Usually I have been planting my fruittrees on the spring, but have been told fall is better
So we just planted 68 trees from small to medium size the last two days. I watered them in and put old hay around them to help block grass. We put stakes next to each one so we don’t forget where they are at.
Do I need to water like I do in spring? Or due to colder weather and no foliage, do I wait for rain? Scheduled to rain tomorrow.
In my experience it is generally a good idea to water at planting time even in cold seasons, even making it somewhat soggy has its use (to drive out pockets of air - water before the hole has been completely filled in and then shake the tree around a bit), just don't make it a swamp.
If there are many potentially nibbling critters around then you better delay the laying of mulch around the young trees until spring (and possibly wrap the lower trunk in some wire mesh).
Watering in a freshly planted tree is the right thing to do, always.
It is preferred to plant dormant trees while they are still dormant, that way the wake up in their new home and start sending out new roots.
I always try to plant new trees in the winter time or just before winter, I usually get a price break too, since they would rather have new stock coming in spring and cost of winter trees in a nursery means time and money lost to care givers and water company.
With newly planted trees, don't put any mulch near the trunk, that invited voles and other bark nibblers to have a free meal in the wintertime.
As with all plants, roots survive really cold temps better if the soil is just damp enough. That means you might need to water them should you find their soil dry, it is time to water.
The one problem is like Crt Jakhel mentioned, a ring of 1/4 inch wire mesh around the trunk, not against it, will help and then no mulch within 6 inches at the minimum.
Most trees won't worry about grass growing out away from the trunk anyway.
You did not mention what hardy and climatic zone you live in and if the ground gets frozen during the winter months.
Obviously, if the ground is frozen, then no need to water. You want to water before the ground freezes for the winter.
Also, if you get lots of rain before the ground freezes, then you do not have to keep watering if nature's rain is sufficient.
I would mulch no matter what but protect my trees with a metal screen to keep the voles etc. away. The mulch will protect the roots from the cold and keep moisture in the ground so less watering is needed.
You can always do a finger test weekly to see if the ground is dry, moist or soggy and adjust your watering accordingly.
I just started planting my bare roots in the fall. I did five apple trees, watered in and mulched to within 3" of the trunk. I won't water again but the trees I just planted are in a heavily chipped area. My mentality with watering is I want the tree to force roots so I won't water again in my zone. I also planted eighty willows that I rooted. Those I did water because they had really tiny tender roots. I planted some ornamental stuff last year in the fall and it exploded in the spring, mostly Perrenial bushes like butterfly bush, daisies etc...they did really well with fall planting.
I've been watering really heavy when I plant and then every ten days if we don't get a good rain.
A weed is but an unloved flower. Ella Wheeler Wilcox
That is a really big piece of pie for such a tiny ad: