids: The Most Epic Family Road Trip

new york beach

Part 1: Long Island. The starting point for your New York with Kids Road Trip Adventure.

If you’re dreaming of a family holiday packed with excitement, discovery, and a dash of adventure, look no further. New York blew us away during our autumn October half term break – we genuinely think October may be the best time to visit New York with kids. Halloween for starters is immense!

halloween in new york

The Background – why a New York road trip with kids

Roadtrips have become a family-favourite holiday format for us. Some of our favourite time and holidays together have been our roadtrips through Taiwan, Guatemala and Denmark.

New York came about after finding surprise flights for £200 per person retrun from London which we couldn’t believe. These cheap flights were only for this 10 days period, but we never struggle to fill out time and I am so pleased we could add 6 days to a city break and explore more of what New York has to offer – it’s up there as one of our best family holidays.

This New York family road trip itinerary was brilliant especially for travelling with kids! From exploring local breweries and charming seaside villages to marvelling at Manhattan’s iconic toy stores and hiking to breathtaking waterfalls, you’ll find something to delight every member of the family – we certainly did.

new york with kids

It’s worth noting that we landed late into JFK, so we stayed near the airport on our first night and set off around 10am the next morning – direction Long Island. This route was also dictated in that we were seeing friends in Manhattan in the middle part of our stay, but you could do Long Island, Manhattan (Part 2) and Catskills (Part 3) in any order really.

Our rental cars cost £116 for 3 days each time, so £232 in total for 6 days hire. We collected our first rental from JFK and dropped it in Manhattan, and then collected another from Manhattan and dropped it at JFK before flying out. This did save us money on taxis to and from Manhattan, fuel was affordable but you will hit some of the tolls during your time.

Driving in another country really doesn’t phase us and the US is so easy as the roads are empty and all cars are automatic. Even driving in and out of Manhattan was ok.

So buckle up and join us as we hit the road on the ultimate 9 day New York family adventure!

Day 1: Riverhead & Jamesport – Family-Friendly Breweries and Local Charm

Kicking off your New York family road trip, head from JFK to Riverhead on Long Island’s North Fork. It’s around a 90 minute drive and this area is famous for its relaxed, family-friendly vibes. We stopped off at Riverhead for a stroll and to pick up some lunch but what we found was a beautiful town with a river walk, a gorgeous book store, the best bagels – and we stumbled across a guy offering free crochet lessons on a picnic bench by the river. That sums up the vibe of this place. He spent an hour with Alicia and gifted us all crochet hearts.

There is also an aquarium and miniature railway here if you do want to spend longer in Riverhead. It could also be a good base to explore both the North and South Fork of Long Island.

At the end of Long Island there are also many local breweries offer gorgeous outdoor spaces, tasty non-alcoholic options, and even play areas for kids. Jamesport is just a short drive away, boasting more breweries and cideries, plus scenic countryside perfect for a picnic or a runabout. Parents can sample local craft beers while little ones enjoy fresh-pressed apple juice. There was live music, pumpkin ale and beanbag games for the kids. It helped the sun was shining but we would totally recommend a stop off at Jamesport Brewery on the way to Greenport.

Along this north fork road to Greenport, we also passed a lot of maize mazes, pumpkins farms, Halloween fun and wineries. There would be plenty to do if you wanted to spend longer in this area.

We stayed in Greenport for the 2 nights we were on Long Island at a brilliant holiday cottage and RV park; North Fork Cottages and RV Park. There was a pool (seasonal), a play area and Halloween fun for us, and there was a fire pit with logs and lighters provided.

The cabins are very much luxury and it’s only a 5 minute drive to the centre of Greenport with its carousel, live music bars and quaint streets to roam. There’s not loads to do in Greenport itself, but its got lovely restaurants, a supermarket and a small beach area so an evening here is a lot of fun.

Day 2: Greenport to Shelter Island, A Car Ferry Adventure & Coastal Fun

On the second day, to Greenport and board the car ferry to Shelter Island. Now this isn’t cheap, at $35 same-day return, but children will love the novelty of boarding a car ferry to Shelter Island, driving through an island population and then boarding another ferry to hit the south fork of Long Island (another $30). Not taking the ferry would have been 1hr 15 mins drive. Once ashore you are pretty much in The (infamous) Hamptons. Enjoy spotting the mansions as you drive along, and hit some of the amazing beaches.

We can’t recommend both Indian Wells Beach and Sagg Beach enough. Sagg beach was full of treasures for the kids to find and the light in October was magical. There was a car park which was free at this time of year but toilets were closed.

Both beaches were empty and we spotted dolphins from the coast. There’s not many facilities at either so take food and drinks if you plan to be there a while. I can imagine it’s busier in summer, but on a blue-sky autumn day we had so much fun running, paddling and exploring the dunes.

From here you aren’t far from Jackson Pollock’s grave and home museum if you are into art.

Don’t forget to leave time to stop in Sag Harbour before returning on the car ferry home. It’s a picturesque town with ice cream shops, quirky boutiques, and a lovely marina for a family stroll.

Read Part 2 of our New York road trip here – next stop Manhattan! And exploring New York City for 4 days with the kids in tow.