Lorne Greene

We are thinking of moving in the next few years. NC is a bit too hot for us, we would like someplace on the bay near the water with a downtown area that is old and cool. We both enjoy living in older homes with some history. So far we have considered Annapolis but the parking situation there and taxes to live downtown are more than we would like to deal with along with the prices. We like St. Mikes, and Cape Charles VA so those are on the table. We have yet to visit Chestertown, MD to check it out. Does anyone have any recommendations on places on the bay that have that type of vibe that we are not aware of?

CaptWilly

St. Michaels, if you can afford it. Oxford is nice too and rather quiet.

30Concept

Easton is consistently rated as a great place to live. Check out Cambridge too.

drumsfield

Rockhall, Oxford, St. Michaels, Cambridge, Kent Island, Chrisfield, Solomons, Chesapeake Beach, North East, Chesapeake City, Elkton, Easton, Shady Side... lots of places.

croakerpoker

Old town Portsmouth could work. And if you miss the inner city vibe you just have to walk a few streets.

old hat

Easton area ( St Michaels, Oxford) is less sleepy than some of the other area’s with a more vibrant downtown. My wife is an artist and loves the Plen Air arts festival along with the restaurants. Chestertown is a nice college town and there are some great surrounding area’s along the Chester river and down to Rock hall. The one draw back to this town for retiree’s is the hospital is now just an urgent care center and you have to go all the way to Annapolis, Easton or Dover for a real hospital. Good call on Annapolis as it is way too busy, parking sucks but the restaurant scene is very good.

shoreboy6

It really depends what you are looking for, your budget and how close you want amenities. I live near Chestertown and grew up in Town. Very historical downtown section with some new and newer stores/restaurants. In town taxes are a little high but not the highest on the shore.

St. Michaels is a great little town also with a lot of history and a lot more in the way of things to do but it is pricey and gets plagued with tourists.

It might be worthwhile to make some weekend trips and stay at a B&B in the towns you are interested in to get a good feel. There are plenty of old little waterfront towns and communities up and down the Bay that could be considered. Not sure where you are from but the Eastern Shore is a good 20-30 years behind the Western Shore and I consider that a great thing. Just realize you will have to travel to get basic things depending on where you are and there probably aren't chain stores on every corner.

muskrattown

Just a FYI lots of people in the areas mentioned own dogs.

Fish'nFool

You don't have to live in downtown Annapolis to enjoy the benefits that you describe along with the convenience of enjoying access to downtown. In fact my wife and I are going to head into downtown tonight by boat to grab some dinner. On top of that we have access to lots of other cool spots e.g. St Michaels, Kent Island, Stevensville, and other nearby water oriented locations. Naptown area has a little more to offer then some of the other locations mentioned. Moving to rural while nice will hinder convenient access to other great spots that you may find you wish you lived closer. But if more rural is your thing, by all means the eastern shore or even southern maryland e.g. Huntington (50 min south on the bay from Annapolis). Bridge traffic in the summer sucks so keep that in mind as you consider locations. Some locations you will effectively become land a prisoner in your own home because you can't drive anywhere Thurs - Sun. I live in Annapolis, but not downtown and appreciate the more centralized access to the east, west, south and north.

usernamewastaken

How important is fishing to you? If it’s high on the list I would choose Cape Charles. Much more diverse fishery as you get closer to the mouth of the bay. Also......Maryland politics are something to consider too. I could never live there. They taxed rain there not too long ago.

BoatsnHoes7

politics in every thread

Lorne Greene

I don’t fish. We are cruisers and I am well aware of the guns I’ll have to sell before moving.

shoreboy6

I wouldn't worry about selling any guns.

Another consideration is taxes. I really don't know anything about how VA taxes retirement but it may be worth while to check out lower DE. You could still be rather close to the Chesapeake and I prefer the section of Lewes down to Fenwick.

KismetLRC

We love the Kilmarnock, VA. Small quaint town....low crime.....low taxes.....keep your guns (actually, guns encouraged!). Just don't come here telling us how you did it where you came from.
Lot's of deep water cruising. Miles of shoreline. Very reasonable home prices (or into the 7 figures if you're so inclined).

PeteVB

Cape Charles, anywhere in MD is going to be a suburb of DC/Baltimore. cape Charles is a sleepy coastal town, not sure it will be noticeable cooler than NC though

Lone Ranger

I'd stay away from the Western Shore of MD.If You consider Md. Eastern Shore is Nice..I I could, I would be on the Eastern Shore of Va.

30Concept

I live in Charles County MD, and considering moving to the Northern neck of Va. Property taxes and home prices are higher in MD, income taxes slightly higher in Va, Va has personal property taxes too. Pick your poison, it depends what you own.

I was pretty shocked at the prices of waterfront homes on the eastern shore.

TorFed

Cape Charles. Stevensville. Chestertown.

TurdFerguson

Lots of cool old farm houses pop up in Cape Charles all the time. If I had the ability to move out there I'd be gone in a heartbeat. Rural, on the bay, away from busy people.

Timex

Lots of history along the western Shore of the bay as well don't overlook that area