2 prs. of boots & stuff for 2 weather conditions

[shootingstar]

So, between clothes, shoes and gear, we're going to have to pack a fair amount. But I realize there are worse problems to have!

Absolutely right, worse things.

Just to clarify: I wear a different pair of boots for walking around town compared to the boots for snowshoeing. Haven't spent time to find nor want to spend a lot more money for another (2nd) pair of boots for snowshoeing... So I use a different pair of boots for walking around town. Otherwise I will have blisters and tired feet.

I wear customized orthotics.

So for a 3 day trip: 2 prs. of boots + 1 pr. of clean flip flops for inside hotel. I don't like walking all over hotel room in bare feet..yes, to me, I doubt those floors are really that clean, except for the bathroom which is not carpeted.

(I don't wear shoes, except occasionally, slippers, inside my home..this is how I was raised as a kid.)

[Crankin]

I definitely don't wear my winter hiking shoes for "walking around" town. When I am going up north (Vermont, about 15 miles from Quebec border), NH, or western MA, I usually wear my Merrill Mocs in the car, up, or my Uggs that are nice enough for going out. We also usually stay in places where we eat dinner at the inn, which is very nice if it's below 0 degrees F. So I have a pair of shoes for that, my hiking boots, x country ski boots, Uggs, slippers. It's just what we do. We usually put all of our "outdoor" shoes in recyclable grocery bags, as well as the hats, gloves, liners, gaiters etc that we need for actually doing the sport. So, in the AM or the night before, the stuff is easily accessible and I don't have to dig through a suitcase to get it.
I bring a variety of wool socks for different conditions and x country skiing/snow shoeing. My hiking shoes are about 8-9 years old and very broken in, but 2 years ago, I got terrible blisters while snow shoeing in Stowe, because I was wearing x country ski socks with them. Lesson learned.

[shootingstar]

I wear walking semi-dress knee-high boots that are lined. It can get cold here in the mountain towns. Last year it was -25 degrees C when we walked around on some trails for 2 hrs. Maybe one day I'll get around to the time consuming search for hiking boots @right price @not too non-blistering.

The multiple shoe thing becomes a somewhat a pain in the butt especially bike touring when we do our own route and self-supported: on some trips I've worn my bike shoes, brought along light running shoes for lots of walking around and the flip flop slippers for showers/hotel rooms, etc.

Running shoes are better for me with a customized orthotic and light hiking.

It's better not to think about the extra weight of bike pannier weight. I gave up on dress or semi-dress shoes...a looooong time ago for vacations.