Will Holmes on Surf, Community, and Why the Outer Banks Still Feels Like Magic | #42

Growing up on the Outer Banks shapes a person in ways that are hard to fully explain unless you’ve lived it. Today’s episode taps into that local heartbeat through someone who embodies the true spirit of this place: Will Holmes, a lifelong OBX native who grew up in Chicahauk in Southern Shores, surrounded by salt air, bikes on the paths, and a tight-knit community of friends who are still connected decades later. His story is full of nostalgia for a time when kids spent sunrise to sunset outside, knocking on doors, riding bikes, and living life without screens in their hands.

Will has spent every summer of his life on the Outer Banks, and he knows the hustle it takes to build a life here including working in numerous local restaurants, catering, surfing, and doing whatever it takes to stay rooted in the community he loves. His energy is contagious, and he’s passionate about supporting the next generation, celebrating local talent, and embracing the changes shaping the Outer Banks, from Manteo’s evolving scene to the growth of local businesses and creative culture.

We also talk about Down the Road, the surf-art-music festival Will co-created with my son Ryan, which has grown from a backyard gathering to a signature fall event held every second week of October. And we’ll hear about Will’s next big chapter of splitting his year between the Outer Banks and Puerto Rico to chase waves, build community, and create a place where friends from all over can come together. I’m excited for you to experience his perspective, his positivity, and his deep love for this special place we call home.

In This Episode:

• [01:04] Will shares what it was like growing up in Chicahauk, a tight-knit Southern Shores neighborhood.
• [02:48] He talks about the freedom of childhood before cell phones and the lasting friendships formed.
• [06:50] Will describes his family roots and how his dad spent summers on the Outer Banks in the 1950s.
• [07:18] Discussion about the population changes and remote-worker influx after COVID.
• [08:54] We reflect on development and how the community has evolved without losing its spirit.
• [09:38] Memories of SeaMark and other iconic Outer Banks spots that have disappeared over time.
• [09:52] Will explains how he discovered his passion for the restaurant industry and culinary school.
• [11:27] The year-round work cycle and seasonal employment hustle of the Outer Banks lifestyle.
• [13:43] Will shares his role at Olives in Manteo and what he loves about the town’s recent growth.
• [15:01] The housing challenge for young locals and why he ended up living in Manteo.
• [16:36] Talk about new restaurants, breweries, and small businesses raising the bar along the OBX.
• [19:23] The Outer Banks hustle: two jobs or two houses if you want to make it here.
• [20:59] A conversation about storms, off-season boredom, local resilience, and the unique rhythm of island life.
• [23:34] Will describes the story behind Down the Road, the surf-art-music festival he and Ryan created.
• [25:47] Even in bad weather, the community showed up and young surfers kicked off the event.
• [27:02] The second week of October will remain the annual date for Down the Road.
• [28:48] Will reveals his next chapter: splitting time between the Outer Banks and Puerto Rico to surf and build community.
• [30:03] His dream of creating a surf retreat in Puerto Rico where friends can come stay, surf, and connect.
• [31:26] Watching Will charge big waves at Tres Palmas and how powerful the moment was.
• [33:05] Will talks about cooking and connecting with people in Puerto Rico, serving food oceanside.
• [34:04] Invitation to explore Manteo, support local businesses, and mark calendars for Down the Road 6.

Resources: 

• Willy’s Family
• Down the Road Surfing