Well I think theres some misconceptions about who actually goes to races (especially in the US), the 1% corporate bankers and lawyers that make up Connecticut's wealthy class are not the same people buying tickets to the USGP or Indy (for the most part). Another thing is, with such a small state, land is a huge commodity (we can't make more of it, whatever is there is there) - and racetracks not only take up a huge amount of physical space, they also put a strain on the local infrastructure (Towns, hotels, highways, etc). And rich people are also not confined by locality - if they want to take the 458 and race they'll fly to Spa for a private track day or down to COTA or whatever. CTs cold weather makes it a poor place to race half the year so these tracks just sit there hemorrhaging money.

Add to that that motorsports are really not popular relatively speaking here in the US, and for the last 50+ years the main flavor here was oval track. F1 was always a european centric sport and IMSA is nowhere near as popular as NASCAR/Indy.

$300 was a lot to me at 15 too, when you're older it becomes easier to justify the hobby.