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1) I have ridden the MAD Ride once, the 65km road ride.
The main reason to join the MAD Ride is that it is cheaper than other compatible rides. Other reasons are that it is not crowded, not stressed and the organisers are friendly. This ride is for all comers with a hint of hard core in the mountain bike and longer road sections, this makes it fun to attend because you can compare your bike with others and talk about the best tyres, brakes, frames etc. for each situation.
Advice for 1st time rider, would be to be prepared for all weather, make sure you take compact sunscreen, a raincoat (breathable so it doesn't sweat on the inside) and light weight layers for wind protection (arm and knee/leg warmers are worth it for their lack of weight). Distance riding is about concentration and perseverance, the speed you travel at in this event is not important.
I would add that the MAD ride is easy to get to from Melbourne and the short family event is good because it can show young kids and beginners that cycling is fun.