From Planning to Ponies: Chincoteague Island, Virginia (Part 1)

Part 1: I Booked It?

Since we got back from Chincoteague, Virginia, in early August, I have been thinking about how I would write about it. How could I capture our time in that enchanting place?

Words, even the most precise and polished, can’t contain the experience I had with my family in Chincoteague. But travel is about the impression one comes away with, ultimately. And from the start, our journey to Chincoteague was full of feeling.

First, I need to backtrack. In a previous post, “Horse Girls,” I discussed my mother’s love for the horse book Misty of Chincoteague as a little girl, which she passed on to me, and I read to my girls. When I was very young, we even visited Virginia during the famous Pony Penning Week, an annual event where the wild ponies on the adjacent island of Assateague are swum across a channel to Chincoteague. I always dreamed of visiting Chincoteague someday with my daughters.

The problem is, Chincoteague is a small island with only a limited number of places to stay. Every year I’d search for a room during the pony events in the last week of July, and every year I’d find the same results: “Sold Out.” Supposedly, visitors to Chincoteague will even secure their reservations at check out for the next year! It felt unlikely that we’d ever make it there unless we stayed somewhere else and commuted, which would likely be chaotic considering the crowds of tourists who descend upon the island and the fact that only one road connects it to the mainland.

Plus, it just so happened that 2025 was the 100^th Anniversary of the Pony Swim. The turnout was expected to be record-breaking.

I am nothing if not determined, however. One of my favorite pastimes is to plan potential trips, similar to the way some people window shop. In mid-December, 2024, I was browsing on the app for our preferred hotel chain, and I typed in “Chincoteague.” This time, besides the “Sold Out” establishments I normally encountered, a new location in Chincoteague advertised “Coming Soon.” Immediately, I called the phone number listed. A front desk agent answered and informed me that their existing hotel was changing brands. Due to this, yes, a few rooms were still available for Pony Penning Week.

Without batting an eye, I booked it.

Then I sprung the news on my husband: “Hey, dear—guess what! We’re going to Virginia next summer!”

Thankfully, he was supportive.

The next issue I ran into was that most guides to Chincoteague recommend taking a boat tour in order to have a good view of the Pony Swim. The only other option is to watch it in shin-deep muck along the marsh edge shoulder-to-shoulder with thousands of others, fighting for a glimpse of the real thing while it’s broadcast on a big screen. The boats are expensive, naturally, as this is the island’s biggest tourist draw of the year.

But Anthony hates crowds, so he encouraged me that a boat with a capable captain would be worth it for this once-in-a-lifetime opportunity.

I called probably a dozen boat tour companies, if not more. Either the situation wasn’t ideal (“The boats are all sold out, but we have a couple canoes left. Just be careful of choppy waves; your kids should be fine”—when we’ve never canoed before) or I’d be quickly disappointed (“Sorry, we don’t have any more spots open, but you can be #17 on the waiting list”).

Eventually, scrolling website after website, I stumbled upon a captain’s phone number which seemed like a personal line. His small business did have a website but it hadn’t been updated for years. When I called, the friendly lady on the other end covered the phone with her hand and yelled, “Hey, I’ve got a family of four asking about Pony Swim—think we can do another boat?”

“Yeah,” a man’s voice said gruffly in the distance. “I guess.”

Crossing my fingers, I read her my credit card details. I requested a confirmation and received one via email that was hand-typed on some sort of note application that I could only open on my laptop, not on my phone.

Please let us not get ripped off!

A month or so later, the hotel called to say that since they converted to the other brand, I needed to pre-pay to keep the reservation. Again, I couldn’t do the transaction online, I had to read my credit card and wait for a dubious receipt via email.

As the months passed, I wondered, Will we get there and have nowhere to stay? Will there actually be a boat waiting for us? Or did I just throw money into the sea?

The kids were also somewhat incredulous of my feat. My oldest daughter would shake her head and laugh, asking, “How is it possible that after all these years, you were able to get a room for the hundredth anniversary?”

We’ll see, I would think to myself. I’ll believe it when it happens. Because it felt so out of reach for so long, a part of me didn’t really believe it was going to come true.

To be continued . . .