A new order for trails in Los Angeles: Q&A with oyster expedition founder

We speak to Woodie White, the founder of Oyster Expeditions, to learn more about the outdoor group breathing new life into hiking.

Woodie White has been dedicated to his travel-inspired sports and apparel brand Oyster Holdings since 2014. The Los Angeles based brand fuses contemporary sportswear with travel-ready function, bringing new meaning to activewear. But earlier this year when the pandemic resulted in worldwide travel limitations and local restrictions, like us all, Woodie had to adapt. Not only from the perspective of his apparel brand, but also how he was to satisfy his curiosity for exploring new territories. And above all, maintaining something close to his heart – new adventures with his friends and community.

Woodie unearthed a new found love for hikes in his own city, and with a little help from friends, his creativity and an infectious positive energy, Oyster Expedition was born.

Oyster Expedition reimagines traditional hiking by infusing the very soul of California into the trips, turning them into much more than a hike – but an experience. People from all walks of life – new to trails or otherwise – join the bi-weekly hikes to soak up new spaces around LA while listening to curated playlists from the group’s DJ. Post-hike, they celebrate the workout with fresh seafood on the Californian coast.

We sat down with Woodie to hear more.

Can you tell us how Oyster Expeditions began?

Since March, with the start of the pandemic and things shutting down, that didn't leave many options as far as traveling. We were all quarantining or at least locked within our cities. We’d already been running the Oyster Tennis Club for a while by then, which is a community tennis club that we do within Los Angeles for the last, maybe 16 months or so. But with the tennis courts closed for a period of time, that wasn't an option either. So I guess that’s when I had to change my focus, not necessarily just from a brand strategy, but from a personal side of things – to get outside more.

I started with bird watching and small trails, and that built up to heading out to the Angeles Forest with a friend of mine. When you go on a hike, you have a great day, you get outside, you spend time with friends. And it’s low cost. That's one thing that I think I hope the pandemic showed people – that you should not have to spend money all the time to achieve happiness.

"I'd never really gone on any trails before. I even made the mistake of telling people on multiple occasions, I don't think I'll enjoy hiking. It doesn't seem like I get the workout I need. And boy was I wrong. This is one of the toughest things I've ever done, but also one of the most rewarding. It’s even more rewarding in a group because you're feeling it with everybody."

The first trail I went on was in a pair of moccasins and felt like I was going to slide off the side of the mountain for probably 90% of the hike. But we kept going.

How did it start growing?

We took on more trails and hikes throughout Malibu, the Palisades area, and Santa Monica. I made a suggestion to one of my favorite local seafood restaurants on one – that was the first time we connected a hike with a food concept.

But word of mouth was really a key component. I brought out a photographer on one of our first group hikes. All of a sudden we had more photos, pictures of everything on Instagram. It looked grander. The presentation was bigger, it became more appealing and official. People were paying attention and asking “What’s that?”. And then it just grew from there.

How are the expeditions looking like now?

Oyster Expeditions is now a bi-weekly group, hosting around 20 to 25 people. We want to keep things exciting and fresh for people so there's a different hike and restaurant every time. We meet on the trail at 7:30 in the morning and start around 8. One of the guys in the group is creating playlist for us each time so we have the music bumping. We bring a vibe to the mountain. It’s awesome.

Our expeditions are a form of escapism so we try to make sure nobody's discussing business. We want you to be able to come out here and get away from everything that you've had to deal with throughout the week and really let yourself go and let your guard down. I find that's what happens with myself. I get out there and I feel the best, and I have no worries. I have no cares. It's early in the morning. I'll feel like I can conquer the rest of the day after being outdoors.

It’s so rewarding to share that with people.

Why did it make sense for you to include music and food?

It becomes a full experience with food and music. It brings the vibe we want to give people.

That's the thing that's enjoyable for us is, you're playing music, you're in a group. It may be a different way than most people hype, but I feel like it's a city slicker way. When we get in a group of people, we want to play music, we want to talk, we want to have a good time. And that's noticeable when you're on the trail. When we pass other hikers, they’re like, "You're playing Stevie Wonder?”. Well, who doesn't love Stevie Wonder? Especially in the morning at 8:30.

And that reward of the meal is the thing some people are looking most forward to. I can't wait to finish so we can go eat. Because most likely, Monday through Friday, you're not going to the coast of California to eat fresh lobster, or whatever it is that the restaurant has to offer. And plus, we like the give back of bringing a group to independent small restaurants.

How would you describe the community joining your hike? Who are they?

That's a tough one because it seems to be a little bit of everybody. Most of them are inner city people but there's all walks of life.

I mean, we have hotel people, real estate, some kids, and we have designers from other clothing brands. I love that because that just shows that it's not about Oyster. No, "Oh, I can't come because I have my own brand so I can’t be seen with yours." I'm really, really happy about that. And there’s also people that I don't know what they do at all because I don't ask them. It should come from a natural place of interest, not a strategic place. LA is one of those cities where if you're out and about, you'll meet somebody and in five minutes it’s “so what do you do?” but that's not what we're here for.

It's about the community and the sport and the friendship. No ego. Anyone can join.

What are the hikes like for someone who hasn’t been on one before?

You know what the thing is, we've realized that if you let somebody know we're going to go on this trail and it’s three and a half hours or, it’s 7 or 8 miles – that sounds like a long journey for someone that doesn’t hike at all. Sometimes we mention the distance, but sometimes we don't because we don't want to scare people. Everybody's going to make the trek. They always do.

And rarely has anyone showed up alone because it feels less intimidating to bring a friend with them. But even if someone shows up alone, they’ll potentially have 20 new friends by the end.

Like you said earlier, hiking is a tough workout. How do encourage people to make it?

We go in multiple groups. We have a group that leads a faster pace. We have a medium range group, and then we have a group for people who need to take a little bit more time. As we're going on the trail, we pause at checkpoints where we can wait for the rest of the group to catch up and take a rest. It’s not a race.

I usually bring some trail bars with me just in case I see somebody struggling because you're up so early in the morning, there's a high probability that you haven't eaten. So there's people rushing out the door thinking, "I'm going to eat at noon. I'm fine." You probably won't be fine. Your appetite will kick in at some point. And if they're on the mountain struggling, I check in to be like, "Are you making it? Are you okay? All right, great." We've never had one person not be able to complete the expedition.

There’s something so rewarding about good food after a challenging hike. It must be special way to end the expedition with fresh food by the ocean.

Yeah, exactly. And you can’t really quantify the experience until the day is through. Because when you're on the mountain, you could be cursing yourself. You could be cursing me. "What am I doing up here? This is tough. When is this over?”. But by the time we get to that restaurant and everyone’s looking at the menu and the food starts coming out – all of that is gone, all of it forgotten.

"We try not to tell the location of the restaurant so that people are committed to the experience overall. I'd rather have you come on the hike and not go to the lunch than the other way around. To me, you need the hike to really be able to enjoy the reward of what's to come after that."

You know, at the end you’re just left with “woah, we just did that mountain together” and "hey, so are you come back out in two weeks? You are? Cool, I'll see you then." I love that.

So what’s next for Oyster Expeditions?

Well, I think that's where the expeditions really falls back into Oysters Holdings main mark, which is traveling as a sport. That’s what Oyster is about. One of the main reasons that tennis was always something that was part of Oyster's DNA, because it’s sport that ranked and connected globally. It’s the same with the hiking. It’s global. We can connect with anybody anywhere and do this, and it doesn't change. Maybe the terrain changes, the length and the task, but it's the same thing – the goal is just to get out.

So I think once you find the people that you vibe with, that you have like-minded interests, why not take the show on the road? I want to get the group going on Oyster expedition outside of Los Angeles. We already have some things planned. I want to plan a Santa Barbara retreat, which will include hiking and tennis at a winery. A Friday through Monday experience. And the longterm goal? Offer experiences throughout the world.

Hey, can I just throw something out there?

Go for it. We’re listening.

I will say one of my wishes…This is a grand wish. But I'm just going to say it.

I'd like to come to Switzerland and go on a hike with Roger Federer. How amazing would that be? Local LA inner city tennis club that also has a hike thing going, and they're going to go hiking with Federer.