Other Dates
Sail Virginia℠ 2026
Location
Olde Towne Portsmouth Waterfront
Description
Sail Virginia is made up of two incredible events: the Juneteenth celebration and High St Fest, bringing together culture, community, and the spirit of Portsmouth like never before.
Juneteenth: On June 19, the Urban League of Hampton Roads, in partnership with the City of Portsmouth, presents the 5th Annual Juneteenth Freedom Day Festival – a full day of live music, food, art, and local vendors celebrating Black freedom, culture, and resilience.
Plus, don’t miss the Juneteenth Commemoration presented by History Alive, featuring walking tours, interpretive presentations, strolling characters from Portsmouth’s maritime history, and the national debut of Juneteenth the song.
High Street Festival: High Street Fest is back on June 20-22 as part of Sail Virginia℠ 2026. From waterfront tall ships to live music, vendors and family fun on High Street, it’s a full day of celebration in every direction.
Whether you’re here for the history, the music, the food, or the sails, there’s something for everyone. Portsmouth has always been a city shaped by its waterfront, and Sail Virginia is a celebration worthy of that legacy.