Conn documentary premieres Oct. 2 in Rapid City

Local climbing and caving legends Jan and Herb Conn are the subject of a feature-length documentary in the 17th annual Black Hills Film Festival at the Journey Museum in Rapid City Oct. 2 at 6:30 p.m., and tickets are going fast. 
The Conns are credited with establishing many classic climbs in areas like Carderock in Maryland, Seneca Rocks in West Virginia, Cannon Cliff in New Hampshire and the Black Hills. They also discovered and mapped over 60 miles of Jewel Cave. Along with their climbing and caving escapades, Jan’s musical play, “Run to Catch a Pine Cone,” has been performed throughout the country. 
The documentary, “Catching Pine Cones,” started as an idea in 2010 and became a reality in 2025 through the efforts of the producer and director, Chad Heddleston, and the editor and cinematographer, Parker Michels-Boyce, both of whom will attend the Black Hills Film Festival and answer questions about the documentary. 
“I first learned about the Conns and their epic climbing career in the early 2000s because I was finding that I was repeating a lot of the routes that they had done in like the ’40s,” said Heddleston. 
Heddleston had worked on other rock climbing films previously and was intrigued by the Conns and the notable impact they had in the climbing world close to where he lives in Virginia. 
“I did a deep dive on Wikipedia with all the climbing stuff that I could find, and the story just became more and more interesting to the point where I was very disappointed when I learned that Herb Conn passed in 2012 and that there wasn’t some sort of a film or somebody giving a comprehensive look at their story,” said Heddleston. 
From there, he reached out to friends of Jan’s and became a friend himself, staying at her home and talking with her for a couple of days in December of 2015. 
“That was when we got the only video that we’re aware of that has ever been taken in their tiny home, which is an off-grid home and a very small, special place that not a lot of people went into,” said Heddleston. 
“I knew it was going to be very challenging to do a decent job of telling their story until Parker came on with his professional expertise,” said Heddleston. 
Also residing in Virginia, Michels-Boyce has a background in photojournalism, having done some short documentary videos over the years. However, this was his first feature-length documentary.
“When Chad approached me in 2020 and started telling me about the Conns, pretty immediately I realized that this was one of those stories that you only get once every so often, and it was definitely worth pursuing and telling and really doing it right, because it’s also a piece of history,” said Michels-Boyce.
Heddleston said the Conns’ story is pure American history, but also a really interesting life story that anyone can enjoy learning about. This was enhanced in the film because Jan was “such an amazing storyteller and such a great character with so much spirit that she made it easy. She made the film better just by being who she was,” said Michels-Boyce.
As incredible as the Conns’ sustainable, off-grid life of climbing and caving was, Heddleston said what stood out to him was the way the Conns did everything as a team. 
“I call it a dirt bag fairytale, because climbers refer to dirt bags as it’s kind of an admirable lifestyle, and they were like the first. They were the dirt bag fairytale. Only it was true,” said Heddleston. 
“I think the more that I learned about Jan and Herb and started to see their creativity, their sense of humor and just the way that they approached everything that they did, I was so happy to be able to help tell the story in a way that might inspire other people to live that way or to consider alternative ways to live,” said Michels-Boyce. “In a way, they set such a quiet precedent of what’s possible.”
To make the documentary true to the Conns’ nature, Heddleston and Michels-Boyce knew they needed to include their sense of humor. 
“This film couldn’t just be a straightforward, linear documentary. It needed to have the same spirit and sense of fun that the Conns lived with,” said Michels-Boyce.
“But also they were legends in rock climbing and caving, and you couldn’t tell this story without showing that they were truly legendary,” said Heddleston. 
Using the abundance of archival material available, Heddleston collected bits and pieces for the documentary, including a clip from the earliest climbing video in the country to his knowledge from the 1940s in the D.C. area. 
“There was also footage from the ’50s, from the ’60s. There were many things that we uncovered later. It was the ’70s, ’80s, ’90s, right up through today that we were able to include. So, just from a historical standpoint and the preservation that we were trying to do, we knew this story would be easy to tell, but to tell it in their voice, we knew would be more of a challenge. And it could only be fun and appropriate if it was kind of heard through their voice,” said Heddleston. 
To capture this, Jan Conn shared the story and her music with the film before her passing in 2023. This included a three-hour interview completed in 2021. 
Since the Conns were very modest about their accomplishments, the documentary also includes interviews with friends, family members and the next generation of climbers and cavers, putting everything into perspective. This required several trips, including many to Custer. 
“So much of this involves climbing or caving in places where you really got to get out there and take a little time. So these are not just quick interview trips. These are climbing, exploration, adventure journeys that we were diving into and also interviewing many different people to get all the different angles and make sure we weren’t missing the best way to tell the story,” said Heddleston. 
Every time they got on the ground in Custer, Michels-Boyce said they ended up meeting people and seeing things that they had never expected, which was a huge part of putting the film together. 
“We probably produced around 120-130 hours of our own footage, coupled with probably eight or 10 hours of archival video and then thousands of photos,” said Michels-Boyce. “We found a lot of copies of old articles and letters that they had written back and forth to peers in the climbing community. So once we started putting all that together, it was actually tough to figure out what to pick and choose because we found that we couldn’t include everything that we wanted.”
Based on Jan’s musical play, the documentary was titled “Catching Pine Cones” with the idea that catching something mid-air, between heaven and earth, is a special moment. 
“Pine cones fall all the time, but who actually takes the time to try and catch one? It’s a difficult thing, but it’s kind of fun,” said Michels-Boyce. 
Editing began in 2023, and the first cut was over two hours. It was eventually cut down to the one hour and 13 minutes film it is today. “Catching Pine Cones” premiered at its first film festival in October  2025 and has since been viewed at film festivals across the United States and in several countries across Europe. 
“I’ve watched it probably 100 times, and I still enjoy it. I think it’s a great look at a life well-lived, and every time I watch it, I find myself reflecting on my own life and how I want my legacy to look,” said Michels-Boyce.
“In the case of the Conns, I knew that no matter what would happen with the story, it was worth trying to capture the story and trying to put it together,” said Heddleston. “To have it succeed in such incredible ways has just been unbelievably rewarding. It’s such an honor to be able to tell their story.”
Because the story of the Conns was tied to the Black Hills, Heddleston and Michels-Boyce knew they needed to apply for a slot in the Black Hills Film Festival, and they received word that the film had been chosen to be part of the festival in August. This will be the South Dakota premiere of the documentary. 
In anticipation of the festival, it was announced Sept. 15 that “Catching Pine Cones” will receive The Best REEL South Dakota Film Award. 
“We’re very excited to get the REEL South Dakota Film Award,” said Heddleston. “We’re hoping that a streaming platform would be interested in helping us distribute ‘Catching Pine Cones,’ but for right now, our distribution will be through public media through Virginia Public Media and American Public Television.”
More information can be found at catching
pinecones.com and black
hillsfilm festival.org.