From Planning to Ponies: Chincoteague Island, Virginia (Part 2)

This post is part of a series about our summer 2025 road trip. Read about Ocean City, MD, here. Part 1 of our Chincoteague, VA, trip is here.

Dear girls,

Three things have happened which made me decide to write about our trip to Chincoteague as a letter to you. One, is that I am reading a book where the main character writes a letter to his son to read when the son is grown. Secondly, I am teaching a memoir class where we discussed the question, Who are our memories for? And I realized, all my memories are for you.

Then recently, I came across a photo which cleared something up for me. You know the photo my mother gave me, with little six-year-old me standing with a Chincoteague pony in front of a red barn? A similar photo (without me) appeared on social media that named the pony as Stormy, Misty’s foal. Remember we read that book together? Years ago, when I read that pony’s story to you, I didn’t know I had ever met Stormy when I was young.

You see, when we are children, we often don’t know what’s happening as it happens. We know what we are doing, but a greater significance may be yet out of our reach. If we have grownups in our lives who shared those occurrences with us, they may provide insight at a later point, if we are fortunate.

That is what I hope to do with this letter.

So this year we went to Chincoteague, Virginia, as I had been dreaming we would do all your lives. While I planned it, I was apprehensive that it would actually take place, that we’d actually make it there and witness the 100^th anniversary of the legendary Pony Swim. But we made it to Chincoteague on July 28^th, 2025. I won’t go into all the details of our trip to that special place (because surely I will also make a photo album), but I will tell you about the day of the Pony Swim.

We had been instructed to be at the Curtis Merritt Harbor for our private boat trip at 4:00 in the morning of July 30. You both did a great job going to bed early in anticipation of the big day. Even at that point, you would say to me, “I can’t believe of all the years, you were able to take us to Chincoteague for the hundredth anniversary.” It made me proud that you were saying that, like I had some sort of power within me to make things happen.

So we got up at 2:45 a.m. or so, groggily put on our bathing suits and shorts and water shoes that we were advised to wear, and got in the car to wind our way around the island in the pitch dark. The first sign that something exciting was happening were the shadows of people moving along the sides of the road, up before dawn just as we were, for the biggest event of the year. Chairs lined the ditches. We got to the harbor and dad dropped us off to find parking, because it was already so crowded with people. Again, in total darkness, except for the big sky of stars above us.

Because I am a very basic astronomy fan, I already knew that this night of all nights a double meteor shower was to take place! I wished for clear skies, but thought again, perhaps that would be too good to be true. Yet clear they were.

Dad met up with us. It was a little bit chaotic with people milling around in the dark trying to find their boat tours, but we checked in with the boat company and were assigned a boat captain who was also taking his mother and two daughters out with us for the pony swim. I thought how nice it was to be able to meet local folks and share that experience with them. The captain’s name was Derrick, and he was also a member of the Coast Guard, so I figured we’d be plenty safe. He had both of you put on life jackets (even though you didn’t want to).

After a while we were ready to go out into the open water. Derrick’s boat, which had no cover, steered out of the harbor in the wake of some fellow tour boats in front of us. The four of us sat in the front, and once in a while Derrick’s two daughters would join us. I told them about the meteor shower, of which they were unaware. The only unnatural light was from the boat leading the charge. We followed that light even though we couldn’t see anything around us, just some house lights in the far distance.

I stared up as we sped through choppy waters. I had never been on a boat at night! But your dad has, with Grandpa on fishing trips. The Milky Way above us sparkled. Then sure enough, I don’t remember who, someone yelled, “There’s one!” A streak of light cascaded across the sky, and then vanished. Some of us missed the first one. But then—“There!—and this time, each of us saw it. Our whole family and a family of strangers, sharing a moment which felt pretty close to a miracle. We saw several more shooting stars, and I marveled at how they seem suspended in time for just a second before disappearing.

I will never forget this, I vowed to myself. Thank you, Universe.

Our boat reached the tiny sand dune where we’d watched the ponies swim from Assateague Island to the shore of Chincoteague. They’d come right past us, we were promised. Once we docked in a row with the other boats, someone put on country music and the larger boats lit up their grills to feed us breakfast. One boat had a griddle that they flipped bacon on, the smell wafting over to us. One boat brewed coffee and passed it around to the rest. “You want some waters?” Derrick asked us, standing up while we sat. We nodded. Another boat tossed him bottles from a cooler, which he handed to us, our boat rocking ever so gently as he reached to grab them. It was a pre-dawn boat party, and I was here for it.

Eventually we got our bacon, egg, and cheese breakfast sandwiches. They were so massive you two couldn’t finish yours. I admit, I was a little too tired and excited to swallow it down, but I did, because I knew it’d be many hours before we’d be back on land to have our next meal. Then Derrick encouraged us to jump out of the boat and explore the sand dune. By this time, the sun was just starting to peek up over the horizon, painting the sky the prettiest pastels. He approved of our footwear, claiming that many a tourist ignored the boat company’s advice and lost a flipflop in the thick muck, or worse—got cut on the oyster shells that knifed up everywhere in clumps. That scared you, and so you were cautious.

On the sand dune, people gathered, already taking their positions to watch the pony swim. We walked around, took photos, and noted tiny crabs doing their skittery backwards crawl and disappearing into the sandy ground between sharp blades of sea grass. The sunrise turned out to be spectacular show of oranges and pinks bursting across the sky. The morning summer air was the kind of slightly cool which hints at the warmth the day will bring.

Large boats were lining up in the water at this point. Right next to us was a barge two stories’ high with revelers. It belonged to some politician, and the locals noted with an eye roll that it had been parked there for days. The mayor was trolling around in the water, and it was said that Virginia’s governor would be making an appearance as well, dropping in by helicopter. Derrick told us that normally there would be news helicopters circling above, but due to security, this year no flying objects were allowed except officially-approved ones, including a police drone.

Derrick pointed where to stand so that we could nearly touch the ponies as they entered the water. The pattern of the swim had shifted this year—again, due to security—but he was still right, and we had the best view. The problem was, we were standing in ankle-deep murky water for a couple hours to get it! However, you guys took it like champs, barely complaining about having to stand there for so long. There was very little, “My back hurts! How much longer?” I was impressed. The worst part was, there was no bathroom. I mean, there were options, but you chose not to use any of them, and so that became an issue, but that’s all I’ll write about that!

At one point a radio DJ came around with a microphone and interviewed people standing near us, including Derrick’s mother. You nudged me to try to get on the radio, but I didn’t. Small things like that kept us occupied during the wait. We listened to people talking around us. Once in a while, the crowd on Chincoteague would rise up in cheers, and we’d wonder what was happening on land. A media boat came by. We thought the mayor came by. The timed ticked away as the sun slowly arced over us.

The Saltwater Cowboys, who lead the Pony Swim, were waiting for low slack tide to bring out the ponies. This is when the tide is at its shallowest, making it safest for the ponies to swim across. It changes every year, so it is a waiting game. Finally, the Saltwater Cowboys, who were on horseback, took their places in front of us. Derrick showed us that the ponies would be herded off Assateague behind us, onto and across the sandbar where we stood, and then into Assateague Channel to swim to Chincoteague Island.

Suddenly, an uproarious commotion alerted us that the swim had begun. The ponies were a blur behind us, galloping closer every second. Then, in a flash, a mass of ponies snorting and whinnying thundered across the sandbar to our right, to be stopped briefly by the Cowboys at the edge of the shore, before being urged into the water by the cracks of whips and the cries of “Ha!” from the Cowboys. (They didn’t whip the ponies, they whipped the water.)

The ponies crossed right in front of you.

If you know your mother, you know I lived this part with tears in my eyes. I don’t know if I was more moved by those magical wild beasts rumbling before us, the sheer electricity of it, or if it was the fact that I was watching you watching it happen.

The ponies, nostrils flaring, bobbed up and down as they swam across the channel, where they were able to rest on the other side. After months and months of planning this trip and hours standing in muddy water, it was over in mere minutes.

The crowd started to disperse. We went back to the boat with Derrick and the gang, relieved to sit down and breathless at what we witnessed.

When we were able to pull the anchor up and motor out, Derrick let us know he’d take us out into the Atlantic to look for dolphins. We didn’t see any that day, but we did catch three ponies grazing on the shore of Assateague that weren’t part of the swim. Being on a boat in the ocean reminded me how vast this earth really is, how deep down it extends. Silvery waves undulating in every direction, and the eight of us so very miniscule in this mighty world.

Then Derrick sailed us around to the other side of Chincoteague Island to observe the ponies march in the parade. One pony tried to escape the guard of the Saltwater Cowboys. We saw a jellyfish swim past the boat.

When the parade was over, Derrick headed back toward the harbor. A Marine Police boat stopped us because they were being extra vigilant that day, so it was good you were wearing your lifejackets. Derrick produced evidence of an overabundance of lifejackets on board, casually dropped in that he was Coast Guard himself, and we were on our way. The first stop was the bathroom in the harbor station. We drove back to the hotel, dirty and worn out.

It wasn’t even noon.

I don’t know why I’m built this way, I hope you never have this weird sense of disbelief, but I can never fully have faith that something is going to happen until it does. And now, it had. My faith had fully emerged, grateful and awestruck.

And we got to share it together—you, your sister, your dad, and me.

You girls loved it, but you loved a lot about the trip. You loved each ice cream place we tried. You loved swimming in the hotel pool. In the ocean. Souvenir shopping, going to the carnival that night, searching for seashells the morning before we left. And I did, too, girls.

I just wanted you to know that, so I wrote it all down.