Robbie Caponetto

Cradled between Assateague Island and the Virginia coast, Chincoteague is the smaller of the two islands and the gateway to the southern part of Assateague. The waters of Assateague Bay and the Atlantic Ocean supported island growth, and now they entice many licensed anglers to fish beaches and inlets that are ripe with flounder, striped bass, and other game fish. For some quick and easy fun, fish or crab at Chincoteague Veteran’s Memorial Park. No individual license or permit is necessary on the pier.

Once a peaceful fishing village, Chincoteague now welcomes visitors with delicious local seafood, abundant lodging, shopping, and family activities. In summer, 25-cent trolley rides take people around town with stops at the downtown shopping district, carnival grounds, community center, Museum of Chincoteague Island, and Chincoteague Chamber of Commerce

Repeat visitors often prefer fall, when most tourists and mosquitoes have dissipated. The quiet, laid-back vibe is why Northern Virginia resident Heather Swart returns several times a year. “I was looking for a place that had a small-town feel like my childhood vacation spots,” she says. “I fell in love with Chincoteague on my first visit.”

Robbie Caponetto

Wander the Trails

Hiking and biking routes help guide travelers through nearby Chincoteague National Wildlife Refuge, a utopia for birders and wildlife enthusiasts, with nearly 300 recognized migratory and resident birds. Make time to stop by the Herbert H. Bateman Educational and Administrative Center and Toms Cove Visitor Center for maps, guides, and interactive exhibits. 

You’ll climb 175 steps up a spiral staircase to reach the top of the lofty Assateague Lighthouse, but breathtaking panoramas of Chincoteague and Assateague islands from the viewing platform are worth the effort. Pause for a moment, and you might see a few bands of Virginia’s southern herd nibbling grass at Black Duck Marsh. 

Robbie Caponetto

Plan for the Pony Swim

While the small coastal community offers many family activities, all are dwarfed by the area’s most famous celebration, the Chincoteague Island Pony Swim. Virginia’s herd of wild ponies, owned by the Chincoteague Volunteer Fire Company (CVFC), grazes with permission on the southern part of Assateague Island. Each year in late July, Chincoteague’s population of about 3,000 (humans, that is) swells to 10 times its usual size as tourists and former residents make the pilgrimage to witness the event. 

Made famous by Marguerite Henry’s novel Misty of Chincoteague, this renowned festival is now a weeklong affair. “Saltwater Cowboys,” members of the CVFC who are skilled horse wranglers, move the northern herd along the Atlantic coastline during
the popular Beach Walk to join ponies in the Southern Corral. The wildlife refuge opens early that day with limited parking, so visitors and locals are encouraged to bike or hike in. 

The Pony Swim occurs on the last Wednesday before the last Thursday of July and always starts during the slack tide—a 30-minute lull between low and high tides when there is no current. Thousands of people wait for hours to watch the horses make a six-minute swim across the narrow channel separating the two islands. 

After a rest, the ponies parade to the carnival grounds for the evening. The foal auction on Thursday helps control the pony population and also provides funding for the CVFC and for veterinary care for the animals during the year. The remaining adult ponies, along with foals not mature enough to be separated from their mothers, return to their grazing grounds. 

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This storied tradition gives Saltwater Cowboy Harry S. Thorton a sense of pride. He relishes seeing his friends come together year after year for the event. “I know they love it as much as I do and work hard to keep it going. There is no other place in the world I would want to be,” he says. 

The annual Pony Penning and the popular Misty franchise are credited for Chincoteague’s successful transition from commercial-seafood producer to tourist attraction, but the area has even more to offer. 

“We haven’t missed a Pony Penning in more than 20 years, but the sunsets, beaches, and fishing are what keep us coming back from spring through fall,” says Northern Virginia resident Doreen Meadows. Her advice: “Slow down, and enjoy the town. You’re on island time.” 

Lois Heflin agrees. For more than 50 years, she has visited the islands and is now a ceremonial lighthouse keeper. “Everyone comes to see the ponies,” she says, “but then they get hooked by the beauty all around and return here.”

Don’t miss the delicious Oyster Po’boy from The Farmer’s Daughter.
Robbie Caponetto

Where to Eat

You can’t go wrong with any choice from The Farmer’s Daughter, but we suggest the Shrimp Po’Boy or Fried Oyster Salad. AJ’s on the Creek skirts the line between casual and upscale with tables covered in crisp white linens and topped with paper napkins and bottles of hot sauce. Seafood lovers can find the best of the Eastern Shore here. Seasonal soft-shell crab is served fried on platters, and a romaine salad is transported into sublime territory with a zesty citrus Caesar dressing, Parmesan crumbs, and crisped bread.

Robbie Caponetto

At the popular Pico Taqueria, the inventive taco menu encourages hungry diners to try several, such as The Eastside (fried fish, fennel, and grapefruit salad drizzled with avocado cream) or The Maddox (local fried oysters topped with pickled carrots and Thai basil). Their modest pricing makes it easy to experiment with different options. When it’s time for dessert, you’ll discover the reason for the long line of people queued up at Island Creamery. Their small-batch ice cream and homemade waffle cones are a national phenomenon and an island treasure. Go online to see dozens of daily flavors.

Where to Stay

Hotels situated along Main Street are within walking distance of shopping, dining, and trolley stops, and many of them also offer visitors some beautiful sunset views across Chincoteague Bay. The Island Resort, Waterside Inn, and Marina Bay Hotel & Suites are all great options for travelers.

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