You guys are hardcore. How about winter boots? expensive yes. I have SIDI winter boots, found them to be warm if I wear wool or neoprene but not if I just wear regular cotton cycling socks. Seems like a time limit issue, 1 to 2 hours okay with reg socks, any longer and wool is necessary. Find my PI lobster mitts to be almost too warm.
Not sure about Rando ride, party night before.
Planning ascent of Mt Washington in Feb so better get used to some chill. Mountaineering class and summit attempt with a few other crazy middle aged men.