Rock Hall is one of the few remaining watermen's town on the Chesapeake, (although even it is beginning to give way to the pressures of development and tourism.) Rock Hall is a well protected harbor, mostly due to a very large sandbar that runs down the eastern shore, so beware when approaching from the west to make sure your round to the north or south of the well marked sandbar.
Waterman's Restaurant is a favorite crab house on the Chesapeake and offers free transient docking if you stay for a meal, but there are also plenty of marina's offering full services nearby. The town trolley picks up visiting boaters (and their bikes) just outside the restaurant on a regular schedule for a few dollars per head.
Rock Hall has a burgeoning antique and artisan community, which makes for a fun exploration and the Waterman's Museum has a fine reputation.
Just outside of Rock Hall is some of the best fishing on the Chesapeake. If you ask around nicely, some local old-timers may advise you on exactly where to go given the day's weather conditions.
If you want to end your week's exploration in quiet splendor, the north side of Swan Creek is a favorite Chesapeake anchorage due to the pretty combination of marshes and farmland.
See http://www.rockhallmd.com/ for more information.
Image above: Rock Hall patent tonger, MD Watermen's Association
Smith barely mentions Rock Hall, although presumably he stopped here and met with the Ozinie Indians. He named what is today Swan Point, Poynt Bourne after James Bourne, a member of his crew who participated in both Chesapeake Voyages. Bourne is listed as a Gentleman.
From a Map of Virginia:
"Next them [Tockwogh on the Sassafras] is Ozinies with sixty men."
From the General History:
"The Sasquesahanocks river [Susquehanna] we called Smiths falles; the next poynt to Tockwhogh [Sassafras], Pisings poynt; the next it poynt Bourne. Powells Isles and Smals poynt is by the river Bolus [Patapsco]; and the little Bay at the head Profits poole; ... after the names of the discoverers.
In all those places and the furthest we came up the rivers, we cut in trees so many crosses as we would, and in many places made holes in trees, wherein we writ notes, and in some places crosses of brasse, to signifie to any, English-men had beene there. "