My job as the founder/editor/publisher of “06880” has opened many doors.
Including the one on a Piper Cherokee 3-seater prop plane.
Last Saturday marked one of my most memorable mornings ever. I flew over Westport just after sunrise, enjoying a view of the beach, downtown and my home that is usually reserved for birds.
My pilot was Aiden Schachter — a rising senior at Staples High School.
He’s 17 years old. But Aiden is no ordinary kid.
After starting on a flight simulator in 7th grade, he advanced to lessons. On his 16th birthday in March 2022, he soloed.
He flew a plane before he drove a car.
Last month — after studying hard for the oral, written and check ride tests, and 5 hours in the air performing landings, takeoffs, maneuvers, emergency prep for landing at unplanned locations and more — he earned his pilot’s license.
Aiden Schachter, the day he got his pilot’s license.
That’s not Aiden’s only accomplishment. He’s built a thriving national business building and selling LED lightclouds. And he’s a varsity wrestler.
Keep your eye on Aiden. He’s going places.
One of those places was Sikorsky Airport. When I met him early Saturday morning, he was in his element. He bantered easily with men and women who have worked at the Bridgeport facility for decades, then went to work filling out paperwork for the flight.
He strode confidently to the small plane.
He performed his pre-flight checklist with utter seriousness. He explained everything about the plane to me in the manner of any experienced pilot (without the fake drawl).
He communicated with the air traffic controller. He revved the engine.
And off we flew!
We cruised at 3,500 feet, around 115 miles an hour.
The world looks different from that height.
Bridgeport’s Hartford HealthCare Amphitheater and Total Mortgage Arena are at the lower left.
Two things stand out: the amount of water. It’s everywhere: the Sound, rivers, tidal ponds, backyard pools.
Sherwood Mill Pond, with tiny Hummock Island (left center). At the bottom is Old Mill; the footbridge leads to Compo Cove (right). Above it: Sherwood Island State Park.
Compo Beach packs a lot into a (relatively) small space. Above it: Gray’s Creek, and the Longshore golf course.
Cockenoe Island. Saugatuck Shores is at left; Compo Beach is at the top, just below Owenoke and Gray’s Creek.
And the amount of greenery. It’s no wonder the power goes out so often. Trees are everywhere; at least a few of them are bound to fall.
The Longshore pools, marina and golf course are on the left; Gray’s Creek and Owenoke next to it, on the right.
It’s actually possible, from 3,500 feet, to see the border between Bridgeport and Fairfield, then Fairfield and Westport. The size of residential lots changes that dramatically.
Aiden gave me a full tour of our town.
There were fresh perspectives everywhere. One example: Downtown — which occupies such an outsized part of our mental picture of Westport, along with plenty of debate and economic power — takes up a tiny area of real estate.
The Ruth Steinkraus Cohen Bridge leads to downtown. The Giegerich office on Riverside Avenue is the large white building; the Levitt Pavilion is across the Saugatuck River, to the right.
Parker Harding Plaza (bottom); above it, Main Street, Bedford Square and Church Lane. The Post Road is on the right.
Winslow Park. That’s the Westport Country Playhouse and Playhouse Square (left); at the top left is the Gorham Island office building.
Saugatuck is another part of town that punches far above its weight, relative to its actual geographic size.
Saugatuck, looking west. The railroad station and I-95 are at left; the Cribari Bridge and then Saugatuck Rowing Club are to the right. In the distance are Norwalk’s Avalon apartments (formerly Norden).
Aiden says that Staples High School is the biggest building in town.
Staples High School is bordered by Paul Lane Field, Loeffler Field, Jinny Parker Field — and plenty of trees.
The Aquarion water tanks on North Avenue stand out in what seems from the air to be a forest. They’re a lot more conspicuous at ground level. (All photos/Dan Woog)
There are 17-year-old drivers I’d never get in a car with.
But flying with Aiden Schachter? My heart soars like an eagle.
Taking off …
… mid-flight …
… and landing. (In-flight photos/GoPro)
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I love when my flights go over Westport and I can spot my favorite places, but this flight looks amazing! Way to go Aiden!
Best 06880 post ever, especially knowing that Aiden stuck the happy landing. Thanks for photos, and congrats to you both!
Beautiful story. Amazing Aiden. Air Aiden ? It was not one of your very plain stories.
Thanks, Richard (I think). Re your last sentence: I guess you can find the cloud in every silver lining.
Yes. I am proud to find the cloud. Very nice story.
Actually, it was a plane story
Definitely one of the coolest columns in the annals of “06880”—and obviously Aidan is an exceptionally impressive 17-year-old.
I guess I didn’t realize that you could take up flying at such a young age; I was amazed to see that Aidan had “soloed” on his 16th birthday. (Geez, I didn’t even get my driver’s license until 4 1/2 months before my 17th birthday.)
So, a question for Aidan: how does he compare the degree of difficulty in learning the skills needed to fly vs driving (especially as he ended up learning how to fly before driving). Thanks.
Fantastic story and photos! Thank you!
And these are THE BEST drone photos of Westport to date.
What an extraordinary young man, and experience for you!!!
Great story – and great pictures!
Great pictures, nice pilot and the usual colorful explanatory Dan Woog prose!
I will share- I went up in a small top winged Piper in 1968 while in the USPHS and was really enjoyed the scenery over Atlanta!! Then the pilot and copilot decided to show me some aerial maneuvers- one was called a Chandelle- a tight 180 degree looping climb with accompanying quick crossover descent within a minimum turn radius. It was more like a crazy figure eight that went up and down too quickly for me- worse than a roller coaster. I did not make it through the entire loop before I lost my lunch! Needless to say I was never invited back for an encore performance- of the chandelle or my weak stomach!
I should have asked for Dan’s pilot- Aidan!!
Oops – that would have been about 55 years ago- 38 years before Aidan was born!
This is really cool, Dan. Young Aidan definitely seems to be going places. For him to be an accomplished pilot at such a young age is remarkable.
What a fabulous pilot and experience and photos! It’s so wonderful to zoom out, get perspective, feel free in the clouds and all with wonderful company! Thanks for sharing 🙂
It’s one way to beat 06880 traffic. I would like to go into business with Air Aidan Shuttle service. We will fly the high flyers
The only time I pay for a window seat is flying into HPN or HVN, on the side of the plane that I know will see Westport from.
Epic! Such awesome shots but a wild experience
Did Aiden’s flight instructor cut off his tie after his solo? That’s a proud aviation tradition. He will have fun with piloting a plane. It’s fun to take friends for birthday flights or even go on dates in an aircraft. In his spare time, he should consider being part of the Civil Air Patrol (https://www.gocivilairpatrol.com/), the civilian arm of the U.S. Air Force that helps in emergencies. A great way to stay engaged and active in flying and helping people without breaking the bank.
(response from proud Dad) Hah- Mark, he did indeed have his tie cut off — my parents purchased a tie for the occasion. It’s also a tradition to write the details of the flight on your shirt and cut it the section out as a keepsake. Additionally – He recently attended a few meetings of the Civil Air Patrol at Sirkorsky Airport and is in the process of becoming a member. He mentioned he wishes he did it a few years ago.
Great flight ! Reminds me of when young men & women gained their wings at Staples in Wilson Hopkin’s Aerospace course.
Dan Woog and Aiden Schacter what a beautiful chapter
Wonderful post and informative photo captions. Congratulations to Aiden for his accomplishment. The photos could be very useful to ground-based town planning; and perhaps a few flights during traffic hours to see the gridlock and its effects in real time would be helpful.
Dan, you forgot to point out the old McCoy homestead (the house has been leveled like many others) in the picture with the water towers on North Avenue. More than a few home runs were hit into North Avenue from there!