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Worth the Drive: Chincoteague Virginia

By South Charlotte Macaroni Kid April 26, 2021

When I was a kid growing up in Virginia, we all read Misty of Chincoteague, it was basically required reading for any middle school girl. The story takes place on Virginia's Eastern Shore in the fishing village of Chincoteague. The story revolves around a girl named Maureen and her brother Paul as they work to save money to buy one of the wild ponies at the annual pony penning. 

Each July, the firefighters on Chincoteague round up the wild ponies and swim them from Assateague Island to Chincoteague Island. These ponies are descendants of horses from a Spanish shipwreck in 1750. The pony swim has been on my wish list since I was a little girl. When we headed to DC for college tours this spring, we decided it was time to work Chincoteague into the trip. 


This small barrier island is located on the Eastern Shore of Virginia and is across the sound from Assateague Island, Maryland. Settled in the 1600's Chincoteague is known for its amazing oysters, beautiful coastline, and of course the annual pony swim. The pony swim raises money for the volunteer fire department and was started after a fire in 1925. The saltwater cowboys now round up the ponies annually and bring them over to the island. Not all of the ponies swim over, they only have the strongest swim, the others are brought over by boat. The horses are then checked out by the local vet who ensures they are healthy and addresses any health issues they may have. You can read the full history of the Pony Swim at this link.


How to Get There: The Island is only accessible by car but once you are there, you can park and walk to just about everything. 

Where to Stay: We stayed at the new Fairfield Suites. The rooms are large enough for our family of 5 and the rooms look out onto the sound. The hotel is new and was very clean and friendly. They do include breakfast with your stay which is a bonus when traveling with kids. 

What to Do: 

  • Cruise! We took our cruise with Daisey's Island Cruises, you cannot see the wild ponies without going on one of the charter cruises. We had a full boat to ourselves, the captain was amazing. We were able to bring on food and drinks (yes that includes adult beverages). They had blankets and binoculars on board for us as well. Our captain was great, he was able to find the babies for us, took us to see the bald eagles as well as the bald eagle's nests. He was raised on the island so was able to tell us as much as we wanted to know. I was of course thrilled to know he was friends with Maureen from the books and to get first-hand information about the real story. The boats go out at different times, we opted for a sunset cruise hoping it would be prime pony time as they were having dinner and settling in for the night. It was a perfect time to be out, we saw several herds of horses, the babies and even one the broke free and was in an area that he was not supposed to be in. 





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  • Shop: There are some great local shops that you can visit, the town is pretty closed down on Monday's so plan accordingly. Several places also are closed until May when they hit high season. There are several art galleries, places to buy souvenirs, one grocery store (hit a store before you cross the bridge, the store on the island was very expensive), bookstores, and a bike store. 





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  • Eat: Monday is not the night to try and eat out! We had 2 places to pick from, they were both good but we missed the places that we wanted to eat at. If you can get there, you will want to eat at Captian Zack's or Village Restaurant. These were the places our captain told was to eat at but they were not open. We ate at Bill's Prime Seafood which was good but we were sorry we missed the other ones. For sweet treats. don't miss Island Creamery or Sugarbakers! 

This is a quick trip, we stayed for a couple of days and had plenty of time to explore, see the ponies and enjoy some quiet island time.