Hi- thinking about doing around three nights in late August with my wife and two young children (will be 8 and 4 by August). I kind of narrowed it down to the Berkshire mountains or Chesapeake Bay. I know they’re quite different. Any recommendations for one over the other? We’ll probably drive there and stay for three nights or so either way. Thank you!

Where will you be driving from? I have been to both. I would go to the one that has the shorter, easier drive for you.

Hi- I will be driving from central Jersey so should be similar drive either way I suppose, depending on how far north I go into the Berkshires or how far south into the Chesapeake Bay Area.

I think the kids would enjoy being in or near the water more. Possibilities include Ocean City, Cambridge, Chestertown--all in Maryland. Also, historic Cape May in south Jersey is a good option if you haven't been there.

When I think of Chesapeake Bay I think of boating. If you enjoy being on a boat and have access to one, you would enjoy that area. If you’re thinking the kids would enjoy being in the woods, maybe hiking or playing in a lake, the Berkshires might be better. The Berkshires will be cooler, so in July or August the weather there might be more comfortable than in the Chesapeake Bay. Both the Berkshires and the Eastern Shore of Maryland have some nice little towns to explore.

I love love love the Berkshires. Absolutely gorgeous place. (I used to live in MA, NH, VT)

Sorry never been to Chesapeake Bay to compare.

Chesapeake area can be very unpleasant in the summer. So hot and flat. I suppose it depends on what attracts you. but I'd avoid it. If that's the choice there is no doubt in my mind.