When I was growing up there, Annapolis still had the feel of a small town, although I guess folks from a very rural area would still have considered it city even back then. And while many parts still do feel small town, other parts have changed a lot since then, and there is an area (Camp Parole and Bestgate Road/Annapolis Mall area, interesting civil war history if you want to google it), that has gotten built up with some commercial development and condo/apartment buildings. I wouldn't really consider them "skyscrapers", but they are tall buildings. http://visitatc.com/ This is just around that one area, basically a few blocks, and this is not in the downtown area. However, it's still not a city like Baltimore or DC are cities. And if you stay in the historic downtown area, you can park your car and have plenty of things to keep you busy for days within walking distance and not have to worry about traffic. Since you are not going in the height of summer/tourist season, it should be quieter, unless one or more of the big fall events are going on, as I posted earlier. So I'm not sure what to tell you, as I wouldn't consider it big city, but it's what I'm accustomed to, although I now live in a very small town (less than 2K people), so I do have something to compare it to! But I work in Northern VA/Arlington, across the river from DC and that is city to me.
Now there are some lovely spots on the Eastern shore, as other posters have described. These are much smaller towns and will be much quieter, but there will be much less to do. But good restaurants and nice scenery to enjoy. So it just depends on what you're looking for. Wherever you go, I hope you enjoy your getaway!
Now there are some lovely spots on the Eastern shore, as other posters have described. These are much smaller towns and will be much quieter, but there will be much less to do. But good restaurants and nice scenery to enjoy. So it just depends on what you're looking for. Wherever you go, I hope you enjoy your getaway!