Meeting someone arriving by car reduces the possibilities by a lot. I can think of a few possibilities with camping
Rock Hall to Elk Neck State park. distance about 31 miles.
Hoopers Island to Janes Island State Park about 34 miles. Or start at Taylors Island Creek on the mouth of the Choptank for a brutal 44 miles.
Chincoteague Virginia to Assategue MD ending at Assategue State park or Assategue National Seashore About 28 miles
Onanacock, VA to Cape Charles Virginia. There is a private campground on the coast near Cape Charles City on Cherrystone Lane. 39 miles.
Saxis, VA to Shad Landing State Park on the Pocomoke River. About 33 miles.
Then I think you could put together some trips on the Potomac following the Potamac River Water Trail which is about 100 miles long. The Patuxent River has some possibilities as there are a number of campgrounds along that river. I think you might also look at the Rappahannock. I do not know that river well but it is very long and there are a few campgrounds along its banks.
And one with motel that is self supported with no shuttle -
St. Micahels on the Miles around Kent Island to St. Michaels on the Choptank. The start and finish points here are about 200 meters apart but there is 36 miles of paddling in between. No camping however, but motels avaialable.
There are many more possibilities if you do stealth camping and do not meet anyone that night by car.