Honestly, I really thought that when I made one of my kid’s dreams come true, he’d point to something other than chocolate chip cookies as “the best part” of it. But that’s the joy of a 4-year-old—it all comes down to the sugar.
Toby has been DYING to fly on a plane for quite a while now. He would see me leave for work trips and ask when he could fly on a plane. I always said, ‘Someday!’ cheerily, which, oddly, wasn’t much consolation for a 4-year-old. So, when an old college friend of mine who lives in Seattle (and so we very rarely see each other) said she was coming to the East Coast with her daughter, I saw the perfect opportunity—spend some time with her and satisfy Toby’s plane craving. Little did I know that what he picked as “highlights” of the experience would totally surprise me!
So I snapped up two tickets on direct flights between Richmond to Boston and planned a whirlwind 48-hour journey. Toby, needless to say, was pretty darn thrilled. #understatement You should have seen him wrangling my wheeled carry-on bag (which probably outweighed him) to the car. He packed 10 books and a few tractors and he was set to go. #havetractorswilltravel
We got to the airport and parked. (He was also kind of blown away at his first parking garage experience. It’s the little things, apparently.) The elevator with the glass wall was also a big hit. We trundled through the airport and on the way to security, Toby stopped in his tracks. “MOM! That’s a racecar! In the building??!!!!” One of NASCAR driver Denny Hamlin’s old cars was parked by the escalators advertising the Richmond NASCAR race. Toby was pretty much blown away. “Take my photo by it, Mom!” Not the tourist attraction I anticipated, but I went with the flow. “That was so cool,” Toby muttered as we continued on. Consider the bar set high.

He was enthralled to see the planes taxiing around. I answered a lot of questions. We boarded and settled into our seats. He behaved like a little pro, dutifully fastening his seatbelt, little legs crossed in front of him when he wasn’t gluing his nose to the window looking out. Considering how screen-free his life is, he was pretty excited to see a personal TV screen right in front of him on the back of the seat.
Then, during the pre-flight announcements, they described the snack options they’d be handing out. “We have a choice between blue chips and chocolate chip cookies,” the flight attendant said, instantly filling my child with delight. He turned to me, eyes wide. “THEY SERVE COOKIES ON PLANES?” he asked with awe. So yes, take-off and the views were fun for him, but when the snack basket came down the aisle, his day was complete. He is his father’s child.
The only thing that might have eclipsed the cookies in his view was when we descended through the clouds, which filled him with joy. But then they served cookies again on the return flight, which did not include clouds. So, cookies won as what he’ll remember from his first flight. It just goes to prove, you can try and predict what makes a preschooler’s day and you will never, ever be right.
So here’s my version of the 48-hour trip, followed by Toby’s version. They vary slightly:
We landed, picked up our rental car, and navigated around downtown Boston to the USS Constitution. After a quick trip through the museum, we went on board and had a grand time checking out the cannons, hammocks and deck.

Chilly but cold! Then we drove to another Mt. Holyoke classmate’s house in a suburb of Boston, Toby met her two daughters, we had a lovely dinner, and I put him to bed.
Day 2, we woke up to Seattle friend and her daughter having arrived in the middle of the night, had breakfast and hit the road to visit Mt. Holyoke. Had a nice time walking around campus, had lunch there, and drove back. In the afternoon, we killed time a bit with a walk to a local playground, then went out to dinner and then it was bedtime again.
Day 3, we got up (thankfully this morning, Toby decided he could actually sleep past 5:30. Until 6:30 this time! In a household where no-one stirs until about 7:30. This is when our early morning routine at home backfires.) and hit a Panera to meet up with another MHC friend and her kids, then dropped Seattle friend and daughter at the train station and carried on to the airport.
Toby’s version:
We saw a NASCAR car inside a building!
The TSA guy told me he liked my haircut.
There were chocolate chip cookies on the plane. Seriously, COOKIES on the plane. Cookies, people.
We saw a big boat. It had lots of cannons. It was cold. They put 450 people on that boat, but all those people are dead now.
Mom’s friend’s kids have really good Lego sets.
The mountain was closed. (Toby was really looking forward to climbing Mt. Holyoke like we did last summer on our trip, but it was closed for the season.)
I got to eat ice cream TWO TIMES in one day. Once at lunch and once at dinner. Two times, people.
Slime is cool. I want some. (Slime/putty was a constant with all the older girls. Toby was intrigued, especially with the noise putty that farted. #boyalltheway)
I did the monkey bars!
I slid on my butt down the skateboard ramp. It was cool!
Mom’s friend gave me a super-cool book and a monster school bus toy! (Big hits, both.)
We got a flat tire on the way to the airport.
We flew home and there were cookies on the plane again and I watched a fishing show on the TV.
Seriously though, we had a fantastic time. Toby adored hanging out with my friends’ girls, who were 9, 10 and 11. He was, in a word, smitten. I will never forget the second morning, when they were reading books at the breakfast table and he went to get his Level 1 reading book about an egg and proceeded to very proudly read it aloud to the very unimpressed girls. He was trying so hard to impress them. Welcome to the world, kid. He also might need to hone his conversation skills, as apparently he thinks asking “What’s your name?” over and over again is scintillating dialogue. Again, definitely his father’s child.
So, #thetoby’s first flight is in the books. And I know now that if we book any more tickets, I’d better have some chocolate chip cookies handy to keep up the standards.

Wow, amazingly vivid description. Good job, Mom.
LikeLike
Chapter 1 of “Travels with Toby”: Done (to perfection).
LikeLike