What would inspire you?
Cyclists, what event/facility would inspire you to ride? Most of us ride now to commute and/or do errands and sometimes exercise (I blush). What would it take for you to just hop onto your bike and around just for the sake of riding and be really happy about it? Is it something you would implement yourself or would City Hall have to do it?
I have always loved Critical Mass because it takes all of that pressure away from the ride. You lose all of that worry about who is behind you and you can sit back and enjoy your surroundings.

Here are some things that inspire me to ride:
It really doesn't take much for me though. I think I may be addicted to the feeling that you get when you combine a bit of adrenaline with air rushing by.
Not that anyone asked, but I try to avoid a ride when
What inspires me? The horizon. And what's beyond it. The exhilaration of motion, the interplay of senses, the novelty of new experiences and faces. Ironic how the most inspirational rides can have little to do with the bicycle itself.
What doesn't? Contrived, regimented affairs, e.g., the Ride For Heart.
I already feel so happy and inspired to be pedalling. Its the simple joy created by the bicycle itself. Sunshine can inspire, but the thrill of splashing through puddles in a rainstorm can be great too. I think whatever the weather its just a feeling of being alive created by the elements.
Things the city could do to make it even better - Fix potholes. Zero tolerance policy for aggressive behaviour towards cyclists. More restrictions on private car use and parking so the roads don't end up an impenetrable gridlock jam (yeah the bicycle is small but sometimes not small enough..)
Things that would screw up joy - Mandatory helmet laws. Crappy bike lanes (prefer none to a bad one - ie too narrow, filled with debris and badly maintained)
Dreamland - Have a major route (say Queen) pedestrian/cyclist/transit only - or at least priority (ie cars have to go very slowly and yield to all other users)
I enjoy both riding or taking a brisk walk through interesting Toronto neighbourhoods, I feel more connected with people and often catch myself grinning like a fool.
Eliminate street parking on main roads.
Triple the cost of parking permits, it's ridiculous I can leave a car 24 hours a day in the way on a public space for only $10 a month.
Introduce a federal carbon tax, plow billions more into transit and bike lanes.
Bring back the Yonge St. pedestrian mall we had during summers in the 70's and extend the idea to a couple of other areas.
My favourite rides have all been in Montreal. The Tour de l'Ile (1985) was a great ride - I think it was the first ever. Riding along the wide bike path to St. Catherines, with the canal on one side of the path and the river on the other (too bad the trees don't create any shade). Crossing the bridge from the South Shore, through the Parc Jean Drapeau, to the Old Port for a day in Old Montreal. Riding the Lachine Canal path at 1:00 in the morning.
I've had fun rides in Toronto also, where we've picked a route on the bike map and set out to explore. The one problem I've run into is overcrowding on bike paths. I keep meaning to take the subway to the inner suburbs to see if the bike paths there are a bit less crowded.
So what do I need? Great bike paths or a fun event. One that goes through city streets is more fun than a ride along the DVP.
I like riding almost all the time. But these days I do quite a lot of my riding with my daughters. I know a good ride when my kids had fun, and they talk about doing another ride like that again soon.
My eldest daughter came on just a few more rides with me last year than my youngest. She talks about a couple of those rides quite a bit, like getting pancakes at Nathan Phillips Square, and visiting the ROM after we finished the Bells on Bloor ride.
The girls also really enjoyed being on a Critical Mass ride, until my youngest fell because of the streetcar tracks. But we gave our girls some lessons on a section of Dundas that had been closed, so now they can ride on/beside streetcar tracks.
My girls are motivated more by the destination than the ride itself, something that I have to keep in mind. In order to keep a ride fun for the girls, there has to be some "reward" that is part of the destination. The ride-for-Heart only became fun for the girls at the end, where the big-to-do was happening; it was only after having fun there that my daughters who suggested riding all the way home even though we promised them that they had finished the ride. A destination can sometimes be a simple as a visit to a "candy store" (or any well stocked variety store) for a treat. But it is more fun for them (and Jen and I too) when we get to do something at our destination, like ride the rides at the Island, look out the CN Tower, eat a breakfast at Nathan Phillips Square, or go for a swim. But they also enjoy riding to go shopping with us (as long as we feed them) and to get to their "lessons" (swim/skate/gymnastics/whatever). Although they really look forward to visiting and playing with their friends, and making new friends wherever they go.
Now that I have finished writing this, I realize that my kids are a lot like me. The experience is a gestalt. There's a satisfaction in a destination but is merely on part of the experience; the ride becomes another part of the experience. The experience is greater than the ride and the whatever the destination offered.
As for the rides themselves, we most enjoy those rides that have allow us to journey on comfortable roads, where we don't get honked at, squeezed, or whizzed by too close by motor traffic. And parking; we've got to have a good place to park our bikes, whatever the destination. Not enough places have any bike parking, let alone enough or decent bike parking. So the city could provide more bike lanes, better enforcement in the bike lanes we have, and more bike parking.
But the very best best rides, the most memorable experiences, were on those rides where we met up with old friends and made some new ones somewhere along the way.