Gregg Russell: The Pied Piper of Harbour Town

There are certain places that speak to us on a soul level, and visiting Hilton Head Island, South Carolina is one of those precious experiences. While the picturesque golf courses, pristine beaches, and small-town feel are a draw in itself, the real magic happens in Sea Pines Plantation, when Gregg Russell picks up his guitar under the Liberty Oak at the center of Harbour Town for children and their families. 

Gregg is a legendary musician whose career spans 47 years and counting on Hilton Head Island and beyond. He has captivated audiences of all ages with his unique blend of music, humor, and heartfelt connection. Today, Southern Character features an unfiltered interview about Gregg Russell’s life, legacy, and family.

An Island Without Stoplights

Gregg’s story begins in Birmingham, Alabama, where he grew up as one of six children in a bustling, musical household. After attending the University of Tampa and pursuing graduate studies at the University of Florida, Gregg’s musical career took an unexpected turn when he landed a two-week gig on a Carolina Lowcountry barrier island shaped like a tennis shoe–a gig that has since lasted an impressive 47 years.

When Gregg first arrived on the island in 1977, there were no streetlights, and it wasn’t even on the map. He lived out of his van behind what is now the iconic Coligny Plaza Piggly Wiggly. His luck changed when Charles Fraser, the visionary developer behind Sea Pines, offered Gregg the key to a rent-free condo and became a key supporter in building his career. What began as a short-term job quickly blossomed into a lifelong legacy, with Gregg performing under the historic 325-year-old oak tree in Harbour Town for generations of families.

A Career Beyond the Stage

His working relationship with Sea Pines developer Charles Fraser opened countless doors for Gregg. His gigs extended to ski resorts, cruise ships, college campuses, and festivals, including a performance at the 1982 World's Fair. His capability to connect with different audiences, whether performing in intimate clubs or large corporate events, became a distinguishing feature of his artistry.

His connection with the community in Hilton Head remains unparalleled. Known for his ability to make children and families laugh, Gregg’s shows are more than just musical performances—they’re interactive experiences filled with joy and connection. He often says that the real magic lies in engaging with the audience, making them feel like they’re part of the show.

The Harbour Town Lighthouse and Marina

But Gregg’s contributions go beyond music. In 1999, he and his wife Lindy co-founded Hilton Head Heroes, a nonprofit organization that provides week-long, cost-free vacations to families with children facing life-threatening illnesses. Over the past 20 years, the charity has hosted more than 1,000 families, offering them a chance to escape the stress of hospitals and treatments and enjoy a peaceful week on Hilton Head Island. Gregg and Lindy’s commitment to giving back to the community is a testament to their belief in using their talents to make a difference.

Authentic Communities

The original tape Amanda’s father found!

One of the highlights of the conversation with Gregg is his reflection on the importance of authenticity in both life and work. Whether performing for a crowd of 1,500 under the Liberty Oak or entertaining small groups on his beloved Bubblegum Cruises, Gregg stays true to who he is. His performances are as much about creating memories for families as they are about the music itself.

Gregg’s story has recently gained even more recognition through the release of an Apple TV+ documentary titled The Gregg Russell Story: If This Old Tree Could Talk, beautifully showing his nearly five decades of performing at Sea Pines and the community that has grown around his music. The film captures the essence of Gregg’s impact and offers a window into the countless lives he’s touched through his work.

Gregg’s Future Goals

At 47 years into his career, Gregg’s pace has slowed somewhat due to health challenges, but his passion remains strong. Outside of his spring and summer Harbour Town schedule, he now performs around 20 nights a year around the world, with slated performances coming up at Thanksgiving and Christmas in Sea Pines. The community's love for him is evident, and even with fewer performances, Gregg’s influence endures. As Gregg looks ahead to celebrating 50 years under the Liberty Oak, his love for Hilton Head, its people, and his music is as vibrant as ever.

For more stories of Southern resilience, charm, and character, be sure to tune in to this extra special episode of Southern Character - and pay very close attention toward the end for a musical bonus. If you haven’t yet, stream If This Old Tree Could Talk: The Gregg Russell Story on Apple TV+ to see firsthand how one man and a guitar under a tree created a legacy that will last for generations.