—David Menconi, Down on Copperline
When it comes to singing sea chanties, the appropriate setting seems like it would be aboard a ship at sea – or at least close enough to the ocean to smell the salt water. Given that it’s close to 200 miles inland from the Atlantic Ocean, the Orange County town of Hillsborough doesn’t seem like the most ideal hotbed for chantey-singing. Nevertheless, it has enough of an active local chantey-singer population for several dozen of them to gather the second Friday of every month at Hillsborough’s Colonial Inn for a monthly Chantey Pub Sing.
The local organizers are Dani Black plus Jerry Bragg and Laura Bradford of the folk-singing duo Thunder and Spice, professional musicians who also perform Celtic, folk and renaissance-fair music. Hillsborough’s Chantey Pub Sing happens under the auspices of Ship’s Company Chanteymen, a 501(c)(3) non-profit based in the Baltimore/Washington, D.C., area.
Established in 1996 as a musical spinoff of the group’s living-history reenactments, the Ship’s Company Chanteymen have a regular series of monthly singing events mostly around Maryland and Virginia. The Hillsborough sing started about two years ago, and it is the group’s farthest South venue – and also the farthest inland.
They set up shop in Hillsborough primarily because the Chanteymen’s founding co-leaders both have ties to the area despite living elsewhere. A retired Navy veteran, Michael Bosworth has a daughter with two of his grandchildren living in Hillsborough. That’s a good draw to get him down from Vienna, Va. Another draw is Bosworth’s co-leader Jim Rockwell, who lives about an hour away in Smithfield.
“I was looking for a way to see Jim more often, and the grandkids are an easy reason to want to visit,” says Bosworth. “I’m not a poor man but I am a cheap man. ‘Frugal,’ I say, and what’s better than singing with buddies, visiting grandkids and getting reimbursed for it? So I come down every month or two.”
The Hillsborough events tend to draw somewhere between 15 and 30 participants, typically arrayed in a circle with different people taking turns leading the group through maritime music and work songs. As kids are often part of the crowd, it’s family-friendly and participants are urged to “Save the filth and bawdry for the after party.”
As for repertoire, sea chanties tend to be call-and-response work songs with a regular, heavy rhythm and possibly dozens of verses. They’re essentially sea-going versions of chain-gang work chants. The Hillsborough group has a “chantey hymnal” songbook available for $5, filled with songs both popular and obscure. Well-known vintage chestnuts like “Sloop John B,” “Drunken Sailor,” “The Wreck of the Edmund Fitzgerald” and the “Gilligan’s Island” sitcom theme do come up, but a handful of newer songs are entering the rotation, too.
“The Hillsborough event is nice because there’s a pub attached, so you’re able to have an adult beverage,” says Jerry Bragg. “And we actually have some young people showing up who know the music from the gaming world. ‘Wellerman’ is one song people know through the ‘Assassin’s Creed’ game, a popular song online during the pandemic when everybody was stuck at home.”
As for the overall vibe of the Colonial Inn events, the organizers do their best to keep things informal. Participation is welcome and encouraged, but not mandatory.
“I liken it to building a sandcastle,” says Bragg. “You sing something and then it’s over and done with, but you’ve created something in those few minutes. Then you move on to the next one. It’s a very welcoming, safe, supportive environment for anyone who isn’t too comfortable singing in public. It’s just something we do for the sheer joy of it, keeping the historical thread alive while also keeping it entertaining and light. There’s a very traditional human need to sit in a circle and sing, which can seem lost these days in a world where everybody’s on their own headphones.”
Chantey Pub Sings happen 7-9 p.m. the second Friday of each month at the Colonial Inn, 153 W. King St. in Hillsborough, organized by the Ship’s Company Chanteymen. The next one happens on Jan. 9, 2026.
