Our visit to New York with kids was rounded off with time in the countryside and mountains, up near Woodstock in the amazing Catskills region. All 3 sections of this trip could be done in any order you wish to work for you and your flight times.
For now, buckle up and join us on the final segment of one of our favourite holidays to date! Catskills here we come!
- Sleepy Hollow — Scenic Drive, Spooky Stories
- Kaaterskill Falls — Family-Friendly Hike
- Ashokan Reservoir & Woodstock — Nature and Nostalgia
- Conclusion & Tips for Road Tripping New York with Kids
Day 7: Sleepy Hollow — Scenic Drive, Spooky Stories
We finished our family time in New York, picked our rental car up from the same place we’d dropped it off and then headed north. We waved goodbye to the city as you drive north towards Catskills our base for the next 2 nights.
But rather than driving straight there we set our eyes on a stop off point. We couldn’t miss out on stopping at Sleepy Hollow on the way though – it was Halloween after all and we are so pleased we did.
It’s only 40 minutes from Manhattan and a good place to grab lunch in the village, then wander the historic cemetery, a treasure trove of local lore and legend. Older children will love learning about the tales of the Headless Horseman while little ones can enjoy the leafy scenery and riverside views. It’s a perfect blend of history, nature, and a gentle dose of spooky fun – and of course you need a photo with the famous sign!
We easily spent 2 hours here and could have spent longer if we didn’t need to get north to Woodstock for Trick and Treat fun!
You can easily visit Sleepy Hollow on a day trip by train from the city as well. A great idea if you feel you need to escape the hustle and bustle!
For food we can’t recommend Beekman Alehouse enough for pizzas and beers. It’s in the centre of the village and is so popular they queue out the door – we got lucky and waited just 10 minutes for a table and it was worth it.
In the Catskills we stayed in a beautiful cottage just 15 minutes from Woodstock. It came with a sauna, 2 bedrooms, a lounge and kitchen and the kids loved playing in the garden. It’s also a 2 minute walk to a great pub, The Pines, where we ate on our last night and the food and service was great. There is a supermarket just a 5 minute drive away and the Catskills Visitor Centre is a similar distance.
Day 8: Kaaterskill Falls — Family-Friendly Hike
After 4 days in the city we were ready for some countryside. Definitely make Kaaterskill Falls your number 1 hike in this area. It was a 40-45 minute drive from our home, but so worth it. The walk from where we parked was a steady 30 minutes but the terrain was not at all pram friendly and little toddler legs may struggle.
We first headed for the viewing platform which leads you through lush forests to the best view of this stunning waterfall. There’s some brass rubbings along the trail to keep your eyes out for too.
From the platform you will see people down below at the bottom of the falls – we would definitely recommend doing this as the view is amazing. It is clearly signposted but there are a lot of steps – over 600 hundred each way according to Lissie and it is steep in places.
I don’t think I would personally do this with a child in a carrier so perhaps best for kids ages 6 and up. There’s no facilities at all so bring plenty of water, and be sure to wear sturdy shoes. The falls themselves are truly breath-taking and provide an unforgettable backdrop, especially with the magical fall colours.
Day 9: Ashokan Reservoir & Woodstock — Nature and Nostalgia
On our final day in New York (we had a night flight out of JFK) we headed for the tranquil Ashokan Reservoir, ideal for a peaceful stroll and wildlife spotting. We walked over the Ashokhan damn which offered amazing views of the water, the Catskills mountains and the autumn colours.
We saw an eagle and 2 dear in the woods and since there is no traffic the kids could run freely and safely. It took us around 45 minutes for a leisurely walk across the damn and onto the island, and then the same coming back.
Before heading back to the airport, we would really recommend that you pop into Woodstock, a bohemian town famed for its music heritage and laid-back vibe. Wander the quirky shops, grab a snack in a local café, and soak up the relaxed atmosphere. We also had an amazing lunch at Yum Yum Noodles and could have easily spent another 2-3 hours exploring the town more. Again, if you have more time, there is plenty in Catskills to keep you busy for 4-5 days.
The drive from Woodstock to JFK was easy for the first 2 hours, until we hit Manhattan traffic so allow a good 3.5 hours before you need to be at the airport.
Conclusion & Tips for Road Tripping New York with Kids
Travelling New York with kids is a fabulous way to bond as a family and introduce your kids to a dazzling mix of city excitement, natural wonders, and local culture. New York State really impressed us and we were so happy with the route we chose and activities we did – getting out of Manhattan and seeing more of New York State was easily the best decision – so often overlooked as Manhattan takes all the glory!
We hope this ultimate New York family road trip itinerary has inspired you to start planning your own New York roadtrip adventure with the kids.
