At the moment....... road cycling, some hills, but nothing that strenuous. Go out a couple of times a week. Longest ride so far - 20 miles, but am doing 30 for the Briitsh Heart Foundation in two weeks so am increasing the mileage at the mo. Figure by June next year I ought to be able to cope with 65 miles and some more hills.
Chuffy - i see your location is on the banks of the exe and you have an Exmouth Exodus link...... that's where i grew up so I know the hills around there pretty well! (and I know what Dartmoor's like....)
Ok, next question. Are you a) reasonably fit and within a sensible weight range or b) a heffalump?
If it's a then 20 miles isn't much, that's well within 'I'm just going to pop out for a quick ride' territory - it's a start but you should be able to do a fair bit more (50ish) without too much trouble. You'll need to learn things like pacing (don't flog yourself on hills) and nutrition (drink regularly and snack during the ride) but those will come with time. 60 miles, even 60 hilly miles, should be achievable within a month or two, if that. Train for the ride by all means, but don't get fixated on the idea that 60 miles is a scary distance. It may seem that way, but once you start building your mileage it will seem much more manageable.
As Clutha54 says, it'll be as hard as you make it. Baggy and I do regular long rides (100+). Neither of us are mighty athletes but we take it steady and we get round. The trick is to do it at a pace you find comfortable and that doesn't stop you from enjoying the ride.
Try going out with other groups (CTC etc) for support. There may well be a CC social ride going out from Exeter in mid November. It'll be in the region of 50 miles, we stop for tea and cake and no-one gets dropped. You'd be very welcome if you fancy coming along.