Antique and unique vehicles come out every fall for the Chesapeake Classic Car Show


Some of the most unique festivals in the Hampton Roads area happen to take place right here in Chesapeake, VA. Fabulous festivals occurring throughout the year range from family-friendly events to foodie smorgasbords, all set in the beautiful scenery of our slice of the East Coast with the welcoming atmosphere Chesapeake is known for.

Outdoor Adventures

Watersport fanatics, get your paddles ready for KayaXpedition. This kayaking festival takes place in Oak Grove Lake Park and offers classes for beginners and races for more advanced participants. For those looking to support friends and family from land, music, food, and other summer activities are also available.

Food Fests

The Great American Food Fest has the traditional grub you’d expect at an all-American cookout. From barbecue chicken to corn on the cob, fill your plate with all different kinds of meat, seafood, and veggies, but make sure to leave room for dessert. Need a break between bites? This event offers tons of terrific entertainment, including kid-friendly activities for young eaters. 

In search of some vino to pair with your meal? The Chesapeake Virginia Wine Festival has got you covered. Each October, gather with grape lovers to toast over 200 wines available in the region and pick up a bottle or two while you’re there.

The end of July brings the Blue Crab Festival, where visitors can get their fix of all-you-can-eat crab along with barbecue pork and tons of beverage options. Make sure to show up hungry, since coolers and carry-out are not permitted.

Family Fun

For art lovers of all ages, the Virginia Arts Festival is your pathway to culture. With world-renowned dancers, Grammy-winning musicians, and even Oscar-winning actors make sure to book tickets to one of the many exceptional performances happening in the Chesapeake region.

Celebrate BikeFest each May with more than 12 miles of paved trails, an on-site mechanic, maintenance demos, and even a bike rodeo. Folks from the Chesapeake Bicycle/Trails Advisory Committee will be around to advise riders, help with safety questions, and promote a variety of routes in the area for cyclists.

These are just some of the many festivals you can attend in Chesapeake. Be sure to check the events below to see which festivals are taking place when you’re in town.

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