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The Choptank River in general going towards its origin is beautiful. We stayed in the area last year and loved how unpopulated and free of the massive boat traffic we were used to on the eastern shore of the Chesapeake. Oxford is a cute town with some good restaurants nearby accessible via boat. Secretary has a cool restaurant accessible via boat. If you are looking for relaxing, I think you’ll enjoy the area.
I know you weren't addressing me, Josh, but I'll chime in, anyway. We've been boating on parts of the Chesapeake for the past 5 years...this past year was our first with the 242. We're currently on Middle River, which is about 10-15 or so miles south of where you will be. The further south you go from your home port, the bigger the bay gets...which means bigger boats, bigger waves. Once you get the Chesapeake Bay Bridge which connects the eastern and western shores, it can get quite rough for our boats...I only do that area early mornings and calm days if possible. If you stay in the upper bay, you have a great boat for it! Across the bay from you is the Sassafras River which is beautiful with a bunch of nice spots. Further north you can either go towards the Susquehanna or up the Elk River, both of which you will enjoy exploring. Bottom line is that you'll love the options you have.
That's got to be a good 200 mile + trip! What's your itinerary look like? Where are staying overnight?
I’d be prepared for a MUCH longer trip than 5 hours. 5 hours would mean you averaged 40mph the whole way...not possible with what you’ll hit south of Fairlee. I used to make a yearly trip from Elkton (slightly north of where C&D canal intersects Elk River) to Annapolis (around 60 miles) and I’d be lucky to average 22-24mph for the entire trip. Your trip takes you 40 miles further south in the “big” part of the bay. Good luck, sounds super fun but that’s going to be a long day!!