People used to ride bikes around Boston even before bike lanes

I don't know about this. Say more please?

Boston used to have the Mayor's Cup race in September, but hasn't in a few years now.

Both Somerville and Arlington briefly had bike races for a couple of years, around the turn of the 21st century. The Arlington race had a fatality its first year, and although they did come back for a second year, they did not continue after that. I don't know why the Somerville races ended.

I think there are a few factors as to why bike races/rides aren’t as popular as local road races.

Bike races aren’t as inclusive as a 5K in the sense that you can have a competitive class in the front of your 5K and the rest of us who want to run socially in a large group of people or maybe PR but we’re still running 10min/mile and everyone has a a good time.

Bike races either you’re racing or your not - casual is for your Sunday morning bike shop group ride. The other thing about bike races is that many of them are criterium (crit) races that are multiple laps around a circuit, like Newton’s [url=https://www.newenglanddevo.com/wells-ave]Wells Ave Crit[/url]. If you’re not riding with the pack in a race like this, you get lapped and become a hazard.

The other issue is real estate. A big organized bike event doesn’t have to be a race, it can be a ride such as the Hub on Wheels event (I think this is the one in October you may be thinking of). If you think about local road races, many are 5K, 5M, or 10K (10K = 6.1M). For a bike ride, a 6 mile ride would not be worth the time of most riders so you need bigger routes. The Hub on Wheels, iirc, has 3 route options at 10M, 25M, and 50M. That’s a lot of traffic details and support stations needed around the city.

And this is before we talk about the hard core charity bike rides like the Pan Mass Challenge and all that is needed to make such an event successful on both the organizers’ part and on the riders’ part.

Especially if you set up a relatively short crit style race, something like the BU to Longfellow to Storrow/Memorial Drive loop. Lots of public transport access, viewing areas, etc... 3 miles x 8 laps be a few hours of fun and then done.

Has been on a steep decline ever since Lance came "clean", though with a renewed interest during the pandemic, it might be on the verge of a renaissance.

That said, the major difficulty with running bike races these days is finding the $8k per cop per corner required.

I've never understood why there aren't more bike races

There ars lots of rides, just fewer races. Why? Because that's what people really want to do. Racing is hard - and dangerous when you get a bunch of rookies out there inexperienced in pack riding. Most people really just want an organized ride with a nice route - and beer after. The popularity of gravel rides is an indication of that.

This pic is giving me BREAKING AWAY vibes - the movie from 1979 about a rag-tag townie cycling team from Indiana staring Dennis Quaid and Daniel Stern. So I am going to place the year at 80-82, somewhere in Southie.

I was thinking 1980's myself. I used to do a lot of cycling as a teenager in the 80's, and this looks close. I remember hard helmets becoming common in the second half of the 80's, so this is maybe more early-mid 80's. The bike equipment does look more like late 70's, although for some reason, the clothing strikes me as more 80-ish (not sure why), which is why I was thinking maybe people in the early 80's with equipment that's a couple years old. In any case, I'm probably just splitting hairs here. Something about the photo actually looks 90's to me, but the bikes look a bit old for that, unless they were deliberately using older bikes/equipment for some nostalgia-related reason. The b&w aspect can be deceiving in some photos, since many newspapers like the Globe didn't switch to color until the 2000's.

There is a too-fuzzy-to-read (for me) street sign for the side street (relative to the cyclists) in the upper-right corner, which looks like a two-part name, like Old Colony (although I don't think it's that, but the second part does looks like it starts with a "C" or "O"). Maybe someone with better photo manipulation skills than I can tweak it, to make-out the street sign. EDIT: Actually, now that I look at it, the sign may be one of those signs designating a square or something, not a street sign, but not sure.

Those helmets look older than early 80s and by the mid 80s the cables would be running under the handlebar tape, not in the overbar loops like this.