Make the first weekend in November a racing weekend. The Chesapeake Shorthanded Sailing Society will host the Last Hurrah on Nov 1. The race starts/finishes when there is good wind mid-West River and sails out to Thomas Point and back.
More info and registration at https://www.nextsailor.com/app/page/regatta/806
Cheers!
Douglas Ellmore
Commodore, CHESSS
s/v REVOLUTION