This year, riding a bike on unpaved Howard Street was precarious because of the deep ruts. Many homes on Ocracoke are still under reconstruction after Hurricane Dorian devastated the island in 2019, so I’m sure the truck traffic doesn’t help the condition of the street.

Calling it a street is misleading, though. It’s really a one-way lane, and it holds a rich history.

Ocracoke

For more than 300 years, pirates, sailors, castaways, renegades and other eccentrics have made Ocracoke Island their home. If you’ve never heard of it before, Ocracoke is the last island in the string of narrow islands called the Outer Banks on the eastern edge of North Carolina. There is no beachfront development on the island because 90% of it is owned by the National Park Service.

William Howard the pirate

As the story goes, William Howard was Blackbeard the Pirate’s quartermaster, which means he was the chief operating officer of the ship. Luckily for him, he had just left that job when Blackbeard was killed off the coast of Ocracoke in 1718. Howard went to Virginia where he was pardoned for piracy by King George. Howard returned to Ocracoke and bought the island in 1759.

In 1835, a foot path on the North side of Cockle Creek, from “just North of Thomas Bragg’s House” to “John Pike’s garden” was mapped. Residents walked barefoot through the ruts left by horse-drawn carts. Sometime in the 1950’s, Stacey Howard nailed a wooden sign on a tree in front of his home that declared the road East Howard Street. 

Take it slow

Today, the narrow road is still unpaved, but it’s been stabilized with shells and gravel.

The Howard family is now in its 10th generation of living on the island. Their ancestors’ cemeteries and those of other early settlers are surrounded by moss-covered wooden fences and gnarled live oak trees lining the road.

Also you’ll find the Village Craftsman, one of my favorite shops on the island, nestled among the homes. The store is run by Phillip Howard, a historian, author and blogger on all things Ocracoke, and pirate William Howard’s descendant. And he’s a really nice guy.

I hope you enjoyed this trip down Howard Street. There’s so much to love about Ocracoke. Every time my family visits, we discover something new.

My forthcoming novel, Love and Other Incurable Ailments, is set in Ocracoke. It will be published by Regal House Publishing in fall 2026. Please sign up for my newsletter for updates.

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Thank you for visiting.
Linda K. Sienkiewicz is a wrangler of words and big messy feelings in fiction and poetry.
In the Context of Love | Gordy and the Ghost Crab | Sleepwalker
Love and Other Incurable Ailments, coming 10/27/2026 from Regal House Publishing
Connect with Linda on social media: LinkTree