If longevity is the true test of a music festival, Pickin’ in the Pines has officially passed. In its 20 years, the gathering at Flagstaff’s Pepsi Amphitheater has blossomed into a nationally renowned event.

Set for Friday, Sept. 18, to Sunday. Sept. 20, the 2026 iteration features Grammy and IBMA winners, including The Infamous Stringdusters, Blue Highway, Kitchen Dwellers, Mountain Grass Unit, Bronwyn, Tony Trischka’s Earl Jam featuring Michael Daves, Woody Platt & the Bluegrass Gentlemen, Wood Box Heroes and East Nash Grass.

To mark the festival’s 20th anniversary, organizers have added a Thursday night performance by The Honey Buckets. The concert serves as an unofficial kickoff for early-arriving campers. Sunday’s schedule also runs later than usual, culminating in a celebratory set by The Infamous Stringdusters.

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The printed festival program will honor the milestone with commemorative spreads featuring attendee memories and photos.

In a nod to its roots, several artists who played the inaugural festival are returning, like Nolan McKelvey Band, Chris Brashear & Peter McLaughlin, and John Reischman & the Jaybirds.

Musicians aren’t the only ones coming back. More than 150 volunteers return annually, and the festival draws an estimated 3,500 guests daily. Some attendees have been coming since they were toddlers; now they’re adults who bring their families. That generational continuity is one of the staff’s favorite parts.

“We have so many returning attendees — people who make it part of their yearly plans,” said Teresa Wayne, an executive director.

“You could say it’s a community that’s been built around Pickin’ in the Pines.”  

Pickin’ in the Pines was founded by Flagstaff Friends of Traditional Music, a nonprofit dedicated to acoustic traditions. Currently, Pickin’ in the Pines has a small staff that also includes executive director Linda Mack and marketing director Lara Gomora.

Pickin’ in the Pines Bluegrass Festival goes beyond its genre’s moniker. The showcase celebrates other acoustic traditions like Celtic, gypsy jazz and Americana. 

The first year was small, scrappy and full of heart. Then the volunteer coordinator, Gomora was responsible for her roughly 100 supporters, many of whom camped on-site and worked multiple shifts simply because they loved the music.

Gomora said bluegrass endures because of its improvisation, instrumental breaks and the songwriting that swings between heartbreak and joy. 

“There’s a lot of tradition with it, like train songs,” Gomora said. “It brings a lot of joy to the audience.”  

The “experience” includes the Friday night square dance, a beloved festival tradition. Hundreds of attendees pack into the workshop stage area to follow the caller’s instructions, laugh through missed steps, and whirl through the night.

“It’s loose,” Wayne said. “Families can join and learn as they go. You shouldn’t feel intimidated or anything. It’s just fun.

“You don’t even have to have a partner, but people come in big groups, too. People are laughing and dancing. It’s after the last set on the main stage on Friday night.”

Pepsi Amphitheater, tucked among Fort Tuthill County Park’s ponderosa pines, is one of the festival’s secret weapons, as it’s shaded, grassy and spacious. The outdoor venue feels more like a mountain retreat than a concert site.

“The Pepsi Amphitheater’s been named one of the most beautiful outdoor venues in Arizona,” Wayne said. 

“It’s easy to attend, too. Some festivals are overcrowded, and you have to wait overnight to get in. There’s nothing like that here. It’s comfortable in the pines. There’s shade. There’s grass. There’s open seating.” 

Guests can sit in the amphitheater’s front seating or spread out on blankets across the lawn. 

Pickin’ in the Pines also nurtures the next generation of bluegrass musicians through its annual band contest, where up to 10 emerging bands compete for a coveted main stage slot the following year.

One standout success story: Crying Uncle, who won the contest in 2018 as teenagers. The band, who recently headlined a Musical Instrument Museum show, returned for a full set in 2019 and again in 2024, growing from prodigious kids into nationally recognized performers.

“It brings people together and creates a community of music lovers who listen to and dance to the music,” Wayne said. “Going to a bluegrass festival is always a really great experience.”