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I was randomly thinking about this very important question today, and I'm interested to see what you guys think. Here are my thoughts:

- Eugene definitely drives a Prius.
- The Parkers have a Honda Odyssey.
- Whit has a Buick of some sort (probably old).
- For some reason, I see Wooton with a PT Cruiser. Does that sound accurate?
- Jason definitely drives something super sporty, but it also has to be practical, so I'm a little stuck on that one.

Anybody else have thoughts?

This is a topic I can get behind. Connie 100% drives a volkswagen beetle.

We do know a little bit about Odyssey characters' vehicle choices, although not much. A few that come to mind:

Bernard had at least three known trucks, his old one ("that had never [yet] let him down", until the road trip, when it required repairs or modifications three separate times), the one he bought at the end of the road trip to California, which eventually developed some 'quirks', and the new one that replaced it in "Two Friends and a Truck".
Tom had a farm truck that he used to deliver shipments. It was old and possibly had some other distinguishing feature, as Jessie recognized it down the street in "All's Well With Boswell".
For a time Eugene didn't have a car, even after getting a license, preferring to cycle around or get rides as needed, but he did get at least two, and possibly more eventually: one that was stolen and used as a getaway car, a car which broke down during a trip to visit Katrina's family (possibly the same one), and the car that replaced that one.
Connie wanted and was given a red Prelude* to replace her old car (possibly the 'brand new used' one that she was saving up for years before in Suspicious Minds).
The Mulligans didn't have a van (much less a bus), which resulted in at least one of their vehicles being regularly overstuffed during trips to school.

* Eugene calls it simply a "Prelude", but Connie says more when she mentions the car model's name. Unfortunately, I can't make out any of it after "Prelude". I wouldn't be surprised if Katie Leigh ad-libbed gibberish.

As far as conjecture, Whit does strike me as the kind of person who would buy a modest, reliable, good-quality car (possibly in the '60s or '70s), then drive it ever after.
I don't know what Wooton would have, but I expect it to be strange, maybe stranger than a PT Cruiser, or even a VW Bug. Maybe a Nissan Cube.
When he was younger, e.g. "Darkness Before Dawn", I see Jason with something like a Camaro or a Firebird, but now that he really has settled down, I think he'd be more practical and less flashy; maybe a Ford truck, or even some sort of Jeep.

MonkeyDude wrote:Connie 100% drives a volkswagen beetle.

I can see that. And it's definitely that minty lime greenish color.

Bob wrote:Bernard had at least three known trucks, his old one ("that had never [yet] let him down", until the road trip, when it required repairs or modifications three separate times), the one he bought at the end of the road trip to California, which eventually developed some 'quirks', and the new one that replaced it in "Two Friends and a Truck".

This is for sure a Ford Ranger.

Bob wrote:Tom had a farm truck that he used to deliver shipments. It was old and possibly had some other distinguishing feature, as Jessie recognized it down the street in "All's Well With Boswell".

And good old all-American Tom drives a Chevy Silverado.

I can also see Jason with a souped up Honda Civic.

No, no, no. Tom is a good ol' boy who operates a farm and apple orchard in rural Ohio. The show begins in 1987, and most older people in rural areas drive vehicles for approximately twenty years, or until they wear out. Since Adventures in Odyssey begins in the late 1980s, we can make the assumption that Tom is using a truck around the farm that is at least thirty years old, as American vehicles in the first two decades of the postwar era were built to last a lifetime. His truck most likely looks something like this:

I stand corrected. You are quite right.

Harlow rides a moped and Penny has a station wagon. one of Eugene's cars must have been a 2-door because in 'Tom for mayor' when he and Sam lock the doors they only lock theirs and the two guys start banging on the window, instead of using another door. although in 'the perfect witness' his car is a 4-door as Jenny doesn't have to climb over the front seat to get out at the police station. I'v also been wondering if Eugene shares a car with Katrina, but I think they may have one each, as Eugene picked up Buck once and not long after they got home we hear Katrina arrive and Eugene calls out to her when he hears her put down car keys.

I always imagined Tom driving something like a small 40's or 50's 1/2 ton pickup (similar to the one on the newer cover of 'wish you were here'). it's design means would be pretty easy for Jessi to spot and she could have hidden where Tom wouldn't know she was there unless he heard her. Tom is also quickly able to turn around in 'the Nemesis', so it must have been about the same size as a car. He would also be able to fit it between trees in the orchard to load crates of apples easier.

I don't think the writers think about it that deeply.

Well, probably not, but if these things can be inferred or determined through analysis, I don't see that there's a reason not to do so.

I'm sure the sound designers think about it more than the writers at least. =P

According to the Wiki, Eugene's first or second car was a Saturn.

The chairman has a helicopter.

In the episodes, there are quite a few characters who have said what cars they drive.

In “Much Ado About Jealousy”, Jillian drives a red hatchback which she confuses with someone else’s and gets in covered in mud.
In “Mean Streak”, Penny mentions Connie drives a hatchback as well.
In “A Penny Saved”, Wooton says that Penny drives “a blue 1981 Datsun 210 hatchback”, which she lives in for several days. (Wow, a lot of people drive hatchbacks)
There are several episodes (“The Toy”, “Auto Response”, etc.) where Detective Don Polehaus drives a police car.

As far as characters who have not specified in episodes what cars they drive, we can only speculate:

I imagine that Regis Blackgaard drove a limousine or something expensive.
Bart Rathbone probably drives some cheap junky car.
I don’t know why, but I imagine that Mrs. Kramer drives a really old car. A car that looks something like this:

I remember one Podcast episode that talked about how the sound designers got sound effects for Mr. Skint's truck in the Green Ring. I imagine that it's an old, noisy diesel that has a lot of mechanical issues because Skint has used it for many years. For some reason, I imagine that it's so loud that you could hear it coming a mile away.

In The Long End, Two-Bits steals a truck from a parking lot, and Skint implies that it is a newer model (compared to his old one, I assume). I guess they used both trucks in The Long End since Mr. Skint and Buck were in one car and Two-Bits in another.

Well, there's what they would drive, what they'd wish to drive, and what they're confirmed to drive.

I'm mostly going for the first with my list.

There's also the timeless yet dated nature of AiO. We haven't seen a lot of the characters since around 2008 in our time. This makes me personally think about older rigs. I live in a poor rural area, so plenty of 90s/2000s cars+SUVs and 70s-90s pickups are still pretty common. That influences my headcanon of what characters drive too.

I imagine Wooton would probably drive something like a Nissan S-Cargo (look it up) or maybe a Fiat Multipla.

I think Jason would drive a newer Crown Vic or a similar poor man's sleeper. Low-key and a bit older, with some good horsepower.

Ted Humphries would be a classic 50s or 60s car guy.

For Connie, I think she'd want a modern Mini, but she'd regret it if she got one. Very cute and sorta peppy, but unreliable. Kinda seems perfect for Connie.

Mrs Kramer would drive a 2000s Cadilliac or Lexus. Maybe a Toyota Avalon.

Captian Quidd would have an Amphicar-like vehicle with a "rebuilt" engine, fake wood paneling, and rotting foam seats. With rusty wheels, and sunlight-cracked, studded snow tires, but without working brake lights. Unrealistic vehicle? Yes, but very Captain Quidd.

Edwin would have Shakespeare drive him around in a big Cadillac SUV that he can't even begin to pay off.

Bernard probably has a late 80s- early 90s Ford or Chevy work van. I imagine light blue personally.

Guy Feldstein probably drives a tiny old toyota pickup. Quality but cheap (for it's day).

Whit probably has a flying car prototype around somewhere, but daily drives a 90s sedan.