traveler24

Will be in Annapolis Oct 1 to 8th.--stressful meetings!!!
Need advice on areas on either sides of Cheaspeake Bay that would be quiet and relaxing. Have been told that areas around St. Michaels, Oxford &Easton are beautiful but often crowded???? Any opinions or insights about some "restfull"areas. Really not interested in Western Maryland as have covered that area in previous trips.
Am traveling alone and have use of car..
Looking forward to your opinions!!!

bookhall

Crisfield (on the eastern shore) is off the beaten track. Too, you can also catch one of the boats over to Smith Island. And you can do it as a day-trip or overnight.

PamSF

Chestertown is nice and very quiet. We chose it because it was described as as"architectual gem bypassed by the masses on their way to St Michaels and Ocean City. We stayed at the Imperial Hotel. Do try for a room close to the front porch. Eat at The Blue Heron and I'd suggest the crabcakes.

Owen_ONeill

Oxford is uncrowded and very quiet. there are only a few restaurants and cafes, a small general store, an inn and perhaps a hundred houses. There are five marinas in town and most of the sailors are just there to get supplies or use it as a departure point for exploring the bay. We had a very restful and romantic weekend there. We did drive over to St. Michael's for lunch one day and found it to be crowded, touristy and not appealing for our tastes.

LN

The Annapolis Sailboat Show starts on Oct 9th so there'll be a extra amount of traffic in town just for that.

Oxford is a very pretty town and often forgotten but once you see the Robert Morris Inn you'd be very pleased. Another pretty area is Tilghman Island, and ofcourse, St Michaels, then north of Rt 50 and 301, Chestertown and Rock Hall. Most of these have good internet sites showing their B & B's.

There is a great new Hyatt over in Cambridge (or Easton) and it's a pretty big hotel on the water. They had some problems getting good help in the beginning but I've heard that's been pretty resolved.

Have a wonderful time and come back again to Maryland!!

Jon_Eric

I liked all the aforementioned places, but I never found any of them to be overly crowded; St. Michaels might've come the closest, but they also have the nicest hotel - The Inn at Perry Cabin. When I lived in the DC area it was popular to discuss if Maryland was North or South. Technically its South, but people who live there dont all agree on this Well, my first trip to the Eastern Shore convinced me, its SOUTH Oh, btw the time you'll be there should be perfect weather wise.

MisterHobbs

Princess Anne is lovely, quaint, great architecture: Colonial, Federal and Victorian. Great antique shopping. Wonderful B and B's.