chestertown or williamsburg
 

we'll be in washington dc for 5 days then in shepherdstown (following your advice) for 5 days. you then suggested we go to the shore with chestertown as a base. is there enough to see/do there? would you suggest time in williamsburg instead? the drive from shepherdstown is around 4 hours, according to google maps. what do you recommend?
thanks.

Why did you tag this Washington,DC if you are asking about someplace else?

i have no idea. sorry about that. do you have a suggestion?

I live in Chestertown. What do you want to see/do? There is a huge difference between Chestertown and Williamsburg.

willis, don't worry about tagging it DC. Your post is in reference to your trip to DC. I skimmed your previous post so if I missed something in it, I'm sorry.

I live in Williamsburg so between bfrac and myself we should be able to help you out.

You said you like small towns, well, Chestertown is a small town. I love it and I think you would love wandering around it for a half a day. I don't know what else is there.

You would also enjoy Williamsburg. There is a ton of stuff to do there. I think if you are this close and you won't have an opportunity to return soon, you might want to take advantage of it and come down to Williamsburg.

It is going to depend on what you want and how much time you have.

thanks for your help. we have 5 days after shepherdstown. i doubt we'll be back to that area
soon. do you suggest splitting time between these two areas or just stay in one. we do like exploring an area for more than 1/2 day to get the rhythm/flavor of it.

Are you going to Shepherdstown in July for the Contemporary Theater Festival? It's terrific. I used to go every year but I haven't been able to schedule it recently. The plays are always thought provoking.

I would choose Williamsburg over Chestertown as there is much more to do there. Chestertown is sort of quiet. In Williamsburg there is lots of history to see and Norfolk nearby as well.

Chestertown is quiet, as Lauren said, and it depends on what you are looking for. The Eastern Shore of MD has some great small towns besides Chestertown. You could visit Easton, St. Michaels, Oxford. You could go to the beach, either Rehobeth for more relaxed old time atmosphere or Ocean City for the opposite. There are a lot of options but I don't know what you are interested in. There is great food to be found in all the mentioned towns. If you are thinking of touring the entire area then a more central location on the mid-shore might be a better idea than Chestertown. Easton, St. Michaels, Oxford (Talbot county) being more central. If you aren't planning on going as far as the beach, then Chestertown would work just fine.
http://www.kentcounty.com/
http://www.talbotcounty.com/

If you were choosing between Chestertown and Williamsburg, I'd have to say Williamsburg, which has way more to keep you occupied. Chestertown is lovely, but there is really very little to do there to my knowledge (bfrac would certainly know much more than I). That is, unless you really prefer things to be very quiet and restful, then Chestertown might be your choice.