Now you've explained a little about what might prompt such a cross continent move, i.e., now living in small rental property, where to raise a family, somewhat nearer more Eastern family...and it seems home-based employment. I still don't see why move from your nice area to another area completely strange. However, I have known more than one Californian (usually dry southern) who did move to some unfamiliar place in the green and hilly Ozarks for instance.

Oh of course...there are many attractive towns in the Newburyport and Annapolis areas...we've enjoyed places like Ipswich MA and Oxford MD and many more so scenic. You have lots of free advice!

Ozarksbill

...." called "West Annapolis"? " Yes, it is. More quiet than Eastport (in general).

One rant about Annapolis is parking. Many tourists come away frustrated about not finding a place to park and with parking tickets in hand from staying more than 2 hours in a residential area!

On the eastern side of the Bay, Centreville, Easton, Chestertown, and Denton are the county seats of 4 Eastern Shore counties close to Bay Bridge. You would be about 1.5 hours to Philly airport and about 45 minutes to Wilmington amtrak station (cheaper fare to NYC from there). On Annapolis side of the Bay, you are about 45 minutes to Baltimore/Washington Thurgood Marshall and Amtrak.

Many busses to NYC along the Rte. 95 corridor. Megabus is getting big raves lately with $1 fares if you order early enough!

Will be interested to hear what you decide!

My husband and I like the area. Close to DC/Balt, lots to do, cheaper than DC or Balt. (with those high city taxes), great medical center etc. Unfortunately, we are retiring and moving to a second home in the spring, but we will continue to come back for Camden Yards and all the area has to offer. You should check it out.