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If your question is, "can wind resistance be reduced for everyone on a small circuit," then the answer is "yes, this is a well-known effect, and if the circuit is small enough even one rider is enough." It is well-known that riders on indoor velodromes create their own "draft" by circling the track. This effect is large when the number of riders is large ...

If it really is an "organized" ride for thousands of riders of all skill levels, you don't really need to know/do anything special other than to be reasonably prepared for the time/distance of the ride, bring along water bottles, and bring money. And maybe sun lotion on a sunny day, or rain gear on a threatening day. But not all "organized" rides are that, ...

Anything involving more than 50 riders leaves a large impact on the area so you may want to really think about how you can be a great guest, self sufficient and most of all not in a rush. Add an hour or more to arrive early - you will be with wonderful people all interested in being outdoors together. Celebrate and take time to connect to others socially - ...

Besides talking to individuals in your local bike shops, you can look for 'recreational' or 'touring' clubs. A Google Search for Bicycle Touring Clubs turns up clubs like our club in Utah, Bonneville Cycling Club (formerly the Bonneville Bicycle Touring Club). Larger recreational or touring clubs will usually rate their group rides by a couple of measures ...

I am not sure how you would find the individual rides with the highest participation, but there are a few organizations that reach thousands of cyclists across the US by holding rides in several communities. In the US you tend to rarely see huge rides because the logistics and regulation hoops in many areas is to great to overcome. Many rides are capped ...

The London to Brighton Bike Ride organized by the British Heart Foundation is the largest UK one, probably the largest in Europe. That has 27,000 participants.

Check out the website of the ADFC bicycle club in Leipzig http://www.adfc-leipzig.de. The "Termine" link has a list of their events including bike rides. Also the "Radtouren"link might be of interest to you. Of course everything is in the German language.

Ask around your local bike shops for any groups or group rides. Then ride and get to know some of the other riders if they have kids and want to group ride with kids/trailers. The biking community here is quite large and I don't know of anything like this, I suspect once you introduce yourself to a club or group, you may need to be the driving force and ...