October 3-6 - United States Power Boat Show. This show features everything from luxurious motor yachts and trawlers to high-performance boats and offshore fishing machines. Admission. Opens at 10 a.m. daily at Annapolis City Dock.
October 5 - Grace EP Fall Festival & Car Show. The event offers a free moonbounce, free pony rides, free face painting, free kids activities, free food and much more. 10 a.m. - 2 p.m. at Grace Evangelical Presbyterian Church in Davidsonville.
October 5 - Wine Tasting to Benefit Goshen Farm. Enjoy a hand-picked selection of three red and three white wines, provided by Bellas' Liquors, as well as some tasty hors d’oeuvres prepared by Chef Art Lewis of Culinary Art. 4-7 p.m. at Goshen Farm in the community of Cape St. Claire in Annapolis.
October 5 - A Singable Feast. The Annapolis Opera will begin the season by celebrating opera at our wonderfully successful annual dinner with food and wine matched to the arias to be performed by guest singers. Event begins at 6 p.m. at Loews Annapolis Hotel.
October 6 - First Sunday Arts Festival. Last of the season! It's Street Festivals, an Art Market, an Entertainment Venue and a Arts and Craft Fair all rolled into One Fun First Sunday Arts Festival. 12-5 p.m. at Calvert and West Streets in Annapolis.
October 11-14 - United States Sailboat Show. Now in its 44th year, the United States Sailboat Show, attracts more than 50,000 boating enthusiasts from around the world to the waterfront of historic Annapolis. Admission. Opens at 10 a.m. daily at Annapolis City Dock.