Don’t know the first bit but I’d get up onto Leith Hill as starter
From there, you could do summer lightning and down into Westcott, and along the path that leads along the bottom of the N Downs, but for more entertainment I’d drop west off LH (maybe past High Ashes, it’s a wide path but potential for good speed if it’s quiet), then up to Holmbury and take BKB down to Peaslake, Peaslake back up to Winterfold and then maybe one of the Winterfold trails (Evian?)back to the bottom.
From there aim to Farley Green, Blackheath, St Marthas, over to Guildford, up to the masts on the NDW, then NDW west, cut into Crooksbury and you should be on home ground.