The Good Life
with a Southern Drawl

The Best of Chincoteague Island

By Amy Bailey — May 30, 2018

It was so early in the morning darkness was everywhere except for hundreds of car headlights making their way to the ocean. Soon traffic guides would direct us down a sandy road to park and it became evident that not just hundreds, but thousands of people were there to witness the Pony Walk down the beach on uninhabited Assateague Island. Of all the things I have dreamed about traveling and doing, waking up at 3:30 in the morning on a tiny island off the coast of the Virginia to see ponies on the beach, was not one of them, but I would do it again in a heartbeat. We bundled up because even in July it is still crisp in the early mornings on the islands of Chincoteague and Assateague. We found a spot pretty easily and laid out our blanket. We chatted with neighbors and discovered that there were people here from all over the world. Some first timers, some who make the annual trip, some who come for their children, others who come without children. We waited and waited. As the sun rose children began playing in the surf laughing and chasing each other. My daughter joined in briefly but soon wanted the warmth of our blanket. There was chatter that they had rounded up the ponies and would soon be walking them down the beach. We love horses but had never seen them in a mass of over 100 together. Before your senses have time to take it all in, over 100 ponies of different ages are right in front of you within a few feet. The eyes on my daughter were as bright and wide as I have ever seen them. The Pony Beach Walk is the first event in the annual Chincoteague Pony Swim, a quirky, strange piece of American history that has been going on for almost 100 years on this tiny island, made famous by Marguerite Henry’s children’s book Misty of Chincoteague.

If you are looking for a family trip unlike any other, where nature meets American history, where the surroundings have maintained their local culture and personality for centuries, it is time to visit Chincoteague, Virginia.

Two days after the Pony Walk we would have the incredible opportunity of witnessing the 92nd Annual Chincoteague Pony Swim by boat thanks to our oyster farmer friend, Cody. When your alarm goes off at 3:30am for the second time in just a matter of days, you really begin to wonder how much you want to see wild ponies swim across a channel, but then you remember how cool all your Chincoteague experiences have been thus far and you persevere. Before 5am we loaded up the boat from the dock behind the oyster house, everyone was a little quiet and dazed including the 9 year old horse lover who was the reason we decided to travel all the way up to Virginia’s most eastern point to wild pony wonderland. We motored our way in the dark just a short distance and anchored right where the ponies were suppose to enter the water. The Pony Swim happens at slack tide which usually falls between 7am-1pm, but people begin lining up in the water and on the shore well before sunrise. We were fortunate enough to have a front row seat and I highly recommend watching from the water if you can. We watched the sunrise over the Saltwater Cowboys and did not have to wait too long after 7am to see the Pony Swim. Before you see the ponies, you hear them. A rumbling vibrates across the air, it gets louder and louder and then you see silhouettes of ponies in the distance. The sound gets louder as they get closer and soon hundreds of ponies are at the edge of the water. Without hesitation they begin to enter the water and then all you see is their heads – they are truly swimming! It is a short distance across the channel and within minutes they are climbing out of the water on the other shore onto the main island of Chincoteague. It is stunning to watch and to see the look on my child’s face, priceless. It was a delight to witness this piece of American history.

The locals say that since this has been going on for almost 100 years, that the ponies know and actually start to congregate where they will make their way across. The next day the ponies are auctioned off, many are bought but returned to uninhabited Assateague Island to live. The Chincoteague Pony Swim is a fundraiser for the island’s fire department that began after a series of disastrous fires in the1920s.

Wild ponies have inhabited Chincoteague’s neighboring Assateague Island for hundreds of years. Some have suggested that the wild ponies of Assateague trace their origin to horses released to forage on the Island by early settlers. However, the evidence strongly suggests that they are the descendants of the survivors of a Spanish galleon which wrecked off the coast of Assateague.

Horses, Oysters, and Sunsets, three of my favorite things and also the three things Chincoteague is known for. Our first experience on Chincoteague was coming over the bridge to see traffic stopped in both lanes as 20 or more ducks crossed the street. That set the stage for this travel destination where nature takes precedence.

Being a small island, accommodations are limited but there are several hotels, bed and breakfasts, and rentals. We got very lucky and discovered Key West Cottages on Chincoteague Island. Our one bedroom purple cottage faced the bay and was the perfect place to watch the sunset every night and wow does Chincoteague put on a show. The sunsets we saw from our cottage were some of the most breathtaking sunsets I’ve ever witnessed. Each cottage is equipped with a sitting area and small kitchen which was ideal for us since we love to cook. Just a 5 minute walk down the street from Key West Cottages is a health and specialty food store, Poseidon’s Pantry, which also serves to go meals. In fact our cottage put us in walking distance of many places making it an ideal place to stay to explore Main Street and the surrounding area. Not only will you find a vintage bookstore, library, boutiques, and restaurants as you explore, but also you will come across seaside seashell stands based on the honor system, $3-5 per large welk or conch shell.

Perhaps one of the most pleasant surprises of Chincoteague was the food scene. Smaller towns tend to be associated with limited restaurant choices, but not Chincoteague. There are options for everyone from the vegan to the crab fiend to the donut connoisseur.

Sea Star Cafe – Delicious healthy food like salads, sandwiches,and soups that you can take to go or eat at picnic tables outside.

Crab Shack – Want to get your blue crab fix? This is the place to grab a mallet and enjoy platters these eastern shore delicacies.

Poseidon’s Pantry – Whether you order a meal to go like the Kimchi Grilled Cheese or are looking for snacks and food to cook, Poseiden’s Pantry is fantastic.

Sandy Pony Donuts – Homemade donuts cooked to order that are absolutely the best donuts I have ever eaten.

Pico Taqueria – Serving a variety of tacos made with farm fresh ingredients and flavors, Pico Taqueria is always bustling with people.

Ropewalk – This seaside restaurant is great for the whole family and a good place to sit and unwind after a long day of pony watching.

Captain Zack’s Seafood – Great seafood baskets order to go or eat outside.

The Farmer’s Daughter – A menu full of salads and sandwiches, The Farmer’s Daughter also serves unique flavors of tea like lemon thyme, which I love.

ChincoTiki – Got to give props for such a cute name. This restaurant’s tables are in the sand. Good food, nice people, and ping pong tables to enjoy too.

Woody’s Beach BBQ – Red, white, and polka dot, Woody’s Beach BBQ serves up delicious barbecue in a fun setting.

Of all the awesome dining options, our favorite food on the island of Chincoteague was the fresh from the ocean Chincoteague oyster with a salt chaser that we got to enjoy on our tour of the oyster beds.

Whether you visit this small haven of nature and marine life during the Pony Swim or not, there are still plenty of things to do throughout the year from kayaking to fishing to museum and lighthouse tours. But the most important part of your Chincoteague vacation – enjoy being on island time. This place has so much magic to offer, relax and enjoy it.