Listen online and find real oldies stations that play 50s , 60's music. OTA radio generally won't play the music we like, because the advertisers don't want listeners who are over 49 years old, and generally doo wop listeners are pushing 65-70+. Same with other forms of music that OTA radio won't play for the same reason (Big Band, Standards, Classic Country, Real Oldies (50's - 60's), Classical Music, Jazz, Western (think Son of the Pioneers), etc.
Remember the listener is the product, the advertiser is the buyer. The advertiser wants young folks who will believe their commercials and who don't have loyalty to a certain brand ( for example I've driven Ford vehicles and no matter how much Toyota advertises, I'm not interested). So even though the Baby Boomers have money to spend, they don't want us for that reason. NO problem as far as I'm concerned. I do listen to sports talk at work (WWTX, WIP-FM, WPEN-FM, and WENJ 97.3) as a great alternative to listening to the same ole BS that is Rush/Beck/Hannity or the local Rush wannabe and the other political talkers.
I also listen to audio books ( I work alone in a lab so I can get away with that). Most radio stations offer listen live buttons, so you could find a station you like in another city and then listen to their station online. I also listen to online music where I can pick what I am in the mood for on that particular day. ONLINE Radio is a great thing. I even listen to my local AM stations online (WDEL, WWTX, WILM, WNTP, WPHT), because then they sound like FM.
You seem to like the older oldies so why not listen online to WVLT, but there are other online choices.
Now if you're talking about riding in your car I just listen to either sports talk stations (we have 4 I can get in my area) or listen to a talk station or NPR. Sometimes I listen to the CLassical Music station in our area, but other than that, I'm listening on line quite a lot.