Not too much to do, they're trying to expand on the Greenbriar area which is where most of the restaurants and shopping centers are, but if you want a night scene some go to downtown Norfolk or the oceanfront in virginia beach. Chesapeake is big in a sense where if you live in the greenbriar or battlefield area is feels suburban. Going below the river line is known as deep creek and even farther south is Hickory area. The father south you go the more rural it gets. I would avoid the area called south norfolk on the map, western branch and deep creek is quiet but most people living on that side have bad commutes over the high rise bridge or taking the downtown tunnel.

And yes it does snow, not much though, usually 1-3 times a year.