Winter in the Outer Banks has a way of settling in quietly, and for many people it brings more than colder temperatures and shorter days. Once the holidays pass, there's often an emotional and financial strain that shows up, especially in a seasonal, resort-based community like this one. Work slows down, businesses feel the shift, and the outdoor lifestyle that draws so many of us here isn't always as easy to access when the weather turns, which can make the offseason feel heavier than expected.

I also want to share a quick update on the podcast. After a bit of a technical pause, I'm glad to be back and moving forward again, with plans to bring more local voices into the conversation as we head into the coming months. Sometimes an unplanned reset is part of the process, and I'm feeling optimistic about where things are headed and the stories that are still waiting to be told.

Just before Christmas, I had one of those experiences that reminds me why the Outer Banks are special year-round. I paddled out alone on a rare calm winter day, surrounded by dolphins, when a massive humpback whale surfaced nearby. I followed it for nearly forty-five minutes as it fed, blowing bubbles and drawing in birds, fish, and more dolphins. Moments like that are humbling and grounding, and they're a reminder that even in winter, this place still holds a quiet kind of magic.

In This Episode:

• [00:03] Winter is settling into the Outer Banks, and life changes after the holidays in a seasonal, resort-based community.
• [01:15] Short days, cold weather, and constant wind can make winter feel heavier, especially for people who moved here for the outdoor lifestyle.
• [02:30] The holidays are joyful, but the financial strain that follows can be magnified when most income depends on the summer season.
• [03:28] Many local businesses shut down for months, and money gets tight for residents who rely on seasonal work.
• [04:24] Even in winter, getting outside matters, and some of the most meaningful moments happen when you least expect them.
• [05:59] A rare calm winter day before Christmas creates the perfect opportunity for a solo surf session.
• [06:32] Surfing in winter means cold water, heavy wetsuits, and conditions that feel like a cold plunge.
• [07:21] Dolphins surround the lineup, adding to an already special day in the ocean.
• [08:36] Increased activity in the water draws attention, with birds and fish signaling something unusual nearby.
• [09:19] A massive humpback whale surfaces close to the surfboard, turning a quiet session into a surreal encounter.
• [10:50] Remembering a past sunfish encounter explains the instinct to paddle closer rather than away.
• [11:26] Following the whale at close range reveals dolphins gathering around what feels like the leader of the pack.
• [12:08] The whale's presence dominates the water, disappearing and resurfacing in unpredictable ways.
• [13:01] An unexpected smell raises awareness of just how powerful and alive the ocean environment can be.
• [15:45] The experience becomes one of the most humbling moments ever in the water.
• [17:10] Why the Outer Banks remain special year-round, even in the quiet winter season.

Resources:

Beach Road Banter Podcast

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