Chesapeake Virginia Wine Festival

Chesapeake Virginia Wine Festival is an annual outdoor grand tasting held each October at Chesapeake City Park in Chesapeake, Virginia — now in its 16th year, with more than $2.5 million donated to local charities since its founding in 2009. The festival runs from noon until sunset on a single Saturday, drawing pours from 20+ Virginia wineries alongside an International Wine Village featuring selections from every continent. Presented by Atlantic Union Bank and organized entirely by an all-volunteer Rotary Club crew, 100% of ticket revenue flows directly into Rotary Community Charities supporting youth and community programs across Hampton Roads.

Chesapeake Virginia Wine Festival distinguishes itself through its charitable mission and open-air format. Founded in 2009 when Rotary members Scott Danner and Roland Davis replaced their club's spaghetti dinner with a park-lawn wine tasting, the event has grown from one tent and a handful of local vineyards into a full-day festival with two live bands performing on the main stage, chef-driven food trucks, artisan desserts, and a craft beer garden. Pours are served in real glassware, and the park grounds at 900 City Park Dr offer wide open space for guests to move freely. Themed outfits are encouraged, though casual dress is equally welcome. Parking on-site is free, and the event runs rain or shine.

Tickets and reserved seating go on sale July 1st. General admission includes unlimited tastings from participating wineries and access to the International Wine Village. Two upgrade options are available: Reserved Tables positioned closest to the main stage, and Private Chalets with dedicated servers and a curated bottle list — both suited for groups or corporate gatherings. The festival website notes that both Reserved Tables and Private Chalets sold out early the prior year, so early purchase is advisable once sales open.

Virginia Wine Country has expanded significantly as a wine region, with the Commonwealth now home to hundreds of licensed wineries producing a range of varietals including Viognier, Petit Verdot, and Norton. Chesapeake Virginia Wine Festival showcases this regional depth alongside international selections, making it a practical way to compare Virginia's wine identity with global benchmarks in a single afternoon.