Daygig Painting Featured in Plantation Living’s “Notable Neighbors”

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As published in Plantation Living — December 2025

I was honored to be featured in the December 2025 issue of Plantation Living as part of their “Notable Neighbors” series. It means a great deal to be recognized in the community I’ve called home for decades. With permission, I’m sharing the article below.

Billy Howe

Bringing Funk, Flight and Fresh Paint to Our Community

If you've spent any time in Hilton Head Plantation—whether tapping your toes at a summer concert, admiring drone footage of the Pine Island renourishment, or simply enjoying a freshly painted home—you've likely crossed paths with Billy Howe. His talents span so many corners of community life that it's hard to imagine HHP without him.

Billy's Hilton Head roots go back to January 1985, when he moved to the island to join The Headliners, the well-known house band at the Hyatt Regency. For years, they performed six nights a week—suit and tie, two floor shows, and three dance sets—in the popular Club Indigo. That full-throttle musical life still shapes the rhythm of his days.

His love for the trumpet started much earlier. Around 1969, he discovered a stash of old instruments in his family's attic. His father mentioned he had once played cornet, and with elementary band sign-ups coming, Billy decided to give it a try. His parents promised lessons if he practiced every day—an early discipline that stuck. “The trumpet is a very unforgiving instrument,” he says. “It has taught me patience and dedication to a worthy goal—excellence.”

Billy Howe performing on trumpet with his band at a Hilton Head waterfront concert

That commitment shines in his work with Tower of Funk and The Choosy Mothers Horns. Led by Bill Gwynne—Billy’s close friend since 1980—the groups play challenging, joyful music with a roster of exceptionally skilled musicians. When Bill moved to the island, the two began assembling set lists of songs they’d always wanted to perform. “The music is fun and very challenging,” Billy says. “And the level of players—and friends—is outstanding.”

Billy’s trumpet also holds a special place in HHP’s Veterans Observance Ceremony. Though he did not serve, many in his family did, and playing is his way of honoring them. He is also a member of Buglers Across America, providing live buglers for veterans’ funerals and participating in local Memorial Day and Veterans Day events for decades.

This past year, he devoted countless hours to piloting his drone over the Pine Island Beach Renourishment project. What began as curiosity quickly became an artistic pursuit. “Getting to fly up to 400 feet and document the work takes photography to a different level,” he says. “Showing motion and change is fun.”

Many residents, of course, know Billy through Daygig Painting, the company he launched when his daughter was born. The Headliners were already performing more than 200 nights a year, but Billy needed a “day gig” to support his growing family. Painting soon became a career in its own right. Now off the ladder and managing the business, he often helps clients navigate the color-approval process in gated communities, where guidelines and light-reflective-value limits can make choosing exterior colors surprisingly complex.

His generosity is equally well known. Each year, Billy donates gift cards for the New Property Owners Meeting and contributes meaningfully to the Christmas Family Fund. That instinct to help is a family legacy. “My parents, Dick and Shirley Howe, were always involved in the community back home—Habitat for Humanity, helping after floods, being kind to neighbors. That’s the example I grew up with.”

Billy Howe and his wife Stacey enjoying time together on a Hilton Head beach

Billy shares his life with his wife, Stacey, a talented classical musician he first met in college at Morehead State. They reconnected decades later through a Facebook post and have been making music together ever since. Stacey has played with the Lexington Philharmonic since 1984 and teaches at Sea Pines Montessori and ARCO. On Sundays, the two perform together at the 9AM Sunday service at the Church of the Cross Chapel on Buckwalter Parkway. When she’s not teaching, Stacey loves biking, beach walks, and trying new restaurants. “We’re foodies,” Billy says with a smile.

Aerial drone view of the Pine Island Beach renourishment project in Hilton Head captured by Billy Howe

Photography is another passion. After taking a few college electives, Billy caught the creative bug and later became the 2016 Featured Artist at the Art League—an honor he describes as both thrilling and terrifying. Today, the always-handy iPhone keeps that hobby alive.

When asked what he loves most about living in Hilton Head Plantation, Billy doesn’t hesitate: “Everything!” He loves the sense of safety, the bike paths, the serenity away from tourist-heavy areas, Dolphin Head, the new pool, Lagerhead Tavern, and the Main Street shops. Favorite memories include playing tennis at Spring Lake and swimming with his daughter in the old pool with its iconic 12-foot deep end.

Looking ahead, Billy hopes to ease into semi-retirement—though with all his talents, there will be an emphasis on “semi.” He plans to continue playing with bands, performing at church, and lending his talents to musicals at the Arts Center. And in true Billy fashion, he’ll keep showing up with his trademark question: What can I do to help?

Hilton Head Plantation is all the better for it.

Originally published in Plantation Living. Shared with permission.