I get it - it's not quite the same, but my golden child younger brother was the school heartthrob, effortlessly sporty and very popular, in spite of being a total bastard to unpopular unsporty swots like me! I was bullied at school too, although it stopped when I went to a different 6th form and I was able to build up a bit of self confidence, or at least be free of negative attention for a couple of years. Not a good start in life really, and I went to university with social phobia and a total inability to network - so I see how bad experiences as a child and teen can create a vicious circle of underconfidence that's really hard to break out of, although I think I kind of aged out of it gradually.
Said golden child brother is even more popular with the ladies now that he has a cute little dog to walk in London parks - not that he needs female admirers now that he's married (to an older but beautiful and kind rich lady, naturally). Getting a dog and walking it is probably really good advice, and seems to be a proven strategy for meeting new people, regardless of one's appearance or dating track record. Could you afford a small dog, would it be practical with your lifestyle?
I love a pp's idea of joining a music group. I was on an online forum for a slightly niche kind of music (not jazz but a similarly minority interest) and I actually met and dated IRL a guy that I started chatting to on there. He was then in his early 50s with one LTR behind him, but he was painfully shy around women and had previously been a 40 year old virgin. It had been around the time that the film of that name came out, and he said that he used to cringe inwardly any time somebody mentioned it! We didn't stay together, but he was a much higher quality man than anyone I'd dated previously, and a pretty good advert for meeting someone through a niche interest. He'd never done online dating, and everyone I'd met on OLD had been arrogant or uninterested, or both. Most of them had just wanted to find a rich partner, having lost their shirts in the divorce!
It's too bad when you can't afford to go on holiday in the summer. I feel your pain there too. If you don't want to join the history society, could you spend the summer vacation working in a history museum? That's what I did when I was an English teacher, and I might well do it again. It might not be the best place to meet eligible bachelors, but you never know - and the extra cash would pay for a trip somewhere else. (Off topic, but did you ever see a really gorgeous 50s film where Katherine Hepburn plays an older American virgin, and she goes to Venice and has a whirlwind holiday romance with Rossano Brazzi? I can't remember the title, but it's on Youtube.)
Maybe if and when you join a hobby group, you shouldn't automatically discount men who are much older or younger than you, unless you're really not into that of course. Guys in their 60s really fancy women in their 40s, while guys in their early 20s are ridiculously horny and often have a similar need to lose their virginity ASAP! (I couldn't date that much younger because I have a 24 year old DS, but YMMV.)
Other ideas - does your alma mater have meetups for alumni? They tend to be in major cities, but if you're looking to meet people different from the ones in your current town, this might be an idea. They might be on the old and married side, in which case you could still use them for professional networking.
Could you teach in another state where salaries are higher, or COL lower? I'm not in the US, so no idea how feasible that is. But it might allow you to relocate somewhere where the population is less conservative, or else earn more/spend less. I'm sure you've already thought about this stuff but I'm just throwing it out there - I had much more luck with men when I moved from a stuffy dormitory town near London to a village in rustbelt France. Sometimes it really is the location that's the problem, and any single woman in your town would have the same dating issues you've had.
The only other thing I can think of is that, as other pps have said, your keenness to meet someone fast means that you're giving off the wrong vibes, too intense or whatever. I used to be good looking (I'm old now) and I know that when I was younger and tried to force the issue by pursuing men, they generally ran away from me as if I were Quasimodo - straight into the arms of more aloof, uninterested women! Such is life.