When I was 8 years old, I read a book called Misty of Chincoteague, and fell in love. As a young horse lover, the idea that an island filled with wild ponies actually existed astounded me. Ever since, I have wanted to visit Chincoteague Island and Assateague Island, where the ponies roam. This summer, at the age of 21, I finally had a chance to visit my childhood paradise. And I got to visit with my absolute best friend… My mom.

The famous Misty of Chincoteague Island (left) with one of her foals.

The famous Misty of Chincoteague Island (left) with one of her foals. Public domain via Wikimedia Commons.

The idea

Marguerite Henry’s 1947 novel Misty of Chincoteague is a fictional children’s story based on non-fictional people, places and horses. The story follows the Beebe family and their attempts at raising a wild filly named Misty, on Chincoteague island in Virginia. The book focuses on the Beebe grandchildren, Paul and Maureen, and their love for the young pony.

Henry was inspired to write the novel after visiting Chincoteague Island for the annual Pony Penning day. The real Misty was born in 1946 at the Beebe Ranch, owned by Clarence (grandpa) and Ida (grandma) Beebe.

Marguerite Henry wanted to buy Misty to take back with her to be the model for her book. Mr. Beebe refused. He agreed to sell the pony after Henry promised to include his grandchildren Maureen and Paul Beebe in the book.


A moving book

Misty of Chincoteague won the Newbery Honor in 1948 and became a children’s classic. It is the world’s second most popular horse-themed book, after “Black Beauty.”

When I first read the book, I remember running to my mom every time I finished a chapter to tell her what happened in the story. I remember being obsessed with the idea of visiting Chincoteague and Assateague, to the point of making as many of my school projects as I could about the island.

My parents moved to Maryland in February 2016. When my mom heard from a neighbor that Chincoteague Island was “only” four hours away, she immediately remembered my childhood dream. So, when I visited my parents in the summer, she was determined to take me there.

We decided to make this a mother-daughter trip and left very early on a Saturday morning.

Me and my beautiful mom, Ana Olsen.

Me and my beautiful mom, Ana Olsen.


First impression

My mom and I had zero plans when we first arrived on the island, all I knew was that I wanted to see those famous ponies.

Chincoteague is a small town, so we had no problems finding the Chicoteague Pony Center. There, you can ride tame Chincoteague ponies whose relatives roam the neighboring Assateague Island.

24-hours on Chincoteague Island

The Chincoteague Pony Center, just before opening in the morning. Photo credit: Alexandra Olsen

Although we chose not to take a ride, we did enter the gift shop and ask the owner about her favorite boat tours to see the ponies. She pointed us in the direction of her personal favorite, Daisey’s Island Cruises. We went straight to the dock to book the tour.

When we arrived at Daisey’s dock, we were given two options: a smaller boat that left in 15 minutes or a larger boat that left just before sunset. We chose the sunset tour for $35 per person. We were told we could bring whatever food and drink we’d like on the boat. Something my mom and I were both excited about.

Where we stayed

24-hours on Chincoteague Island

The Sea Shell Motel. A view of the rooms from the pool area. Photo credit: Alexandra Olsen

After booking our boat tour, we asked the attendant, also a local, where we should stay for the night. We thought it might be tough to find a room on a Saturday night. But we were pleasantly surprised to get a room at the very first place, the Sea Shell Motel at 3720 Willow St.

This little place is adorable. Just a short walk from Main Street, it’s tucked away in a residential area. The Sea Shell also has a great little pool. So we spent an hour at the pool to cool off and relax. It was exactly what we needed after the long drive.

Our first glimpse of the ponies

After our swim, we headed across the bridge to Assateague Island to walk on the beach and see the ponies. The local who checked us in to our room told us we’d be guaranteed to see some ponies on our way to the beach.

Traveling Tip: Parking on the island is $8 per day. To avoid this fee, walk onto Assateague Island. The parking booths are the first thing you hit when driving through.

The local told us where to find the ponies. Just after the bridge are the iconic marshes of the islands. Next is a wooded hiking area. After the wooded area and before the beach, there is a clearing. This is where the herds can be spotted grazing. Sure enough, we found them.

24-hours on Chincoteague Island

The leader of the group leading his herd back into the woods. Photo credit: Alexandra Olsen

As soon as I spotted the little brown dots, I yelled for my mom to pull over (nicely), which she did with a smile. I was so excited that I nearly jumped out of the car while it was still in motion.

The herd grazed for only a few minutes before trotting closer to the road and then back into the trees. While they were still in sight, I took as many photos as I could manage. My mom took photos of me taking photos of them. Needless to say, we were both excited about getting to live my childhood dream.

The beach

After the ponies retreated, we headed to the beach, which was full of weekend tourists.

We took a short walk on the sand. The motel “concierge” advised that we leave before 4 p.m. to avoid traffic. Because there is only one road between Assateague and Chincoteague, traffic can get pretty bad. We did not want to miss our sunset boat tour.

24-hours on Chincoteague Island

A view from the boat, looking for dolphins. Photo credit: Alexandra Olsen

Choose the right boat tour

When we returned to Chincoteague Island, we picked up refreshments for our boat tour and made our way to the dock.

We arrived early to an empty boat. It did not stay empty for long. Once everyone had boarded we made our way out of the harbor and around Assateague Island.

Expect to see more than the famous ponies. Our captain told us to also keep an eye out for bald eagles and dolphins. Before long, we found one of the three large pony herds of the island.

In retrospect, we should have chosen the smaller boat. The smaller boats were able to weave into the marsh to get closer to the ponies. Our bigger boat could not.

24-hours on Chincoteague Island

Photo credit: Alexandra Olsen

Our captain knew the names of each of the ponies. That’s right, every pony on the Island has its own name. The rights to name the wild ponies are auctioned off each July during the Pony Penning Carnival. That’s a historical fundraiser for the island’s fire company that began in 1925.

Each year, the herds swim from Assateague to Chincoteague. Once there, they are paraded down Main Street into corrals where vets check each pony’s health. The youngest of the ponies are then auctioned off. Those too old to tame are named.

Iconic LightHouse

While boating around Assateague, we also got our first glimpse of the iconic “candy-striped” light house. On Sunday morning we crossed the bridge from Chincoteague to Assateague again to hike to the lighthouse. The quarter-mile hike was relatively flat. Climbing to the top of the lighthouse was the tough part. After reaching the top, we realized that the “huffing and puffing” was completely worthwhile. The view is breathtaking.

24-hours on Chincoteague Island

A view of Chincoteague from the lighthouse. Photo credit: Alexandra Olsen

Before driving back to Chincoteague Island, we stole one more look at those famous four-legged Assateague Island residents. This time, we got really lucky. Two herds showed up and stuck around. It was the perfect farewell, holding hands with mom as we watched the ponies graze.

An amazing experience

We ended our incredible weekend with ice cream and a bittersweet goodbye.

We headed first to the famous Island Creamery. This local ice cream shop has been on the island since 1975. Then, as the locals suggested, we visited Captain Chandler’s grave.

This may seem like a morbid way to end the trip, but locals assured us that this is how we could ensure our future return to Chincoteague Island.

Bonding with Mom

My mom is my best friend and my biggest supporter. She has always been there to help make my dreams a reality. She knew that we would both love this trip and that we both needed this special bonding time.

It is not often that I get to hang out with my best friend, just us two, anymore. I am now in college and she just moved to the other side of the country, making it harder for us to have our daily talks.

This short and sweet getaway was the first mother-daughter trip that we have ever taken, and it certainly will not be the last. We were enchanted by Chincoteague Island and are already planning our return.

Read the sweet story of a mother-daughter trip to visit the ponies of Chincoteague Island.

This post was written by Alexandra Olsen, a college student intern for TravelingMom.com. Her love of travel began at a very young age–traveling with her family to little beach towns growing up in Brazil. Alexandra also has her own personal travel blog, Trail Mix, which she started while spending a summer studying abroad in Norway.

What’s the best trip you’ve ever taken with mom? Tell us about it in the comments!