One Pilot's Adventurous Life

Sylvia Grandstaff has woven an interesting career.

Sylvia Grandstaff next to a CH-47F helicopter
Having chosen the CH-47F for its ruggedness and reliability, Sylvia Grandstaff logged over 900 combat hours during her two deployments to Afghanistan.Sam Weigel

One of the happy byproducts of a life largely spent flying, riding, sailing and exploring all over North America and beyond is that I have a great many friends scattered to every corner of the country and, indeed, the globe. Sometimes this means going years without seeing people, staying in contact by phone or social media, but it makes the eventual reunion that much more enjoyable. Meeting up with a beloved old friend after a long absence feels as comfortable as putting on a favorite pair of jeans rediscovered at the bottom of a drawer on the first chilly day of fall. That’s exactly how it feels tonight as Dawn and I reconnect with our dear friends Sylvia and Hugh Grandstaff after a three-year interlude.

We certainly could not have hoped for a much better evening for the occasion. We are sitting in Sylvia’s fragrant garden—overflowing with a wild profusion of luminous poppies, roses and herbs pollinated by Hugh’s own bees—as the day’s last light fades over the hills of northern Alabama and a nearly full moon peeks over the eastern tree line. Bullfrogs croak from a nearby swamp, Sylvia’s proud brood of laying hens cluck softly, and fireflies flit across the 3-acre homestead that Sylvia and Hugh fondly call “Cloudbase.”

It’s not much more than a grassy, tree-lined field set to the side of a turf airpark runway, but to Sylvia and Hugh, it offers the stability and tranquility that is missing from their busy careers and the dream of the airborne life they are building together. In a few years, they plan to erect a farmhouse here—and a hangar. For now, they reside in a handsome ­230-square-foot tiny home, practicing a functional minimalism that rather parallels how Dawn and I live aboard Windbird.

I’ve known Sylvia (nee Szafarczyk) for around 20 years, since she was an awkward, gangly teenage glider pilot and I was an equally awkward aviation nerd working through my professional ratings. We bonded over our mutual passion for aviation but became good friends because we have a very similar outlook on life and a pretty serious shared case of wanderlust. Our relationship was always platonic, but our closeness did cause some tension between Dawn and I when we first started dating. I was thrilled when Sylvia found her perfect counterpart in Hugh.

He’s basically a much cooler ­version of myself: alumnus of the United States Merchant Marine Academy who served as an officer on the space-age HSV-2 Swift, a keen sailor with ocean-racing experience, and an experienced pilot and instructor in ­everything from gliders to T-28 Trojans. Hugh’s great-grandfather was one of the first certified pilots in the United States—the family still has his first pilot’s license signed by Orville Wright—and Hugh grew up as a Southwest captain’s kid who ­managed and expanded the family scrapping business before succumbing to fate and becoming an airline pilot himself. As you can perhaps tell, I have a bit of a man crush on Hugh.

I can say, without a hint of ­hyperbole, that Sylvia is one of the smartest people I have ever met. She graduated in the top of her high school class and gained admission to a combined bachelor’s/­doctorate program at Rice University and Baylor College of Medicine. While at Rice, she got her degree in anthropology and volunteered for various causes—working as an emergency medical technician and doing medical internships in far-flung locales like Peru and South Africa. All the while, she was a pretty serious competitive glider pilot, flying regional and national competitions plus the Australian Junior Nationals (“Joey Glide”) and setting several national distance records. She met Hugh at an airport along the way; he bought Sylvia her first helicopter flight the day after she completed her first-year medical school exams at Baylor.

Shortly thereafter, Sylvia concluded that she didn’t really want to be a doctor and would never be happy in that ­profession. So she dropped out of Baylor to the almost universal horror of family, friends and professors. She had everything going for her, things she had worked for her entire life, and she threw it all away rather than continue down a path that was making her miserable. She didn’t really have a plan B other than the vague notion that she would do something in aviation. Quitting med school was one of the hardest things she’s ever done, and I’m impressed that she had the honesty and the guts to do it.

Sylvia was in a tough place for a bit—wandering and broke and wondering if she had done the right thing. She stayed afloat with part-time jobs flight instructing in gliders and wrenching on warbirds as a mechanic’s assistant. She reached out to one of her close aviation friends and mentors—a U.S. Army warrant officer and experimental test pilot—and soon followed his lead and joined the Army to fly helicopters, surprising many of us who knew her. Mind you, she was one of my more liberal friends, and this was at a time when helicopter crews were still absorbing heavy combat losses in Iraq and Afghanistan.

She earned first pick of aircraft in her flight school class and chose the CH-47F Chinook, telling me she was enamored with its reputation as a high-altitude workhorse. Since then, she has deployed to Afghanistan twice and accumulated more than 900 hours of combat flying as a pilot and instructor. I lived in a state of perpetual unease while Sylvia was in Afghanistan, my heart dropping every time the news announced another Chinook crash. Thankfully, she made it through unscathed.


Read More from Sam Weigel: Taking Wing


Before Sylvia’s second deployment, she applied for and was accepted to the U.S. Army’s Experimental Test Pilot program—a pretty huge deal for a Chief Warrant Officer of her age and experience, not to mention her lack of an ­engineering degree. She is, in fact, the Army’s first female warrant-officer test pilot. The Army sends their test-pilot candidates to attend the United States Naval Test Pilot School at Patuxent River Naval Air Station, where they go through the full 11-month test-pilot course along with Navy, Air Force, Marines and international-student counterparts.

The rotary-wing curriculum at Pax River is a notoriously tough program, but Sylvia excelled and graduated with Class 151. She also survived her narrowest scrape—worse than any she had been through in Afghanistan—when her UH-60 Black Hawk suffered a ­catastrophic engine failure at the absolute worst-possible moment during a single-engine test: other engine at idle, high airspeed and low altitude as called for by the test card she was flying. “If we each hadn’t responded immediately and done everything absolutely perfectly, we wouldn’t be here,” she says. Gladly, both pilots did, and the Army recognized her and her instructor pilot’s feat of airmanship with the rare U.S. Army Broken Wing Award.

Sylvia now works as an ­experimental test pilot, flying helicopters and airplanes for the U.S. Army Redstone Test Center in Huntsville, Alabama, which is how she and Hugh ended up buying Cloudbase. It is the fourth place they have moved their tiny home to in the past five years, in keeping with the itinerant nature of a service member’s life—and they’ll be spending a year in Arizona soon on a test-flying assignment.

Sylvia is flying gliders again, ­racing her beautiful and ultra-efficient Schempp-Hirth Discus-2a; she’ll be competing in the FAI Women’s World Gliding Championships in Australia next year. Sylvia also holds fixed-wing civilian ratings, including seaplanes and tailwheel endorsements, and she and Hugh have owned a Cessna 140 and a Grumman Yankee. They are ­currently airplaneless in Alabama, but aviation is so central to Sylvia and Hugh’s life—they were engaged at the Soaring Club of Houston and married in the old ­terminal at Houston Hobby Airport—that I’m quite certain this will change soon. They currently have their eyes on a particular L-19 Birddog, painted in an orange-and-white U.S. Army scheme.

Hugh, meanwhile, is about to upgrade to captain at his regional airline; I fully expect him to be joining me at the major airlines soon. Sylvia’s professional future is less certain. She deeply loves test-flying, but that aforementioned case of wanderlust and her desire to explore the greater world is often in conflict with “the needs of the service.”

Because this is Sylvia, I’m pretty confident that she’ll do what makes her happiest—and what gets her in the air most often, which for her is pretty much synonymous with happiness. Also, because this is Sylvia, there’s a good chance that whatever she does next is something that nobody else is expecting. Dawn and I look forward to future summer evenings at Cloudbase with Sylvia and Hugh, watching fireflies float across the airstrip and discussing the latest twists and turns of our friends’ wonderfully ­unconventional, inventive lives.