A Winter Boat Ride to Spy Chincoteague Ponies

Little did I know when I first traveled to Chincoteague, the island whence my favorite book Misty of Chincoteague sprouted, and the spot where I uncovered part of  Marguerite Henry’s backstory, it would beckon me to its shores on repeat. You could say I’m a Chincoteague Island boomerang.

The first week of 2026 I returned to the land of Misty, and I tried something new (which I highly recommend to you): pony watching from a boat. Before we sail into that story, I’ll give you a taste of Chincoteague in July during the famous pony swim week. January v. July is certainly a study in contrasts!

First Pony Swim Week Impressions

Rolling down the causeway to Chincoteague in July 2022, I remember tilting my sunglasses to see if the color intensity of the green salt-marsh grasses was real (very real). Swooping seagulls flew ahead of my path, heralding my adventure of a lifetime. Dozens of quaint billboards in a row greeted me with suggestions for island dining, boating, shopping and houses of worship. 

For years I had dreamed of seeing the real wild Chincoteague Ponies I had read about in Marguerite Henry books when I was a kid. Now as an adult, I wanted to find out everything I could about them and about the real Misty pony and her author friend Marguerite.

I settled into my hotel room, and set my alarm for 4 a.m. in order to glimpse the northern herd beach walk.

The Atlantic sunrise, a tie-dyed sky of oranges and blues, served as a backdrop for the Monday morning pony drive. Cowboys ushered scores of bays, chestnuts and pintos along the shore to a holding corral.

Tuesday, I stood among dozens of other pony watchers drinking in the view as foals, stallions and mares milled about their holding corral. A liver chestnut stallion mounted a mare right in front of my eyes! Seconds later, when the deed was done, a lanky foal reached out its muzzle and sniffed the stud. I assumed the stallion would wheel around and squeal and put the curious toddler in his or her place. Nothing happened! 

This pony behavior was fascinating to watch—like a PBS wildlife program, but in real life.

And then Wednesday dawned—Pony Swim Day!

Atop the water in a tomato-red kayak, I witnessed a pony pageant of my dreams—the wild swim scene—an iconic plot point brought to life by Marguerite Henry’s beautiful words and the vivid brushstrokes from illustrator Wesley Dennis. 

I had more Pony Penning Week adventures, which you can learn more about in my memoir Marguerite, Misty and Me—the book that I set off to research during that inaugural trip. But for now I want to share a novel experience with you—a boat trip to Assateague to see the wild herds in their habitat.

New Year, New Fun: Pony Watching from a Boat

Rolling into Chincoteague along the causeway this time, the marsh grasses had swapped out their summer green brilliance for a warm, caramel tone. The birds and billboards greeted me again. I noticed one thing different about the quaint downtown: sparkly seashore creatures adorned the light poles downtown. “This looks like a Hallmark movie set,” I told my road trip buddy Rebekah. Since I was at driving, I pestered her to take pictures of the festive decorations.

As I drove, I excitedly urged Rebekah to get pictures of the various Christmas decorations. Blue crabs, lobsters, praying hands, shrimp, Misty’s head,

I had seen the wild ponies swim several times, but had never taken a boat to see the ponies hanging out in their marshland habitat. That all changed the first week of 2026, when a small group of fellow pony watchers and I hired Daisy’s Island Cruises for an afternoon boat ride. 

The water was placid and shimmery. The sun shone brilliantly even though the temperate was in the low 40s. A local had warned me that on the water, it feels 20 degrees colder. Taking that admonition seriously, I wore three layers of pants: yoga pants, jeans and sweatpants. And I borrowed a turquoise scarf with stallions striding along the front. My fleece-lined blanket, which I keep in the back of my Jeep in case of a road emergency, joined us for the ride.

During the first half of the trip, the ponies eluded us. My friend Amanda teased that I was keeping them away. Apparently every other time she has been on pony spotting adventures, the bands show themselves. 

While there were no ponies to be found, unique birds abounded! Fun fact: Chincoteague Island is indeed a destination for birdwatchers.

The highlight for me was two bald eagles soaring overhead. Their unmistakable white plumage set them apart from other birds of prey. 

After the first sighting, we encountered another bald eagle resting upon some trees on the water (maybe a duck blind?) but by the time I positioned my camera, he or she had flown away. Thankfully, my boating comrade Amanda was quick with the snap and captured the above beauty mid-flight. 

The orange-beaked oyster catchers were hilarious, hyper focusing on tiny tide pools in search of lunch. They looked so serious—until they moved into new hopeful positions by hopping along on one leg in a silly gait. 

The formerly chartreuse grasses from July presented as a mellow tawny tone.

We finally found ponies! The first band was so far away I would not have even noticed them. However, our two boat captains possessed mad pony spotting skills, alerting us to the tiny moving dots on the marsh waaaay off in the distance. They reminded me of the safari guides I met eons ago in Botswana—their eyes noticed leopards and lions I would have never seen. Bundled up in the boat, I wished I had my binoculars.

As the ride continued, we finally got much closer to the ponies. We found a palomino mare grazing a distance away from the rest of her band. She was very color-coordinated with her surroundings and completely ignored us, ambling back and forth in search of the best mouthfuls. Look at those dapples!

A rotund buckskin mare who wouldn’t turn to face us showed us the promise of spring foaling season. Now I think it would be perfect to head to Chincoteague in April or May. Not only will it be warmer, but then I could see foals! Captain Sydney shared there’s a bit of a friendly competition with the boat captains—tracking each new foal. 

One of the most remarkable things about the captains and my three pony-spotting companions is that they can identify each pony by name—even the solid bays. After we saw maybe a few dozen ponies, all in small bands scattered across Assateague, we headed for the marina. Sunset readied itself for showtime, but not before we snapped a cute group shot to commemorate the fun afternoon with ponies—and oystercatchers.

Thanks for reading about my three-hour tour with Chincoteague Ponies! And if you love horse books, grab a copy of my free guide to help you plan your next feel-good read.

P.S. If you’re heading to Pony Club Convention in Lincolnshire, IL, January 29-February 1, come say hi to Rebekah and me. We’ll have a booth promoting Chincoteague Ponies, and I’ll be selling all my horse books, including Marguerite, Misty and Me. I’d love to meet you and sign a copy. Sunday, February 1 we are presenting a talk “From Wild to Wonderful: Discover the Chincoteague Pony.” See you there?

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