NYC: Train Trip with Sleepy Hollow and Walkway Over Hudson

Our tour begins in the center of Midtown. From Grand Central we will take Metro North up to Tarrytown and Sleepy Hollow. There we will explore this historic area and you will learn about its most famo

Our tour begins in the center of Midtown. From Grand Central we will take Metro North up to Tarrytown and Sleepy Hollow. There we will explore this historic area and you will learn about its most famous resident: Washington Irving. Trace the path of Ichabod Crane and the Headless Horseman. We will visit the Old Dutch Burial Ground and Church. After a brief coffee and pastry break, we will take a majestic train ride up to Poughkeepsie where you will be able to experience the new jewel of the river, the Walkway Over the Hudson. We will take a brief elevator ride to the top where you will get incredible views. From there, we will take the train back to the Hudson Highlands where we will visit the charming village of Cold Spring. You will experience views of West Point and the sheer cliffs of Storm King. The tour ends here, but your day need not end- spend the day here or go onto another town!

From: $0.00

Location: New York City

What's Included

Community Discussion

Q&A

Q: Is there an age limit for this train trip experience? Can kids join?

A: There’s no specific age limit for the trip! Kids are definitely welcome, and many families take this tour together. The walk at the Walkway Over the Hudson is pretty easy, so it’s great for kids. Just keep in mind there are some historical sites where kids might need a bit of guidance.

Q: What if the weather is bad on the day we booked?

A: If weather conditions are severe, you can usually reschedule the trip. Bobby’s City Tours is pretty good about that. Just reach out to them as soon as you can. The Walkway is outside, so if it’s pouring, it’s best to wait for a nicer day!

Q: How much walking is involved, and what should we wear?

A: There’s a fair amount of walking, especially in Tarrytown and on the Walkway Over the Hudson. I’d suggest wearing comfortable shoes, maybe some light layers depending on the weather. It’s not overly strenuous, so you’ll be fine if you’re moderately active.

Discussions

Just booked the NYC train trip with Sleepy Hollow - anyone else done it?

I just booked the train trip with Sleepy Hollow and the Walkway Over the Hudson! I’m super excited because I love Washington Irving's stories. I’ve never been to Tarrytown or Poughkeepsie, so I can’t wait to explore. Anyone have tips on what to check out while we're there? How's the coffee at the stop?

Thinking of gifting the NYC train trip - any advice?

I’m considering getting this NYC train trip experience for my parents' anniversary. They love history and scenic views. Do you think they’d enjoy it? Is the trip easy to manage, or is it more complicated than it seems?