I'm preparing for the colder months, too. Going to order a winter riding coat, insulated PVC autumn boots and thermal winter riding boots from Germany in September. Gotta keep warm! :)
Aaand, I found I place where sulky carriages can be ordered for rather reasonable prices, so I will start stashing up my cash for one in winter, and, hopefully, will be able to buy one before the next fall! Yay! :) One comes for ~ 600$, is this considered expensive where you live? And about ~250$ for a harness.
I yesterday rode bareback and, when I asked for a canter, Snickers bursted out in a very powerful stride, I was pleasantly surprised for this energy! A barnmate who was training with her horse in the arena at the time, spooked, because she thought that he was bolting away with me, but that was not the case - I transitioned him down to trot in a matter of a couple of strides with seat alone, as I had decided to ride completely tackless.
However, I had planned just an easy hack, so I didn't ask for anything more than trot after that.
And, as for groundwork, we've hit a rocky bottom lately.. I think I've pushed him too hard and made him sour, so I have no stepped back a few steps and working on his comfort and relaxation. Makes me think that maybe we're not that ready for the horse fair after all - I wouldn't want to make a bad first impression with a sour horse that nips against pressure. :/