I can only speak to the Maryland locations.
Salisbury and Easton are on what is commonly termed "the Eastern Shore" here - Salisbury is a little closer to the beach, about 20 minutes away, while Easton is a bit up the road, maybe 45 minutes away from Ocean City. Easton is very small and you'll need to drive a good distance to reach anything other than your local mall. Salisbury is a little larger, but not much. The advantages to living there is that you're very close to Delaware, which has no sales tax - many Marylanders who live in those areas drive to Delaware for their purchases to take advantage of that. Their weather is about on par with the rest of the state, though they tend to have a BIG problem with fog and rain there (more so than other areas). Not much to worry about as far as natural disasters - you're more vulnerable to hurricanes the closer you get to the beaches, but they RARELY come inland. We have maybe one goodish sized hurricane every few years, no more than that, and it's rare that it does much damage. Hurricane Sandy blew through here and it was pretty much nil - we were lucky. We've had one earthquake that I can remember (2 years ago) and we were all shocked, that's how little it happens. Nothing else. Pretty safe climate. It gets surprisingly HOT here in summer, though, and humid too since we're on the water.
Hagerstown, on the other hand, couldn't be more different. It's near the mountains (Appalachia) and it's a LOT colder in the wintertime. I mean, a LOT colder. Where the rest of the state might be in the 30s at night in the winter, H'town tends to be 10 to 15 degrees colder. Much more chance for snow, too. Hagerstown is about as large as Salisbury - some things around there, but not much, it's not on par with a large city. They do have lovely outlet stores there, though
I'm not sure I'd pick Maryland to retire to - be warned, the cost of living here is quite high (because most Federal workers live here, thanks to DC's proximity) and the taxes are INSANE. We call the governor here Martin Owe'Malley for a reason.
Housing prices here are about on par with the rest of the country - all three towns have reasonable prices, but also do not have a lot of employment opportunities in those particular areas - most drive to Baltimore, Frederick or Ocean City for jobs (depending on which town we're talking about). You can probably get a decent 2 bedroom house for under 150K if you look in the right areas.
None of these towns have a whole lot of crime. That's all in Baltimore or the DC suburbs. School systems in these areas are okay, not the best but certainly not the worst. I'd put Hagerstown's school system a little above the other two, if that's important to you. Salisbury does have the University of Maryland Eastern Shore there, if you're looking for higher education (Maryland DOES have great colleges, I can say that much for them).
Basically, if you like mountains, snow, skiing and outdoors: Hagerstown.
If you like ocean, beaches, water activities, etc.: Salisbury, Easton would be a second choice.
Also, you could try places like:
St. Michael's. BEAUTIFUL area, right on the water, near Easton.
Cumberland. West of Hagerstown, a smallish city nestled right in the mountains. Beautiful scenery.
Chestertown. On the eastern side of the bay, but higher up than Easton. Very historical!
Cambridge. A little below Easton, but larger and has more "opportunities".
Hope this helps.
[This message edited by Fireball72 at 9:38 PM, November 26th (Tuesday)]