Celebrating 10 Years Of WinterWonderGrass With Oliver Wood, Dave Simonett & More

WinterWonderGrass Colorado celebrates 10 years with the ninth installment of the festival in 2022. While the annual event featuring the intersection of music, winter sports and more, had to pause for the COVID-19 pandemic, WWG returns to Steamboat Springs, Colorado February 25 – 27 with a lineup including headliners Trampled by Turtles, The Wood Brothers, and more.

JamBase recently had a chance to chat with Trampled By Turtles’ Dave Simonett and The Wood Brothers’ Oliver Wood to discuss their involvement in the festival over the years, along with some of their most memorable moments. As WWG Colorado celebrates a decade, JB also spoke with WinterWonderGrass founder Scotty Stoughton to talk about the festival’s origins and expansion, as well as perseverance through the pandemic and more.

Hailing from Duluth, Minnesota, Trampled By Turtles and Dave Simonett are no strangers to winter weather. In fact, Dave has a side project called Dead Man Winter. “Being from Minnesota, there’s a good amount of winter references in a lot of our songs,” Simonett said.

In other words, TBT knows winter. For Dave, it’s WWG’s celebration of winter — and all that comes with it — that resonates.

“The festival itself, I think it’s such a cool idea to get people out,” Simonett said. “Maybe I’m sheltered or something, but for me, I never think of having an outdoor festival in February in the mountains. But they do it, and people come out and have a great time. I think it really speaks to the quality of the event, the location. It’s kind of a big celebration of winter, which I think is really great.

“We’ve been in touch with the WinterWonderGrass people for a really long time and it’s been great. They’ve been great supporters of us and we always love to go out and do it. You know, it took me a couple years to get used to playing a stringed instrument in like five degrees [laughs]. That could be kind of be an acquired taste. But honestly, they do a really good job of somehow heating the stage to a point where it’s possible to do it. And everybody just kind of has fun with it too.”

Fun and five degrees may not jive for many. But there was one experience Dave had at WWG in Steamboat Springs when TBT last headlined the festival in 2019 where the band and the audience made the best out of a chilly situation.

“The last time we played was really memorable for me because it was about five degrees. We got up and it was that cold. And then right when we started playing it just dumped snow. I could barely see the end of my guitar. It was like a whitewash blizzard.

“The crowd was awesome. Everybody was having a great time. It was almost like in the summertime at a festival, if it rains and everybody starts diving in the mud. It was great. It was really one of the more memorable sets of music for [me] performing-wise.”

A common thread that seems to run through the WWG experience for musicians is the awe that such a festival could even happen in the first place, which is quickly replaced by a sense of wonder when the artists see how much fun the audience is having. The energy of the audience always enhances the music, a sentiment The Wood Brothers’ Oliver Wood shared.

“It’s a real unusual festival, obviously because it’s outside of a ski area in the middle of winter,” Wood said. “And I remember both times feeling like, what the heck are we doing? You know, being cold and snow falling on my ancient guitar, on my brother’s ancient bass, and thinking ‘[this is] not really logical.’ But at the same time, we had such a good time. And the fans were having a great time. So it’s this weird clash of your brain where you’re just like, ‘what the heck are we doing’ and ‘whoa, we’re doing it and it’s fun.’ I like stuff like that.

“Sometimes when you do shows in the Dominican Republic or in Miami Beach it’s the opposite. You’re like, ‘what are we doing? It’s hot and wet and it doesn’t make sense. But check it out, everybody’s having such a good time.’ So I have very fond memories. I remember looking back at a video on YouTube and [thinking] ‘look how cold we looked. But we sound pretty good.’ Sometimes struggle makes good art.”

As Dave and Oliver both expressed, the weather at WinterWonderGrass keeps things interesting and so does the audience. Wood recalled a memorable moment in 2015 when he and his brother, bassist Chris Wood, and multi-instrumentalist Jano Rix experienced a first at WWG when it was still held where it all began, in Colorado’s Vail Valley.

“I do have an experience that sticks out in my mind. At the first one that we did, which I think was in ‘15. We had a stage diver. You know, we’re not like the most thrashing band in the world, but people were getting into it. We have a song called Luckiest Man,’ which is not even a rocking song at all. We have some pretty rockin’ stuff but that’s more like a ballad, it’s like a singalong.

“I remember this guy jumped up, got through security, jumped over the railing at the front and got on the stage. And before the security guys could grab him, he dove off the stage. That had never happened; that’s not something you’d expect at a Wood Brothers show. So that really stands out. But it was a very peaceful experience and nobody got hurt.”

While The Wood Brothers had their first appearance (and first stage diver) at WWG Colorado in 2015, Oliver and Chris are no strangers to the Rocky Mountains having grown up in Boulder.

“As kids, we would go on ski trips a lot,” Oliver said. “So we’ve skied all those places up there and I have super fond memories of that for sure.”

Skiing and winter sports as well as the camaraderie that comes with them is what sparked the mind of WinterWonderGrass founder Scotty Stoughton, as he explained:

“I’m from the East Coast and I grew up skiing in Vermont,” Stoughton said. “One thing that I never forgot were those really amazing moments that we would share after being on the mountain, no matter what the conditions were like. I just remember going down to the base lodge and there’d be a fire going outside, there’d be some people playing music, doing some pickin’, there’d be some barbecuing. I never really lost that sense of how beautiful that simple time was. It’s where everybody got together as a community and shared stories of their day and had a beer. The kids were playing freely, the fires were goin’, the music was goin’ and the beer was flowin’. I’m like, ‘this is epic.’”

To capture that après-ski feel Stoughton speaks of, the inaugural WinterWonderGrass took place in 2013 in a parking lot near the Beaver Creek Resort in Edwards, Colorado boasting a lineup including The Infamous Stringdusters, Greensky Bluegrass and more. But even as the festival has expanded to include events in California’s Lake Tahoe region and Stoughton’s native Vermont as well as the Colorado iteration moving from the Vail Valley to Steamboat Springs, Scotty has remained steadfast in preserving WWG’s intimate and local feel wherever it may be.

“Even though it’s grown, it’s always grown with the intention of quality over quantity. It’s never how many more people can we get? How many tickets can we sell? Where else can we expand? It’s never been about that for me. It’s never been about the money, because it’s not in the music business obviously. It’s a terrible risk and it’s a horrible thing to get involved with unless you absolutely love it. But I absolutely love it.

“You know, I created this thing, I put my house up for equity because I didn’t want any partners. I didn’t want to partner with a major promoter. I didn’t want any strings attached. I didn’t want to have Bud Light blow-up bottles on the sides of the stages and everything branded. I wanted local food, no Red Bull, no Coke, no Pepsi, organic when possible, really put thought into the whole experience.”

While Scotty’s vision was not without challenges, he and his team mitigated them by putting in work connecting with the community and its leaders, seeking sponsorship and participation from local artisans and businesses as well as really listening to what the community wanted.

“The greatest thing that we do is, I like to go in and meet with the community,” Stoughton continued. “Throw town halls and have gatherings and just speak and be available. So I can really gauge what the community wants. And so, because I do that, I think the challenges are kind of avoided.”

One challenge that could not be avoided, however, was a global pandemic. Although WinterWonderGrass Colorado took place in February 2020 just before COVID-19 shut the world down, the upcoming WinterWonderGrass California had to be put on hold that year as were all iterations in early 2021.

In the intense and isolating early stages of the pandemic, Stoughton and the WWG team were quick to provide archival festival videos to home-bound fans through WinterWonderGrass TV. In 2021, WWG pivoted to RiverWonderGrass, an intimate boat trip on the Colorado River featuring music from WinterWondGrass Colorado favorites like flat-picking champ Tyler Grant, Leftover Salmon banjoist Andy Thorn, members of The Infamous Stringdusters and more.

Perhaps just as at home on the water as on the mountain, Scotty — who was one of the first people to paddleboard the entire Grand Canyon — captained RiverWonderGrass. The musical river adventures provided much-needed healing and camaraderie for pandemic and politics-weary participants, musicians and attendees alike.

“I went out and led all these trips and I got to talk with the fans, 20 fans, people that I’ve never met, that have known me for years, that have been supporting WinterWonderGrass for years. And I got to sit one-on-one with music playing, drinking coffee, going deep in conversation. And I’m like, ‘this is the most important thing.’

“That’s what’s gotten me through. Now we’ve got RiverWonderGrass and WinterWonderGrass. We’re really not trying to change the world, we’re just trying to let the world know, let the people know, that they are supported and there are a lot of great things happening right now.”

One of those great things is WinterWonderGrass Colorado 2022 in Steamboat Springs. When JamBase asked Stoughton the same question we asked Dave Simonett and Oliver Wood — What are some of your most memorable WinterWonderGrass moments? — it was more a performer, and one of Oliver and Dave’s fellow headliners, that stuck out in Scotty’s mind.

“Certainly watching Billy Strings rise up from a guy who — we gave him a shot years and years ago — showed up in a van and played at first on the side stage. And then the next year we gave him a shot, the next year gave him a shot, put him on the main stage the next year, then put him higher up on the main stage. Then in 2020, the last WinterWonderGrass, was the first headlining set of his career.

“When things are aligning and we have an opportunity to support rising stars, Billy obviously being the biggest, it means a ton. And the fact that [Billy Strings] chose us to do their Renewal Festival, it’s how it should be. They completely honored the people that got them there. Nobody does that. Everybody gets big, they go with the majors and you’re kind of shut out.

“So I was sitting backstage with Billy in October and I was like, ‘Hey man, thanks for having me back here. I appreciate your hospitality and I’m so proud of you’ and he’s like, ‘You’re family, you’re welcome back here. Thank you for treating me the same as all the other big bands when I was in the back of the van. Thanks for putting me on the main stage. Thanks for giving me headline spots. I’ll never forget it.’ So those moments are pretty cool.”

Catch Trampled By Turtles, The Wood Brothers, Lukas Nelson & Promise of The Real and many more at WinterWonderGrass Colorado 2022 February 25 – 27 in Steamboat Springs. Head here for ticket info.