www.3Peaks.co.uk

I took my son caving last year as part of the OverGround-UnderGround festival with http://yorkshiredalesguides.co.uk/ I assume they could help

That could be two circular walks both starting and ending in Horton, its easy to see the footpaths on the OS Map . But if its not too far for the first group I would consider following the three peaks route from the top of pen-y-ghent to Birkwith, then turning off that route and going to Selside. Fr...

Organising that many people is quite an undertaking - and some responsibility. I am surprised that a company would do it without professional organisers - just from a health and safety perspective. Remember that by mid October there will not be much more than 12hrs of daytime and sunset will be arou...

If you are walking with a guide that will take care of most of the usual safety warnings. So if I had to pick one piece of advice I would say make sure everyones boots are well broken in. One person getting sore feet can really slow a group down and make the whole experience miserable.

Company is always good.

If you don't find anyone the route is well trod at that time of year. Set off as early as you can and there should be plenty of people around for most of the walk. Both of you can carry a phone, torch, whistle etc incase you get lost and separated.

Boots are quite heavy, though I've never weighed mine. 1kg each does sound quite heavy. Probably the most important thing is to get them well worn in. Not just tramping round the house, but a few walks of a few miles with a bit of ascent and descent. That breaks the leather in and will tell you if t...

Sounds like you are getting prepared in advance - so you should find your way.
Just check the weather and take the appropriate kit with you. Low cloud can disorientate even the best.

Personally I prefer boots. But plenty of people wear these shoes. They would only be more of a problem in wet weather when your feet might be more likely to get wet.
As long as they are broken in, and you've done a fair few miles in them before you start is the main thing.

Here are a couple of charity ones.

http://www.macmillan.org.uk/Fundraising ... Peaks.aspx

https://www.mariecurie.org.uk/en-gb/eve ... 2013-9084/

Bit vague.

Who did you book it with?