I would like to be able to use a trailer, either open-air or enclosed to transport multiple bicycles at the same time. When I google hitch racks the maximum is 5...I am looking for a towable option...do these exist? Where can I find one? Could I make one?
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Absolutely. With a trailer, you can do just about anything you want. With a powerful enough vehicle, you could tow 120 bikes if you felt like it and had the money to build the trailer.
Go to a northern tool, fleet farm, or some similar store that sells trailer parts, and you can build up a trailer as big as you need.
You can use parts like these: http://yakima.com/shop/bike/truck-bed/blockhead to provide fork mounts for your bikes. Otherwise, you can fabricate fixtures that can hold the bikes with front wheels attached.
I once constructed a trailer that could in theory handle 8 bikes. Used it for family biking and for Boy Scout activities. I used a standard 4x8 utility trailer as the base, and added removable uprights that the bikes could be strapped to.
The hard part is finding some sort of mounting scheme that can accommodate bikes of different sizes and styles (and do so reasonably cheaply).
Where I live it is common for commercial operator to purpose build trailers for carrying bikes such as these.
The other option I have seen is custom bike racks for back of any flatdeck trailer or trucks.
One event here has over 1000 entrants to a relay - they need to transport 1500 bikes on the day, up to 100km..... So it's certainly doable.... I am glad I don't do their logistics planning...