As the air gets crisper and the leaves begin to change, remember Chesapeake is host to some of the best fall festivals and activities in our region. Whether you’re looking to explore our food scene, leaf peep, hear live music, or just unwind, there’s no shortage of things to do here this season.
Bursting with Fall Festivals
Every October, folks flock to the mouthwateringly good Great American Food Fest. It’s our all-inclusive charity event that features unlimited food and drink and live entertainment by Sundawg. Guests can expect to feast on everything from BBQ pork and barbecue chicken to fried fish, clam chowder, hush puppies, corn on the cob, and more. Starts October 4

Another can’t miss? The Chesapeake Virginia Wine Festival. It’s a chance to try wines from Virginia’s 20 top-selling wineries, eat great food, and enjoy live entertainment. This year Lewis McGehee and Friends will be headlining the event, bringing the sounds of acoustic rock and folk into the relaxing atmosphere of the festival. Starts October 14

Calling all Foodies
The best time to explore our flourishing culinary scene is during Chesapeake Restaurant Week – October 13-20. The restaurants are as welcoming as they are delicious. Dine from special menus at fixed prices all day long, as restaurants will be serving a variety of offerings for breakfast, lunch, and dinner ranging from $10 to $55. Starts October 13

Pumpkin Patches and Corn Mazes
Pumpkin spice lattes and Halloween fun dominate the season but don’t forget to include a good corn maze and pumpkin patch on your must-do list this fall. Historic Greenbrier Farms is a popular spot that features a corn maze, pumpkin patch, petting zoo, and playground.
For a truly scaretastic time, check out A Haunting at Greenbrier Farms, which takes place from September 22 to October 31. It’s full of spooky thrills people of all ages can enjoy.

Have kids? They’ll love the Chubby Pumpkin Patch as the facility also boasts a playground and bounce house. Plus, its pumpkins are already laid out, so you don’t have to cut from a vine.

Farmers Markets Galore
If it’s a farm market experience you’re looking for, check out Hickory Ridge Farm, Great Bridge Pumpkin Patch, and Mount Pleasant Farms. One of the most popular spots is Bergey’s Breadbasket. They offer fresh-baked pies, sandwiches, jams, and ice cream.
The Fun Lasts Thru November
There’s no better way to celebrate local heritage and lifestyle than at the annual all-you-can-eat Chesapeake Sheriff’s Oyster and South Festival. It’s a time of year when the community comes together to enjoy live music, delicious seasonal oysters, and a wide array of cocktails and beverages. Everyone’s welcome. Starts November 11
Learn more at VisitChesapeake.com/fall.

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