The Eastern Shore of Maryland is scattered with interesting small towns and natural areas within easy reach of St. Michaels. Tilghman Island, about 12 miles south via Route 33, is a working fishing community where skipjacks — the last commercial sailing fleet in the US — still go out in season.
Oxford, accessible by a short ferry ride across the Tred Avon River from Bellevue (about 8 miles south), is another beautifully preserved colonial town with waterfront restaurants and the oldest free-running ferry in the US, operating since 1683.