Oxford is within decent distance from Tilghman's. Mears has a pool. At least 3 good restaurants (Robert Morris Inn, Pope's Tavern, Latitude) plus another I can't remember off-hand. That's getting further way, though, and you'd be coming back through the Narrows (or around the south).
Or Deale; Herrington Harbor North. Serious pool, extensive grounds. Calypso Bay restaurant on site, plus lunch via dinghy
to Skipper's Pier.
Or Galesville and the Rhode River. Anchor in the Rhode, commute to town. Very small, but two decent restaurants.
DO HUG THE R4 as you enter Knapp's from the Bay. Skinny water
plus shoaling. Most everyone can get through, one at a time; crossing while near the R4 probably won't cut it for one or the other vessel.