As for the regular pit stops, I think it would be a nice idea to have Bike to Work Day once a month. Maybe some local businesses could be convinced to donate breakfast items in return for promotional opportunities. Some of the local Business Improvement Districts could coordinate something like this.
It wouldn’t need to be as large-scale as today’s event to be effective. Maybe one day in April, May and June. Possibly September too. But I don’t think a lot of the casual cyclists will commute as often in August because of the heat.