Making a ride more of a challenge

[Will Spin]

Take one wheel off

 

[NorthernDave]

Take one wheel off

Ideally the back one to make it a real challenge.

 

[screenman]

Naked, sure will get you some attention and possible a sore bum.

 

[Sunny Portrush]

Don`t eat or drink anything and then wonder why you`ve run out of energy (I may have done this at the weekend)

 

[Specialeyes]

BMX bike or Raleigh Chopper?

 

[Shut Up Legs]

Dress the first group up as robbers, the second group up as cops, and ride along to b̶a̶n̶j̶o̶ ̶c̶h̶a̶s̶e̶̶ Benny Hill music.

 

[Yellow Saddle]

Find a pair of vintage Levi's with a crotch rivet and do the trip in that.

 

[Drago]

Smear your saddle in Deep Heat.

 

[Shut Up Legs]

Here's a way to make the ride very challenging: ride the Backwards Brain Bicycle (and good luck with that: you'll need it):
http://www.smartereveryday.com/store/backwards-bike

 

[CanucksTraveller]

You've got many fine comedy suggestions.
One serious one though, see how much weight you can lug in a trailer. Or do the comically bad wind resistant fancy dress attempt... one drawback is that only your fellow cyclists will appreciate how hard it actually is. Imagine the drag coefficient in this outfit.

 

[alicat]

Just relax and enjoy the company and the views.

 

[Flick of the Elbow]

Wear a woollen jersey, ride a 531 frame, and use 36 spoke hand built wheels without anything aero. And carry a comprehensive set of tools and spares. That should be enough of a handicap against the corporate sportive types with their speedsuits, their carbon fibre aero kit, and their faith in their mobile phones to summon a lift home if they get a mechanical.

 

[Fab Foodie]

You could challenge yourself by going with the slowest group and helping and encouraging the least able?

 

[Shortandcrisp]

You could challenge yourself by going with the slowest group and helping and encouraging the least able?

This and stay in a really low gearing spinning like a whirling dervish all the way round.

 

[Markymark]

You could challenge yourself by going with the slowest group and helping and encouraging the least able?

...better still, blast through the course, get there well ahead of the others, order an enormous steak and a bottle of fine wine. Then when the others arrive, simply raise a single eyebrow of contempt and ask "What kept you?"