Hey Andrew,
I'm probably late on this reply, but just in case:
I fished the Choptank about 15 years and 2 kids ago, but here's what I can remember:
I was fishing with a friend who had a good-sized boat. We launched about 5 miles from the mouth of the river and drifted out with the tide. Didn't catch much in the river, but out past the mouth there was a large stump field. Can't remember how far out we had to go, but it was definitely a little out in the bay. We drifted over the stumps and got into a bunch of little stripers with a few keeper size fish mixed in. Seems like we caught & released a good bit--maybe 10-15 in a couple of hours. He fished topwater on conventional tackle, and I threw streamers (probably clousers) and then bass-style poppers. They liked the poppers right at dusk. :)
Hope this helps.