h a l f b a k e r y
What's a nice idea like yours doing in a place like this?
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A vertical rotating shaft is driven by the rear wheel of your bicycle. At the top, about 6 feet above the road, is another gearbox with a number of exposed sockets.
You can attach a flexible drive shaft to the socket, The other end of the flexible drive is attached to the similar socket on your friend's
A big visible lever on the vertical shaft engages a ratchet clutch in one direction, the lever marked on each side "MASTER" or "SLAVE".
This equippage allows you to assist your penguin friend. Or vice-versa.
Just keep close together!
Bicycle tow rope
A commercial purpose-made version of the common retractable dog-leash tow rope [CraigD, Oct 12 2012]
||Tow ropes are an old, simpler, and I'm fairly certain more mechanically efficient way for a stronger or fresher rider to assist another.
||I've done this with about 5 m of simple braided climbing rope tied to my seat post and looped over a following bike's handlebar water bottle rack, and fond it to work well.