Where will you be hiking?

I’ve hiked and snow shoed all winter in keens, Oboz, vasque, solomon. Needless to say we deal with a decent amount of snow in Alaska so a good pair of gaiters helps a great deal. Merino wool socks and fox river sock liners are fantastic to have. 5k isn’t long enough that you really have to worry about insulated boots unless it’s going to be below -20, which I doubt you will be hiking in.