WinterWonderGrass started off as a singular music festival experience held in a beautiful mountain setting in Steamboat, Colorado, that brought together roots musicians, audiences, and communities focused on creating a particular atmosphere. That atmosphere included families, local businesses like breweries, and musicians who were as fond of the outdoors as the attendees.

Over the course of eleven years, that event has not only endured, but expanded considerably to other carefully chosen locations and experiences. Coming up next week, between April 24 and 26th is 2024’s Baja, California festival, BajaWonderGrass, bringing that vibe to a beachy setting. This summer through autumn, there will be several river events that take travelers on several days of rafting in Utah alongside accomplished musicians who will perform along the way.

I spoke with founder and CEO Scotty Stoughton about the original goals of the event, its expansion, and the crazy moments that seem to show just how special WinterWonderGrass can be.

Hannah Means-Shannon: Having run these events for eleven years, does it get easier over time to run them smoothly?

Scotty Stoughton: I think it gets easier on some of the tactical stuff, but it gets harder to always demand that we improve all the time. That’s difficult. On years one, two, and three, there’s so much energy and people are so excited that they let you slide on some things, but once you’ve been doing it for ten or eleven years, you have to think about how you book people, what your drink prices are, and it’s got to keep improving. That’s a beautiful challenge. We don’t always succeed, but then we happily fail and we learn.

HMS: Your progress has also been towards expansion, so I imagine that once you’ve gotten a handle on one thing, you’re looking towards adding another thing. You keep setting new challenges for yourself.

SS: Definitely, and the goal for us has never been to expand to expand. It was quality over quantity and the nature of the event and the environment dictating what was next. When I was out in Baja, that happened because I saw this gorgeous piece of land, and I asked the community, “Do you want some Bluegrass?” And they said, “Yes! Let’s do it!” It was a great spot that I felt good about, so that’s how it happened. The same happened with the other events.

HMS: I was wondering about how locations get chosen, which you’re touching on. Is the first thing about whether the local community wants to come out and be the audience? Is that foundational? Or do you also build on hoping audiences will come from further away?

SS: Absolutely. I’m a firm believer in making sure that whatever I do and wherever I go feels good from the inside out. That starts with you, and making sure that you’re doing things with integrity and clear intentions. Then you find the places that you feel supported in. Even, spiritually, I’ll ask the land. I’ll sit there and meditate on the grounds, or on the beach, and ask, “Is this right? Does this make sense? Will this impact be more positive than negative?” That’s really crucial for us at Bonfire [Entertainment]. We’re making sure that people most impacted by the event really want it and feel good about it. Then, where there’s a lot of love, people want to come there.

I’ve seen a lot of festivals go in and jam them down communities’ throats. Things don’t work out like that.

HMS: Yes, that’s a really well-known phenomenon. It’s like tourism, that brings in a lot of opportunity for local businesses, but you can also create a lot of stress. I can see what you’re saying about making sure there’s a structure there to handle the influx of people and making sure that the people who will be impacted want to be part of things.

SS: Absolutely. It’s also about presenting your case and being passionate, but not forcing things on people. I’ve seen a lot of that as I get older and watch growth, whether it’s real estate, gentrification, or a festival. I’m not sure why they don’t listen to the community first. Well, I know why. It’s because they might get an answer that they don’t want to hear! I take that answer and say, “Okay, that’s what goes.”

HMS: Have there been places that you’ve considered that turned out not to be the right thing?

SS: Actually, no. But I think that’s because when I come in to talk to people, I’m very transparent, and I’ve already done my research. Also, I throw rootsy, Bluegrass kind of stuff that’s fairly low-impact. Back 13 or 14 years ago, I was a partner on a big festival that had a lot of Electronic music that was big for the community. It was too big for the community and I watched that process. It didn’t feel very good to not be welcome somewhere. We moved it and ended up stopping it, though it was successful. That happens.

HMS: It sounds like that became a key experience for you in what you’re doing now. Sometimes we learn a lot when things don’t go right.

SS: Yes, absolutely. And that’s okay.

HMS: Something that makes these events different from what I usually see or go to is the family element. A much smaller proportion of festivals are family-friendly than those which aren’t. Some are kind of in-between. Kids can come to Willie Nelson’s Outlaw Country Music Festival, for instance. But does having a family focus help with integrating into the community, too? That way you’re not excluding part of the population.

SS: For sure. It’s fun. Kids bring such a great energy. I’ve had kid zones at festivals since before I had a kid. I love the energy of kids running around. It’s a very grounding effect. Even when there’s people partying, it sets the tone that this is a community. It’s about showing respect and being kind. Bringing a large element of family to the festival is so much fun, and we can see these kids growing up over many years. Coming to the festival profoundly affects them. If we can set examples of how we want our kids to be, that’s better for our future. I don’t care if that effects the “party vibe”. Our kid zone is front and center.

HMS: Is there an origin story for the idea of starting WinterWonderGrass? Was it an epiphany for you? Needless to say, not many people would start a music festival in winter weather.

SS: I grew up in New Jersey and I spent my days driving six hours up to Vermont with my parents, God bless them. This was in the 70s and 80s and I found this beautiful mountain culture of people gathering on the hill, everyone would know that you’d meet up at the base at four o’clock. When you met at the base, everyone would have their own adventures and own stories. You’d get there, and there would be people grilling on a big BBQ, people drinking beer, people picking music. Everyone would be having these beautiful conversations. If the snow started falling, people would get more excited, since it’s a beautiful thing for those of us who loved the mountains. That just stayed with me.

Moving out West, the culture is different. It’s a mega-thing. There are big resorts. When I wanted to design Winter Wondergrass, that really stayed with me. I asked: How do we create that end-of-the-day feeling on the mountainside that really feels like a great place to share stories and listen to music? That was one part. Then, I was living in Colorado, and I love the mountains and winter. I’d been to a lot of winter World Cup events outdoors. Then I’d see a pop-up of a band playing in the winter. I started to think about combining these elements. Bluegrass fans love mountain culture. Mountain folks love Bluegrass and Roots music.

The thread is, you’ve got to be a little nuts! You’ve got to find ways to play in a blizzard! We designed ways to keep the stages pretty warm. We’ve got four tents on-site that host three side-stages. There’s a main stage outside. We just prepare really, really well. We market this as, “WinterWonderGrass—It’s not for everybody.” It’s not! You need to prepare and plan, and be ready.

We had a blizzard this year in Colorado. It snowed three feet in three days! To watch the bands going out there to play, laughing, and see the snow crew shoveling snow off the stage, it was so unique, so magical, so beautiful, and so insane. It worked!

HMS: Having those heated tents is a big deal. That might be a big decider for people who love the winter but, realistically, don’t want to get frostbite. Is that the major expense for you, to keep things heated?

SS: It’s a massive expense. We try to keep our tickets reasonable, but our ticked price is $249.00. Each day we have a beer tasting for three hours from local breweries. Who gives away free beer at a festival? But there’s the heating, and there’s also our green team that takes everything away. To clean up after every event takes days and days. We spend a ton of money to create a magical experience, but I’m very price-conscious. You’re supporting 25 bands with over 20 hours of music.

HMS: I think you’re right that in mountain communities, there’s a natural connection to Roots music. I actually came across your events because bands I support were posting about playing with you, like Kitchen Dwellers. A lot of these bands are actually very outdoorsy people, like Leftover Salmon, Greensky Bluegrass, and others. I’m not surprised that they were up for this. How do you approach bands?

SS: Luckily, I got into this Producer/promoter career in the late 90s. I was touring with a Punk band, playing with Primus, and I was in the studio with Eminem. I was really close to getting a big record deal, and I came from the world of touring, and driving, and promoting. In those days, I met a lot of different bands. Leftover Salmon was one of the first, and I flew around the country sitting in with them. I started meeting more and more people, and the thing that resonated with me about the Bluegrass community is that they really care about each other and about the crowd, and they are always willing to share the stage with other musicians. That felt right, to give up the spotlight.

As I continued my journey, I was booking small events in Colorado. I started booking some of these guys 15 years ago, like Greensky Bluegrass. Then I started creating my event, and I called my friends. I said, “I’ve got a crazy freakin’ idea!” They said, “Let’s go!” I have never yet had one artist who refused to come back. I’ve had big time artists play in a blizzard, and that says a lot about these artists. People ask me how I choose these bands, and I say, “They have to be able to play when the lights go out.” They can’t freak out. They have to be pure entertainers who can deal with adversity.

HMS: There are those people in music! Also, because they’ve played in every kind of venue, they have that “nothing stops the show” attitude. What happens at your river events? I’ve seen some of these bands taking part in those.

SS: You come off of them saying, “That was the greatest event of my life, pinch me!” It’s indescribable. People book the trip for four days and three nights, and they have to get to the middle of nowhere in Utah. Everyone’s nervous. You meet us at the boathouse at seven in the morning, and you get dry bags and gear, and get thrown into these vans. Sometimes your favorite artist is sitting next to you. Then you get put into the river and we float for four days through these beautiful, remote, empty canyons with private beaches to camp on. You’ll hear performances from these artists, either on a raft, or up next to a waterfall, or perched on a rock.

You’ll wake up to them playing the flute while you drink hot, fresh coffee, or you’ll hear how they wrote a song while you prepare your day to go hiking. Then you swim and share these amazing organic meals. It’s a lot of purpose. It’s not so much a party. It’s a serious location where you have to be careful since you’re very remote. But it’s an opportunity to get back to what it means to be human. You don’t have cell-phones or a calendar, or a digital screen, and you start to shed layers. I’ve been on about 25 of these trips, and everybody changes by day three. Everyone is talking to each other, everyone looks better, their shoulders aren’t hunched. It’s a big part of my purpose in life, to bring people to these spaces to allow them to remember what it feels like to be human.

HMS: Do you think it’s better if people have had some experience of camping and rafting before going on this journey?

SS: No, you don’t need any experience, just a good attitude.