Over the past ten years, WinterWonderGrass founder Scotty Stoughton has become a leader among music festival promoters. When he answered the phone to discuss WinterWonderGrass with Live For Live Music, he was in the middle of sorting through a mountain of paperwork for the event’s latest expansion, BajaWonderGrass, set to debut in Mexico in April. Since creating WinterWonderGrass in 2013, he has grown the enterprise from a small winter festival in Colorado to a national—and now soon to be international—community with a variety of events in different locations throughout the year.

“I’m never one to set a plan and say, ‘This is how we’re gonna conquer the world,’ or, ‘Let’s create this festival and this brand’—I don’t even like the word ‘brand’—’and then let’s grow it and build it and sell it.’ A lot of people do that with festivals and other things. That really wasn’t the intention [with WinterWonderGrass]. It was to create something that just felt good, and that was right—right for the community, and right for the bands, and right for me, and right for the world. I mean, it really is that simple. That was the intention.”

Stoughton entered the music industry as a musician, which he says gave him insight into the sacrifices artists make to turn their dreams into reality. “The main thing I took from that experience that influenced and inspired WinterWonderGrass was the amount of dedication that these artists put into their career. It’s super fun in your twenties, right? It’s a traveling party. But there are those that go on to a path of success, and they learn that a greater degree of commitment has to come with it, and also dedication to craft.”

He hosted his first shows in the late ’90s while managing State Bridge, a beloved Colorado venue at which he temporarily resided in a teepee while bartending and learning to produce events. “It was a remote location off the grid on the Colorado River. It was surrounded by teepees and cabins and railroads, and all these hippies and bikers and yuppies and farmers and river rats, every kind of person would come out there on the weekends and just get down. And it really kind of had an indelible impression on me where I saw the power of music to build community.”

The desire to foster community stayed with Stoughton as he assisted teams with larger events in L.A. featuring some of the biggest names in music, from Snoop Dogg and Diplo to The Head and the Heart and Nathaniel Rateliff. “Eventually, I realized I was much better at producing events than playing them, and my calling was to be the person that can hold space for people to shine and thrive instead of being that person,” he said. “I’m better at being an organizer behind the scenes, and I love setting the table for individuals to have the best experience of their life.”

Wanting to create a more wholesome, “community-centric and kid-friendly” festival, he found his niche in Colorado’s burgeoning jamgrass scene, hosting some of the region’s top acts at the inaugural WinterWonderGrass in Vail Valley in 2013, though he said “it wasn’t just string music or bluegrass. I booked bands that sound good if the lights go out. If the power goes out, and you can jam and hold the crowd and entertain us and entertain yourself and take it with a light heart, then that’s who I’m going after.”

Some of the acts on the bills for the first few editions of WinterWonderGrass included The Infamous Stringdusters, Greensky Bluegrass, Leftover Salmon, and Billy Strings, who, after working his way up the bill, played one of his first headlining sets at the festival in 2020, later returning in 2022 the day before his appearance at the Grammys.

Billy Strings  – “Highway Hypnosis” – WinterWonderGrass Steamboat – 2/21/20

In 2014, the year after its inaugural run, WinterWonderGrass expanded to Tahoe, CA, which remains the festival’s second home, and after outgrowing its second location in Vail, the flagship WinterWonderGrass settled in Steamboat Springs—as did Stoughton himself, which would establish a pattern for the promoter. Rather than picking locations based on market research or other economic factors, he chose communities that he himself felt deeply rooted in, or at least substantially connected to. That is obvious in his recent decision to host a small festival in Baja, where he built a house for his family, but it is also evident in his approach to expansion throughout the years.

Before launching WinterWonderGrass Tahoe, Stoughton said he “dabbled in the community,” hosting open houses to ensure that the locals were on board with his ideas every step of the way. “I was like, ‘Hey, this is what we’re thinking. I love your community. I’m certainly super mindful on the environmental impacts of gathering people and bringing people into a pristine environment.’ And after those conversations, people were very supportive and totally into it. And they really trusted our environmental ethos.”

Stoughton’s commitment to sustainability, in addition to ingratiating him with the locals, has helped position WinterWonderGrass as an environmentally conscious leader in the live music industry. As the festival has continued to expand, he has set the goal not only to minimize the event’s negative environmental impact, but to actually have a positive impact on the local communities. “We spent a ton of money on making sure this is not green- or whitewashed. It’s more like, let’s really do it. Let’s do it better than the community was doing it before we got here. And that’s been a really important part of our growth and our evolution.”

Environmental sustainability, though, is just one of the ways WinterWonderGrass strives to lead the industry. “We want to be leaders in terms of creating kids’ experiences, in terms of integrating nonprofits, in terms of being as green as possible, recycling, composting, upcycling, finding local vendors,” Stoughton said, and he and his team have made fruitful innovations in all of these areas. That includes his wife, who he said “goes around and hunts down small businesses around the country, especially female-owned small businesses, looking to find folks that have had a little more of a hurdle and give them an opportunity to work with us.”

That ethos has spawned other WinterWonderGrass events, including festivals in Vermont and a charity event called Campout For The Cause, and during the pandemic, he blazed yet another trail with the launch of RiverWonderGrass, which offers fans the chance to enjoy a river rafting adventure with their favorite artists, who perform throughout the trip.

“We take artists on these four-day river excursions through remote desert canyons—20 guests, four artists, and ten guides—and the tag is, ‘It’s more purpose than party.’ Of course, you can come out there and have some beers at sunset, but it’s more about, how do we really reconnect with each other and ourselves and nature and the water and mountains and trees. It really is invigorating, and it’s been an amazing expansion because now I get to talk to people that come to my festivals and meet them and get one-on-one time. And just imagine getting up in the morning with Lindsay Lou singing to you, and the artists having coffee by the fire and catching up with people who have been supporting their career, catching up on their stories. That’s the stuff I like to do. And that’s what’s important to me in our company.”

Stoughton says his only regret looking back on ten years of WinterWonderGrass is letting people down when events like Campout For The Cause or WinterWonderGrass Vermont have to take years off, but he says he’s learned that constant growth can be a recipe for disaster, so sometimes contracting is the best way to expand.

With this year’s WinterWonderGrass Colorado in the books, Tahoe coming up this weekend [get tickets], and Baja on the horizon, WinterWonderGrass is alive and well at ten, and Scotty Stoughton is still pushing the boundaries of what a festival and festival promoter can do. Leading the way for a music festival empire that would be easily marketable to a larger, corporate event production company, one idea still guides every decision Scotty makes: community.

For more information about WinterWonderGrass’s various events, head here.