An epic cross country for the Littlefield trio


The Littlefield Trio: Ben with his mother, Molly, and father, Keith.

There was a rather unusual and delightful trio of pilots at Antique Airfield this past Labor Day weekend for the Antique Airplane Association/Airpower Museum’s Invitational Fly-In at Blakesburg, Iowa.

They are the flying Littlefields — a mother, father, and son — from Crest Airpark near Seattle.

They’ve been back to Blakesburg many times, but this was the first year each flew an airplane there.

The Littlefields were camping with their airplanes tied down wingtip to wingtip in the “North 40,” and were as radiant as the morning sun when sharing their multi-faceted aviation stories.

“Our son Ben has a break between work and college right now, so we decided it was a great time to fly all three little airplanes — the Cessna 150, Cessna 140, and a 90-horse Super Cub — to Iowa. We flew 19 hours over three days,” explains father Keith.

“I’m the slow one in the Super Cub with 18 gallons of fuel, versus their 23 or 24 gallons, and I cruise 90 mph versus their 110 or 105 mph,” he continues. “So I flew the Cub as lead and I did the navigating just using charts. They both followed me and lollygagged around trying to slow flight behind me. Ben flew the Cessna 140, in which he got his private license, and my wife, Molly, flew the Cessna 150.”

Two-thirds of the Littlefield trio near Gillette, Wyoming.

The Littlefield’s affinity for aviation had its genesis decades ago. Keith’s father and Molly’s father flew in the military during World War II.

“My father was trained to fly in the ferry command and passed the love of flying on to me,” Keith says. “Molly’s father learned to fly in a Curtiss Robin in the late 1930s. He was an Army Air Corps flight instructor teaching cadets to fly the Stearman during the war. After the war, a Stearman became their farm airplane, and Molly soloed it as a teenager. She wanted to do commercial flying and few women were being hired then, but her father encouraged her to get her ratings and get ready because someday they were going to hire women.”

Molly and the Cessna 150

An aviation pioneer, Molly Flanagan was 24 in 1979 when she became the 23rd woman hired by United Airlines. She was the 22nd woman to upgrade to captain, and she will retire in July 2019 with slightly more than 40 years at the airline. She’s currently flying as captain on a Boeing 777, and continues to enjoy flying for fun in lightplanes.

Molly Flanagan Littlefield in her Cessna 150. (Photo by Roger Cain)

Describing the flight to Blakesburg, Molly says, “It was really a dream come true to spend three days just flying alongside of Ben in the 140 and Keith in the Cub! We had chats about flight planning and what route we should take, and who’s checking the weather and who’s got what survival gear.”

“We also figured out how we were going to land – who’s going in first and making radio calls for Keith,” she continues. “It was fun to see our love of flying be so deep in Ben, and see him making such great decisions. We were a very good team. We’d land for fuel stops and I’d usually get the credit card part of it started while one of them would ground the airplane and another would start fueling. Then we’d move airplanes and do it again, and again.”

She notes that the trio have ForeFlight on her phone and an iPad, but all three also have sectionals “that we keep handy just in case the electronic stuff stops working.”

“Paper doesn’t fail, unless it blows out the window,” she says with a laugh.

Molly Flanagan Littlefield with her Cessna 150E.

Molly flew her 1965 Cessna 150E, which her father, Tom, affectionately nicknamed Tin Lizzy.

N6290T has a sentimental history as it has been in the Flanagan family for decades.

“My sister Peggy and her fiancé Terry purchased this airplane together in 1978. They learned to fly in it, and were married in 1979. In 1980, she was eight months pregnant with her first son when she finally got around to taking her private pilot checkride,” Molly recalls. “The designated pilot examiner didn’t make her do full stalls because she couldn’t get the yoke all the way back.”

The youngest of Peggy’s three sons, Curt, also learned to fly in the 150. He’s now an Air Force C-130 pilot.

“When they decided to sell it three years ago, we bought it and did a little work on it,” she continues. “We painted some of the areas on the wings and ailerons that couldn’t be polished out, and matched the trim scheme with the 140. My sister’s delighted that I’m flying it, and I don’t know if it’s ever been this far east before, because it was a California airplane for so long.”

Keith and the Super Cub

Keith flew for 20 years as a military pilot flying Lockheed C-141s out of McChord Air Force Base in Tacoma, Washington.

“Then during my reservist years, I also worked for a commuter called Horizon Airlines for a short while and then I went on to Alaska Airlines. I retired from there 13 years ago, when I was just a child of 60,” he says with a laugh.

The couple met in 1993 at a Piper Cub fly-in in Lompoc, California. They married in late 1994, touring the Grand Canyon on their honeymoon in the Super Cub.

Keith found his 1949 PA-18 Super Cub in 1979 in Hardin, Montana, where it had been a duster and sprayer for 30 years.

Keith Littlefield with his 90-horse Piper PA-18 Super Cub.

“When I saw it, I noticed it didn’t have flaps, so I asked the FBO owner, Larry Romine, what kind of Cub it was. He said, ‘It’s a straight 90-horse Super Cub, serial number 4, and it’s for sale if you’re interested.’ And I thought, ‘Okay, that’s all I need to know, in one sentence!’”

He went back later and bought the plane, flying it home on a ferry permit.

“I took it apart and tried to restore it myself, but I didn’t have a shop, or the time, or the patience,” he says. “Finally I had other people help me over a period of 10 years, and we got it flying in 1989. It still has its original C-90 engine, fuselage, and wings.”

In addition to flying the Cub during their honeymoon, Keith has flown N5413H all around the country, ranging from the Golden Gate Bridge to the Statue of Liberty, and many destinations in between.

Ben and the Cessna 140

Ben, 22, has logged about 900 hours — almost all of it tailwheel time — and has earned his commercial, multi-engine and instrument ratings.

Ben Littlefield in the Cessna 140. (Photo by Roger Cain)

Quite naturally, Ben learned to fly from the best CFIs he knew: His mother and father.

“Molly did almost all of Ben’s primary instruction in the 140, and then as he got a little better in that, she was also teaching him in the family Stearman,” elaborates Keith. “I’d also been teaching Ben to fly the Cessna 185 and the Super Cub, so on his 16th birthday, he soloed the Stearman first, then the 185, then the 140, and then the Super Cub — all in one day!”

Ben Littlefield with his family’s Cessna 140E.

Ben flew the family’s 1946 Cessna 140, and describes the trio’s long cross country with a winning smile: “Oh it’s great flying together! It’s a lot of fun. Mom and I have radios so we can talk to each other and try to figure out what Dad’s doing. Of course, he knows what he’s doing, but sometimes we don’t know what he’s doing! So Mom will try to announce for him as best she can.”

“There’s nowhere else I’d rather be – it’s an absolute blast,” he adds. “I don’t know another family who has a mom, dad, and kid who fly a cross country together like this, and I think I’m very blessed.”

The Littlefield trio near Gillette, Wyoming. (Photo courtesy the Littlefield family)

Just like their other aerial steeds, N140F has its own longstanding family history. Molly and her brother, Dan, purchased the 140 back in 1981.

“Molly has flown it all over the country, and not long after we were married, her brother decided to sell his half interest to us,” Keith says. “Then we had the wings recovered, the trim painted, and a new interior installed. Soon afterward, we flew the Cub and the 140 all the way to the Piper Cub fly-in at Lock Haven, Pennsylvania, with 6-year-old Ben in one plane and his 4-year-old brother, Sam, in the other.”

“Funny thing was, Molly got one of those Best Classic awards there for the Cessna 140!” says Keith, adding with a smile, “So each of our airplanes are special to us in many ways, but the most special thing to us is that Ben can fly cross country with us like this!”

More Photos of the Littlefield Trio

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