Wild ponies, seafood festivals, and some of Mother Nature’s finest sunsets…
Along the eastern shore of Virginia is a small coastal town that has often been named as one of America’s best. While part of me would like to keep it secret, part of me wants to share the love with you, dear readers.
Driving across the causeway, the familiar smell of brackish bay water floats through the windows, but once over the drawbridge, you realize Chincoteague is different. Here you will not find the towering hotels, beachfront condominiums, thrill rides or crowded boardwalks common in more commercialized seaside towns. Instead, there are charming waterman homes, artisan shops lining the main boulevard, and restaurants offering local catches.
The Seafood
For dine-in options with plenty of fresh choices, try AJ’s on the Creek or Don’s Seafood. Both offer a variety of seafood options, including catch of the day. If carryout is more your style, Gary Howard’s Seafood sells dishes prepared with seafood fresh off the boats. More adventurous visitors may want to catch it themselves — rent a waterfront home or try surf fishing at nearby Assateague Island National Seashore. We enjoy crabbing, so we stay canal-front and steam up sweet Maryland blue crabs for dinner at least once – it depends on how many we catch 😊!
The Festivals
Chincoteague respects its heritage and resources with a number of events, including the popular Pony Swim described below. Early in May the town hosts a seafood festival with a variety of fresh fish, seafood and sides, and Autumn brings the annual chili and chowder cookoff. October is our favorite event – Oyster Fest. I am NOT a fan of oysters, but I AM a fan of the big party that is Oyster Fest. Tents go up, drinks go down, games come out, and costumes go on. Island Boy gets everyone dancing, and it is just an all-around fun time.
The Ponies and the Beach
Chincoteague became more popular with Marguerite Henry’s 1947 novel, Misty of Chincoteague, the tale of one of the wild ponies on the island. Legend says the ponies were survivors from a Spanish galleon sinking off the coast. The horses swam to land, adapted to foliage and climate, and their descendants continue to inhabit the island today. Those on the Virginia (southern) end of the island are owned by the Chincoteague Volunteer Fire Department. Each July the CVFD hosts the Pony Swim, where ‘saltwater cowboys’ round up the ponies for auction with proceeds benefitting the CVFD. This event draws many visitors, so prepare for large crowds.
Beach Road is great for biking and seeing local fauna and flora – you can often spot the wild ponies, too. On the way, stop in at the Assateague Island Lighthouse and climb to the top for an amazing view out over the town and island. If you want to try clamming, there are plentiful beds, but avoid the oyster beds because they are usually privately leased. Surf-fishing is popular, and you can get everything you need at Captain Steve’s. To grab a quiet fishing spot away from the sunbathers, buy an OSV (Over the Sand Vehicles) permit and drive directly out onto the beach. Permits and reservations are also available for fires on the beach, a great vacation memory roasting hot dogs and marshmallows while the sun sets.
Speaking of the sunsets…

Mother Nature saved some of her best work just for Chincoteague.

If you haven’t gotten accommodations with sunset views, try watching it at Chinco-Tiki, a relatively new casual bar downtown. The bar offers decently priced drinks, good burgers and bar snacks, and giant-scaled games of chance and skill in the sand right next to the bay. With some luck, you may also get a visit from a playful pod of dolphins.
Downtown and more
Chincoteague’s downtown offers a number of stores to get your shop on. The Flying Fish Gallery carries items from many artists and is a great place to get some unique souvenirs. You can pick up music or a beach read at Sundial Books, or beautiful hand-crafted jewelry at Island Butterfly.
When you get hungry, enjoy absolutely ANYTHING at Saigon Village. This mother-and-son operation serves up authentic Vietnamese cuisine in quick time, and they will customize the spice level to your preference. Try the white asparagus crab soup for something a little different!
Too hot for soup? Cool down on Maddox Blvd at Mister Whippy or Island Creamery. Mister Whippy specializes in soft-serve while the Creamery offers hand-dipped happiness made on-site from locally sourced milk.
Last but not least, no visit to Chincoteague is ever complete without a trip to J & B’s. Whatever you call these sandwiches, they are some of the best we’ve ever had. Seriously, we even bring some home with us every time, they are THAT. GOOD. Go for a cheesesteak or the Italian with the hots. It’s take out only here, a great option for a beach lunch.
I don’t mean to rush through Summer – most of us have already missed out on Spring – but I can’t wait to be back on “island time” with a crab trap in the water, cold beer in my hand, and sand between my toes!
Have a favorite small-town vacation spot? Share it with us below!
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