Rich Malagrifa stands atop Mount Katahdin, the highest mountain in the state of Miane, as part of his journey across the Appalachian Trail. | Photo: Courtesy of Rich Malagrifa


What would inspire Swampscott’s former chairman of the Board of Selectman and commercial airline pilot to trek more than 2,000 miles across the Appalachian Trail from Georgia to Maine? “Midlife crisis,” smiles Rich Malagrifa who chronicled his adventure and life milestones in his book “From 35,000 Feet to the Appalachian Trail, The Executive Hike of the Appalachian Trail.”

“I’m a very goal-oriented person,” notes Malagrifa, who was not an ardent hiker before he made the 7-month journey across 14 states.

The idea of hiking the iconic trail was sparked when David Miller’s “AWOL on the Appalachian Trail” kept popping up on Amazon on Malagrifa’s Kindle. He interpreted the frequent appearances of the guide as a sign from the universe that he should make hiking the Appalachian Trail his next goal.

A high achieving aviator, Malagrifa knew at an early age that he would soar to great heights and declared he wanted to be a pilot.As soon as the Lynn native met the age requirements, he obtained his pilot’s license. A passage from his book detailing his parents’ feelings about his dream to be a pilot illuminates his focused and fearless spirit.


“I had no desire to get a car like most teenagers,” he writes. “I just wanted my pilot’s license. I took my parents to the local airport to get their blessing. I was hoping for maybe some money and a ride to the airport when I started. This didn’t go over well. They felt a 16-year-old was too young to be flying airplanes. I didn’t agree. Things would be a little more difficult. I would have to wait until I was 16-and-a-half so I would have my driver’s license to drive myself to the airport.”

Soon Malagrifa was off to attend St. Louis University, where he obtained a bachelor’s degree in aerospace engineering in three years followed by Air Force pilot training at Sheppard Air Force Base in Wichita Falls, Texas and an assignment to fly A-10 Warthogs at England Air Force Base in Louisiana. After he left the Air Force in 1991, he was hired by a major airline.

His goal-oriented personality led him to hike the trail, however the rubric on the trail path was quite a departure from the footprint of his life as a pilot where parameters were defined. With no timetables or structure, Malagrifa had to discover a new way to navigate life. He did insist on shaving regularly and sleeping indoors, hence his trail mates called him the “Executive Traveler.”

He learned a couple of lessons along the way.

“You can’t judge a book by its cover,” says Malagrifa, referring to an affable traveler he met along the way named Bismark, who he later learned was a man named James Hammes who had left behind his daughter and wife and was accused of embezzling almost $9 million from Pepsi.

He also met Drag’n Fly, the 74-year-old woman who is the world’s oldest thru-hiker.

Another observation Malagrifa shared was the simple joys he witnessed people experiencing within their small towns. After he finished the hike, Malagrifa took a moment to do the same—to just enjoy sitting in his recliner in his Swampscott home. The rest, however, was short-lived. Although he wasn’t scheduled to work for a week, he elected to put in some overtime flying. A few months later he wrote his book. One can only imagine what’s next.

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