This is one event to check into shuttle service to the festival site, which doesn't have lots of good, paved parking. The Jubilee is sponsored by The City of Chesapeake and Hampton Roads Chamber of Commerce. Various big bands are ensconced under a gazebo along the Chesapeake Bay. There's a great dance floor. Bring a lawn chair for resting between favorite numbers.
Admission is free.
If most of Hampton Roads' festivals are whirlwinds of activity, Harborfest is a tornado. More than 250,000 people attend this annual waterfront celebration, which began in 1976. The star of the East Coast annual waterfront spectaculars, Harborfest is a nonstop flurry of live entertainment, sailing ships, water and air shows, more food than you could possibly sample in a weekend, and the most singular display of fireworks you'll witness all year. The crowds can be overwhelming, so use the efficient shuttle service available from a multitude of convenient locations. It's held on the first weekend in June.