A month into funemployment, I wanted to take advantage of shorter adventures that were close by and affordable (like my visit to TALA in West Virginia). I immediately thought to start with seeing the Chincoteague ponies, which was on my bucket list of places to see. The only place I’ve ever seen wild horses was out in Corolla, North Carolina, and I wanted to see more!
And so, I planned for a quick day trip out of seeing the ponies and exploring Chicoteague, Virginia. Read on to learn more about Chincoteague and its ponies, and my summer day trip to Chincoteague.
Chincoteague (Assateague) Ponies
Chincoteague ponies are small, tough horses that have adapted to life in the wild on Assateague Island, off the coasts of Virginia and Maryland. They’re also commonly called Assateague ponies or horses. The names can be used interchangeably depending on their location and management.
The Virginia herd is managed by the Chincoteague Volunteer Fire Company (e.g., Chincoteague horses), while the Maryland herd is managed by the National Park Service (Assateague horses). Both herds are the same breed, but the Chincoteague herd has more genetic diversity due to occasional crossbreeding.
History and Origins of the Ponies
No one knows for sure where the ponies came from, but the most popular story is that they’re descendants of Spanish horses that swam to shore after a shipwreck in the 1500s. Another theory is that early settlers brought horses to the island to avoid paying livestock taxes or building fences. Recent DNA evidence gives some weight to the Spanish shipwreck explanation, linking the ponies to early colonial Spanish breeds.
The tradition of “Pony Penning Day” dates back to the 1830s and was formalized in 1924 as a way to raise funds for the local fire department. The event still happens today, when the ponies are rounded up, swim across the channel to Chincoteague, and are auctioned.
Chincoteague vs Assateague Islands
Assateague and Chincoteague are two separate islands, though often closely linked. Assateague is an undeveloped barrier island, home to the wild ponies, beaches, and protected parks like Assateague Island National Seashore and Chincoteague National Wildlife Refuge. Chincoteague on the other hand, is just west across Chincoteague Bay. It’s smaller, more developed, and has shops, restaurants, and plenty of places to stay.
Every July during the Pony Swim and Pony Penning events, the “Saltwater Cowboys” round up the ponies from Assateague across the channel to Chincoteague, where they’re auctioned. That’s why the ponies are often associated with both islands, even though their real home is Assateague.
Options for Seeing the Ponies
There are several ways to see the Chincoteague/Assateague ponies, the most popular being boat tours.
Boat Tours
Boat tours are the most accessible way to view the ponies grazing in marshes, as guides know the best locations and can provide close-up views. These tours leave from Chincoteague and take you around both Chincoteague and Assateague, giving the best chance for pony sightings (as well as dolphins and birds!).
Kayak & Paddleboard Tours
Guided kayak and paddleboard trips are also available, but you can also rent kayaks and explore on your own (and of course keeping a safe distance from the animals). If exploring on your own, Donald Leonard Park, Veteran’s Memorial Park, and Queens Sound Boat Ramp are recommended places to launch.
Hiking & Biking
Ponies can sometimes be seen when hiking or biking the trails through Chincoteague National Wildlife Refuge, like the Wildlife Loop and the Service Road. Some routes might mean hiking several miles into restricted areas, so it’s not as guaranteed to see ponies this way. Please also bring lots of mosquito repellant as bugs can get really bad on trails!
Bus & Specialized Tours
The Chincoteague National History Association offers seasonal Refuge Trek bus tours, providing access to areas closed to private vehicles.
My Trip to Chincoteague
I wanted to maximize my chances of seeing ponies, so I looked for guided boat tours where tour operators would know exactly where to go to see ponies. After browsing a few options, I settled on Daisey Island Cruises, which is a family-owned business that offers tours year-round.
They offer a number of different tour options, but since my main goal was to see ponies, I opted for the “Ponies Only” tour. It’s possible we would’ve also seen dolphins and other wildlife (we did see a bald eagle! And a splash of a dolphin), but the main goal was to see ponies! Pony tours are offered at 6am and 2:30 pm. Since I’m an early bird, I chose to do the 6am tour. Note that if there’s not at least 3-4 people on the boat, the tour will be rescheduled for another date when there are enough people (which is what happened to a couple that was on the tour with me).
Daisy Island ‘Pony Only’ Tours:
- Tour times: 6 am or 2:30 pm
- Cost: $65 + taxes (adults); $55 + taxes (children)
- Tour length: Approximately 2 hours
Staying in Maryland the Night Before
Since the pony tour I booked was at 6am, I stayed the night closer to Chincoteague so I had less of a drive. I stayed the night in Pocomoke City, Maryland, which is about 30 minutes to Chincoteague.
I arrived in the afternoon to grab an early bite to eat and then checked in to my Airbnb. Then I got ready for bed early since I would have to be up by 4:30 am!
If I had more time, I would’ve explored more of Pocomoke City, like the Delmarva Discovery Museum, which is a hands-on museum on the Pocomoke River, with exhibits on the history, culture, and environment of Maryland’s Eastern Shore. They also have live otters!
Things I prepared to take with me on the tour the next morning
- A bottle of water
- Light jacket since we’d be on the water
- A cap
- Sunglasses
- Hair tie
- Sunscreen
Next Day Early AM Chincoteague Pony Tour!
My alarm woke me up at 4:30 and I promptly left by 5 am to get to the boat dock by 5:30 am. From my Airbnb, it was a dark and windy path to Chincoteague, and very few people on the road. I wanted to get there early enough to make sure I was in the right place.
Once I got there, I parked my car and waited by the dock for others to get there. I knew I was in the right place because there were pontoon boats with the Daisey Island Cruise name on them (right across from the Harbormaster building).
The guide arrived to meet us on the dock and he took us out on one of the pontoon boats. The boat was really spacious and comfortable, and we had a lot of room. It was just starting to get light out as we headed to a marshy area. It wasn’t long before we started to see ponies in the distance.
We were able to get deep into the marshes and get very close to them. It was really magical to watch the birds and ponies as the sun began to rise above the trees and water. Our guide took us to a number of spots to see ponies, and he parked the boat at each spot so we had time to observe, ask any questions, and take photos. We didn’t feel rushed at all.
While we observed the ponies, our guide shared more about the history of the ponies, Chincoteague and Assateague, and stories about the names and personalities of the ponies themselves.
The time flew by and before we knew it we were back at the harbor at around 8 am. The harbor where boat tours launch is located at the southern end of Chincoteague Island, which is a bit removed from the Historic Main Street area, so it was another short drive to get there to start exploring.
Exploring Downtown Chincoteague
Ponies were my main goal, but I wanted to make the most of my remaining time in Chincoteague before leaving in the afternoon. Here’s how the rest of my day unfolded:
AmaRin Coffee
Most places didn’t open until around 10 am, so I had some time to kill. I decided to use that time to grab a coffee and apply to some jobs in the meantime.
Morning at AmaRin was CROWDED! I was there in the summer, so of course it was crowded, but I didn’t expect the line to be out the door. There were a number of tables inside still available to sit at, so I still waited in line. Most people seemed to be taking their coffees to go, or choosing to sit in the outdoor seating area. There is a credit card surcharge if using credit, so consider bringing cash. Note that I think there’s also a drive-through, so if you park in the back, it can be challenging to navigate getting in and out of the parking lot during the morning rush.
I ordered a black coffee (much faster than any other fancy drinks) and made my way to an empty booth to do some reading and apply to some jobs. They also serve bubble tea and various pastries! A lot of people were ordering croissants while I was there so they must have been good.
Robert N. Reed, Sr. Downtown Waterfront Park
At around 10:30 am I walked down to Robert N. Reed, Sr. Downtown Waterfront Park which has picnic areas and benches alongside beautiful views of the bay. Down at the park there is also a known “LOVEwork” installation featuring giant Adirondack chairs, which is a popular spot to take photos! I walked around, took photos, and read a book outside.
Exploring the Remainder of Historic Main Street
My next stop was to visit Sundial Books, which is a locally owned bookstore with two floors of new, used, and collectible books.
Then I headed to The Chincoteague Island Library, also known as just the Island Library. It’s a small, independent public library that serves the residents of Chincoteague and Eastern Shore communities. It is free and open year-round, staffed mostly by volunteers, and supported by donations and grants.
The library was one of the cutest I’ve ever seen! The inside felt more like a coastal cottage than a traditional library. There’s lots of sunlight from tall windows, hardwood floors, and shelves of books all along the walls. Comfortable armchairs are placed throughout the library for visitors to sit and read at. When I first entered, there was also a table dedicated to puzzles for people to work on, which I also thought was really cute.
There were many other little shops I explored until I decided to stop into Don’s Seafood Market & Restaurant for lunch (recommended by many!). I ordered a half dozen fresh oysters and then fried clams. Both were fantastic! Another option I considered from recommendations was Bill’s PRIME Seafood & Steaks.
Island Creamery Before Heading Home
I know my main goal was to see the ponies, but if I were to visit Chincoteague again, Island Creamery would be an absolute must-do. Had I known how good it was, I would’ve brought an even larger cooler to take back more ice cream with me.
I read that some people went to the creamery everyday throughout their stay in Chincoteague. Many recommended it as a top place to go (and I would agree!). Our Pony Tour guide even replied with “Island Creamery” in response to the question, “What’s your favorite spot to eat around here?”.
The creamery has been family-owned since 1975, and has a variety of unique and classic flavors like Pony Tracks, Almond Joy, Java Jolt, Cantaloupe, and Black Raspberry. All waffle cones are made fresh on-site. There’s indoor and outdoor seating on a patio as well.
I’ve heard the creamery can get crowded, so the best time to go is earlier around lunch time or in the early afternoon. When I arrived around 1pm there were people there, but there was no line. However I could tell though that when it got busy, that the line would be really efficient.
I called ahead to order flash frozen pints to take to go, and also got a cup to try. I don’t think they let you order flash frozen pints in person, so it’s important to call ahead and let them know what flavors and when you’ll pick them up.
As far as flavors go, I would recommend Pony Tracks and Cantaloupe! Black Raspberry was good too, but my least favorite of the 3 flavors I tried.I wish I could’ve tried the Java Jolt. And many other flavors, of course.
Future Considerations: Planning a Visit Around a Rocket Launch
One thing I wish I had more time to do is to plan my dates around being able to see a rocket launch. Rocket launches happen on nearby Wallops Island, and include both NASA and commercial missions, typically using small to medium-size rockets. These flights carry everything from research experiments and new technology tests to small satellites and even sounding rockets that study Earth’s atmosphere and space.
Rocket launches from NASA’s Flight Facility can be viewed from Chincoteague. You can go to the Wallops Visitor Center to view launches on the bleachers there (it’s about 4 miles from the launch pads), but arrive early as space may fill up quickly. Apparently it is also possible to see the rockets from Chincoteague at Robert N. Reed Downtown Waterfront Park
Launch schedules can vary throughout the year, but you can see the latest planned launches from their website. The launches are subject to change due to weather or technical issues though, so it’s not guaranteed that what shows on the calendar is the day it will happen. If you have time to stay a few days, you might be able to catch the rockets if they are rescheduled!
Final Thoughts
Taking this day trip to Chincoteague was so worth it and reminded me how rewarding it is to make time for small adventures. A month into unemployment, I’ve been filling my days in different ways, but this was a chance to do something I might have pushed aside when work was busier. Watching the ponies at sunrise and taking in the charm of a little island town left me with great memories. I hope I’ll keep finding ways to make the most of where I am in life right now.
