Annapolis, Maryland is a great place to live. We have the distinct seasons, but the winter is never especially brutal. We're an hour from Baltimore as well as D.C. and an hour and a half from Rehoboth Beach, Delaware or, if you're more adventurous, Ocean City, Maryland.
Lots of good shopping!
If you're into boating, there's no place better to live in my opinion.
Moderate cost of living unless you live right on the water.
Good economy.
Friendly people.
Can you tell I love it here?
Close runner-up is Portland, Maine, where my oldest daughter was born. It is the perfect miniature of a bigger city with the sports, culture, shopping, good restaurants, ect...but not the crime and high prices. It is unbelievably cheap up there! Right before my husband got transferred down here to Maryland we were about to close on a 3 bedroom home with hardwood floors, two car garage, enclosed porch, french doors in all the downstairs rooms, stained glass in the windows and within walking distance of the beach for $89,000
Good luck in your search!