17 Awesome Things To Do This October In The Chesapeake Bay Region

Like putting on long sleeves and packing away the swimsuits—or sipping pumpkin flavors drinks—the Chesapeake Bay Region in October is a treat we eagerly wait for all year. The fall festival is in full swing, the oysters are ready for shucking and the entire Chesapeake Bay is looking for that evening throw that signals summer might be slipping away. Here’s the only to-do list you need this October. 

1. Whether your preference is a bass, bow rider, cuddy cabin, downeaster, or runabout, the United States Powerboat Show will allow you to explore your inner mariner. Thu, Oct 3 – Sun, Oct 6, Annapolis, MD. 

2. From bluegrass pickin' to wailing blues, folk festivals honor folk music and Americana. Grab your listening ear and hear to the Richmond Folk Festival on Fri, Oct 11 – Sun, Oct 13 in Richmond, VA. 

3. An apple a day keeps the doctor away, so here’s where you find the best apples! Visit the Darlington Apple Festival on October 5 and join in on apple cider, apple picking, and apple pie!

October is Seafood Festival Season and we are lovin” it.  Crabs, oysters, clams, mussels, and fish are rich traditions of the Chesapeake Bay.  These are the seafood festivals for you to enjoy in October.

4. A Taste of Chesapeake City on October 5. 

5. Rock Hall Fall Fest - Celebrate the Oyster on October 12
6. Oysterfest 13 by Ryleigh's Oyster – Baltimore, October 12,
7. Poquoson Seafood Festival – A Salute to Watermen on Oct 18^th. 

8. Holly Point Art and Seafood Festival on Oct 19^th in Deltaville. 

9. As the leaves turn colors and the vegetables become autumnal; the flowers of fall have their own colors that liven up the garden beds. These will be showcased on Oct 3^rd at the 2019 Fall Flower Festival in Virginia Beach, VA.

10.   Kayak along the fall colors through the Indian Water Trails on the Eastern Shore.  Bending Water Park has miles of unspoiled wetlands and plenty of history to explore.

11.   Corn field mazes are the official end to corn on the cob summers but they bring us so much fun in the fall. Head to Mechanicsville to check out the Forrest Hall Farm Crazy Corn Maze.

 12.  Aside from corn mazes that bring the fall fun, pumpkin picking is the best! Visit Bowles Farms Corn Maze & Pumpkin Farm in Clements, Southern Maryland for picking fun.

 As the weather turns so does our hankering for seasonal drinks.  While we love summer food, these next events will prime us for great fall beer and wine options.

13. Fall Wine Festival & Sunset Tour, Oct 11^th in Mt Vernon, VA 

14. Wine and Food Tastings, Oct 26^th, St Michaels, MD. 

15. Chesapeake Virginia Wine Festival, on Oct 12^th in Chesapeake, VA. Love the tag line of “red, white and blush”! 

16. Virginia Beach Craft Beer Festiva, on Oct 19^th and 20^th in Virginia Beach, VA. 

17. Annual 757 Battle of the Beers - 757 different breweries on Oct 12^th in Virginia Beach, VA