SONY DSC (Lois Szymanski)

Every year I return home from Pony Penning on Chincoteague Island, totally inspired and in awe of the way things work out. Even though it is an exhausting week, unfolding events renew us, and give us faith that things frequently work out just as they are meant to be. There are so many stories, but there is one in particular that I have to share with you, my faithful readers.

Many of you know that I go to the annual wild pony roundup and swim with the nonprofit group, the Feather Fund. Each year we purchase children foals in memory of our friend, Carollynn Suplee, who — for the eight years she survived cancer — annually purchased a foal for a child or turnback foal to live on the island forever. It was her way of giving back for another year of life. This year, to celebrate our 15th anniversary, the Feather Fund purchased foals for three children. But the story I want to share is about one of the kids Carollynn purchased a foal for in 1999, before she left us and joined the ranks of angels.


The Feather Fund chooses children through an application and essay procedure, but Carollynn chose them on the spot, asking for guidance from above. In 1999, Matt Loveland was trying to win the bid on a pony, but the money he’d saved was not enough. That is when Carollynn stepped in and helped him purchase his Chincoteague Pony, Ace. It was the first step in his dream of someday becoming a saltwater cowboy who would ride in the annual roundup.

As the years passed, Matt outgrew his pony and passed it on to a neighborhood friend, but he continued to dream of riding in the roundup. Every year at Pony Penning, Matt hung out with the cowboys he had come to know. Over the years, he married and had a son, but his dream did not end.

Last year, Matt purchased a beautiful bay American Quarter Horse named Pepper, one he thought was smart and solid enough to take a strenuous roundup week on the island, with mucky marshes, “herds” of mosquitoes, and rough conditions. He started doing cattle penning competitions, riding and dreaming of that day. And then it came — the call asking him if he would like to ride in this year’s roundup.

A crowd in kayaks watch the Chincoteague Island ponies on swim day.
A crowd in kayaks watch the Chincoteague Island ponies on swim day. (Lois Szymanski)

“My family and I have become really good friends with a handful of the other riders,” Matt said, counting his blessings. "If it wasn’t for them none of it would happen nor would I know what I was doing out there on the marsh.”

Last Saturday, Matt rode in the south roundup. I saw him and Pepper at the pens. I don’t know if I’ve ever seen him so happy.

“The best feeling was that first morning,” he told me. “And loading my horse on the trailer with the boys. After so many times watching everyone tack up and load up while I was left behind, that moment was the best.”

On Sunday, he rode in the north roundup. I missed this one on purpose, since it involves a nearly 4-mile hike north and then back again. We were in the throes of the worst heat this summer has dished up! But I saw Matt on Monday, bringing the ponies into the southern pens after the annual Beachwalk. This is when the northern herds, surrounded by cowboys, are walked to the southern pens against the ocean’s edge, just as the sun comes up — silhouettes against the backdrop of a surging ocean and rising sun.

“The best sight was walking the north herd over the dunes and down the beach, just so peaceful,” Matt said.

We chatted a few times throughout the week and he sent messages from time to time. He couldn’t wait until the pony swim on Wednesday. This would be the culmination of his dream.

That night, Matt sent me a photo of a feather.

“Walked out my room in the middle of the hallway sat this little beauty,” he wrote in the message. “This will be riding in my pocket tomorrow!”

I smiled when I read the message. Carollynn always said feathers were her sign that things were going to be OK. She loved Psalm 91: verse 4, which basically says the Lord will cover you with feathers and protect her. She was sending Matt a sign.

Matt had said he hoped Pepper wouldn’t hesitate when stepping onto the Saltwater Cowboy’s barge. For a horse, that’s asking a lot, but, on swim day, Pepper didn’t hesitate. He did all that was asked of him. Matt said there was a moment in time when he felt a spiritual presence.

Saltwater Cowboys, including Matt Loveland, far right, during swim day for the ponies on Chincoteague Island.
Saltwater Cowboys, including Matt Loveland, far right, during swim day for the ponies on Chincoteague Island. (Lois Szymanski)

“I remember the ponies running in the water, splashing water all over, [and then] riding through the mud and feeling like my grandfathers and Carollynn where watching,” he later told me.


My daughter, Shannon and I had risen early. For the first time ever, we had decided to see the swim from a boat. We’d signed up with some of our best friends to go with Captain Dan’s Around the Island Cruises. After countless rides with Captain Dan, he had become a friend we knew we could count on, and he did not disappoint! The ponies plunged into the water and made the swim early in the day. We saw Matt on the barge, and then lost sight of him for a bit. Then, there he was standing on the point of the marsh alongside two other cowboys on their horses.

“He’s texting,” I said, laughing. But then my phone bonged, and it was him. He’d sent a photo of Pepper’s hooves planted in the mucky marsh, and between his front hooves there was a feather. Carollynn was making sure he got the message. She was seeing his dream come true.

We laughed and watched the ponies mill on the shore. The cowboys were resting them before their parade down Main Street and into the pens at the carnival grounds where the foals would be auctioned the next day.

Then my phone bonged again. It was Karen Stannard, a friend from Connecticut. She was sending me a photo of the sky over the swim. Before I could even look up, her photo took my breath away. Two perfect feathers hovered in the sky above. The clouds had arranged themselves to become a stunningly perfect picture.

Two clouds looking like feathers over Chincoteague Island.
Two clouds looking like feathers over Chincoteague Island.

“Look at this!” I told my friends on the boat, sharing the photo. How had we missed it? Tears were filling my eyes. But there was more to come. Other friends were sending more photos. We saw how, as the feather clouds drifted apart, the sun had sent rays of light through them, creating a sundog — a rainbow in the clouds.

It was amazing! I could picture Carollynn up there, working so hard to rearrange the clouds. She was letting Matt know that she was with him. She was seeing his dream come true — a dream that she had started with the gift a tiny foal on Pony Penning day.

No one can tell me that angels do not exist. I will not hear them. What I do hear, loud and clear, are messages like this one, sent from above. I hope you hear them too.

Lois Szymanski is a Carroll County resident. Her Life & Times column, The Great Big World, appears every other Sunday. Email her at loisszymanski@hotmail.com.