Shackleford Challenge 2019: exotic tales of an unfinished adventure

July 2, 2019 | Windsurfing
Shackleford Challenge 2019: Tony Vandenberg broke his mast at about 59 miles into the adventure | Photo:

The Shackleford Challenge is a 100-mile sailing marathon that kicks off in Cedar Island, North Carolina, rounds Shackleford Banks, and finishes again in Cedar Island.

It's an unsupported race with no committee boat or rescue team. You're on your own with the elements and need to find spots to rest, sleep, and cook.

Last year, veteran windsurfing marathoner Tony Vandenberg, had a close encounter with a shark. This year, "Bermuda Boy" was unlucky and snapped his mast midway through the two-day journey.

But he has a few tales to share. Here's what happened in his own words:

"I had an awesome time with eight of me hearties in Core Sound on Friday, 28 and Saturday, 29.

"Everyone made it around the 100-mile trip except your humble correspondent, who snapped his mast in half off the southeast tip of Shackleford Banks, and had to paddle back to the old checkpoint number 1.

I DNFed at about 59 miles into the adventure. And, because this year wind was really weak and all upwind, I had to push hard constantly on the leeward rail of the board to get going.

As a result of all this pressure on my feet, my big toenails swelled up and started bleeding.

Ed and Beau took first place.

Cape Lookout: the sun is rising | Photo: Vandenberg

Spanish Mustangs, Snipers and Pirate Treasures

I came across with lots of wildlife, turtles, dolphins, stingrays, small sharks, and was face to face with two Spanish Mustang Corolla wild horses, in the Shackleford Banks.

The birds on the Core Sound side of Shackleford were beautifully deafening, too.

I enjoyed great time and fellowship on the course and carousing at Sharky's Bar at the Old Ferry Terminal in the middle of nowhere.

On the 41-mile trip from checkpoint 1 to Cedar Island Ferry to get my car and broken gear back on the same team, I met an Uber driver with a curious past.

He was a retired contractor sniper, who was a history buff on Blackbeard, with tales of The Rum Keg Girl, sunken ships, and buried pirate treasures on Carrot Island.

He also shared stories of how he was present with Chris Kyle when he made that 2,000-yard long shot in Iraq.

Tony Vandenberg (right): learning more about pound nets and hearing stories of hallucinations at Sharky's | Photo: Vandenberg

Pound Nets, Hallucinations and Bourbon

On the last night at Sharky's, Ed and I ended up sitting with a fisherman that runs most of the pound nets in Core Sound.

We got to learn all about how pound nets guide the fish in, the history of the Native Americans that developed the same net techniques we use today, the types of fish, fish migration patterns, etc. Really neat stuff.

While at the same time, Seadog Rocket's Sean and Beau exchanged stories of hallucinations and drinking bourbon in stealth camping sites inside a church.

It was, once again, an awesome and fun time.

Even with Sean whining all the time like a homesick puppy about how he misses his lovely wife, Carla!"


Words by Anthony Vandenberg

The Summer Surf Gear Guide 2019