Late spring and early autumn are the best times to visit St. Michaels. May and September offer warm weather, good crabbing, and far fewer crowds than the summer peak. Summer (June–August) is busy, particularly on weekends, with traffic on Route 33 and waits at most restaurants.
The Chesapeake Bay crab season runs from April through November, with the best crabs in late summer and early autumn when the water is warmest. Oyster season starts in September and runs through spring — the R-months rule applies, and the winter oysters are excellent.