Interviewing Windham Hill Founder Will Ackerman

By Brendan Hedges, Michael’s brother

It was time to finally make the pilgrimage. 

Almost to the day of the 40th anniversary of the iconic, legendary recording sessions of Aerial Boundaries, we were heading to the tumbling, autumnal world where they took place (then, inside a comfortable country inn, with huge recording trucks parked outside): Windham County, Vermont. 

Mischa (driving in from New York City, where he was attending DocNYCPro, networking with an array of top documentary producers, editors, distributors) and I (driving in from Boston) met up in the red-bricked, blue-collar town of Brattleboro to grab lunch and check in our hotel before caravanning across the Connecticut River into the hamlet of West Dummerston – then up and around a switchback, earthen path to Imaginary Road Studios, home of Windham Hill founder Will Ackerman and his wife, Susan.

Will and Susan warmly greeted us, with open arms. We wanted to have an afternoon for us just to catch up on our lives, fill them in on our progress to date on the film – then grab the ‘B-roll’ we’ve been wanting since we wrote our script for “Oracle” – footage of Will walking through his spectacular woodlands at golden hour, amidst the muted, post-peak crush of fallen leaves underfoot. 

Not unlike actor Harrison Ford, Will is a talented, real-life carpenter – and built the beautiful structures on his property (home, guest house, recording studio, outbuildings!). It’s no surprise that Will’s exacting craftsmanship, the things built with his hands, was just as much a part of the rise of Windham Hill itself – an inspired aesthetic that brought together an extraordinary group of artists for nothing less than a new acoustic movement of their making. Not to mention the insane fidelity of the Windham Hill LPs, the Apple-like quality of their packaging design, and the instantly-familiar branding of the label.

When the mid-November last-light fluttered out, we decamped and all met up for burgers and beer in downtown Brattleboro (complete with a weekly trivia game going on), unexpectedly walking out later to a light snowfall. Mischa and I stayed at the vintage Latchis Hotel, which also houses a grand, Art Deco movie palace. The theater was done for the night when I poked my head in, but I got a quick tour from the manager. It’s always great to see a great big cinema with a huge screen and a balcony that hasn’t been carved up. Top Gun 2, or Taylor Swift.

The next morning, we arrived back at Imaginary Road with our terrific local crew, filmmakers Willow O’Feral and Brad Heck. Willow, a DocNYC ‘40-Under-40, happened to grow up with Mischa in Mendocino; her husband Brad is an equally gifted filmmaker, who also teaches at the University of Connecticut. We prepped the beautiful main studio as our primary interview spot, and went to work setting up for Will. We were surrounded by gold and platinum records, a visiting artist ‘signature’ door (with names like Pete Seeger, George Winston, Phil Aaberg), mementos and a Grammy Award – all creating the perfect vibe. Also on display was a framed photo of composer Erik Satie, a critical inspiration for Will from the beginning of it all.

We knew Will’s interview would be an essential one – so we had two primary sessions, one before and after lunch. We had him tell us the now-famous story of how he happened to see Michael playing at the New Varsity Theater in Palo Alto, after a determined Randy Lutge insisted he give a listen to the guitarist playing upstairs. We heard Will’s account of the ‘Aerial’ sessions, which were a major turning point in Michael’s career – with some unexpected twists and turns. Life on the road, the pitfalls of fame… no one but Will could take us down the long path of the Windham Hill part of this story, with such closeness, and insight – from the moment he signed Michael to a contract napkin, three Grammy nominations, all those memorable Evenings With and, finally, the tragic end of Michael’s life. It was a critical day for our film.

We packed up and said our farewells to Willow and Brad (who have a new film of their own in the works); Mischa was due in Philadelphia for an editing session, and, since I had the night free before heading back to Boston to catch my flight home, Will and Susan graciously treated me to dinner in Brattleboro, at Echo.

We talked about Satie, physicist Richard Feynman, Peter Tewksbury (my late mentor, who retired in Brattleboro with his wife), the upcoming documentary about Windham Hill, and our all-time favorite nonfiction reads (I just sent a promised copy of Wicked River, by the great essayist Lee Sandlin). I heard all about Liz Story’s recent concert at Carnegie Hall that Will and Susan attended, with Will introducing Liz and welcoming her back to live performances  after a long hiatus; I must have listened to Unaccountable Effect a million times. I’d just been to the opening of the ‘Acoustic America’ exhibit at the Musical Instrument Museum in Phoenix, and told them about seeing Michael’s black harp guitar, ‘Darth,’ on display. For a moment, I felt like the kid-brother again, back in the days when Michael asked me to tag along for part of a tour (the Texas leg of the Leo Kottke double-bill), or help run errands during the recording of Watching My Life Go By.

Memories, all around.

With such an important interview secured for the film, it was a perfect way to conclude our time together on this visit. Art, friends, music, food.

Just keep your hands off Will’s creme brulee.

MORE BEHIND-THE-SCENES PHOTOS FROM THIS SHOOT: