Portsmouth, Virginia is proud to serve as an official Affiliate Harbor for the Sail250 Virginia, welcoming waterfront events, Tall Ships, and public ship tours from June 19–22, 2026. As part of the nationwide commemoration of the United States’ 250th anniversary, this extraordinary maritime festival will bring international vessels, cadets, and crews to the Elizabeth River—highlighted by a spectacular Parade of Sail.
From June 19–22, Portsmouth’s historic waterfront will come alive with visiting Tall Ships, interactive ship tours, live music, family-friendly activities, and vibrant cultural programming. Whether you're traveling from across the region or enjoying it close to home, Portsmouth offers a front-row seat to this once-in-a-generation event.
Learn more:https://www.sailvirginia2026portsmouth.com/
VENDOR INFO:
Vendor booths will be located along High Street in the 500–700 blocks. Spaces are available for $250 per booth, which covers all four days of the event. Each booth includes a pre-set, weighted 10' x 10' white tent. Tents are equipped with four sides that can be rolled down and secured overnight. The festival area will be monitored by 24-hour security for vendors who choose to leave materials or equipment onsite.
Spots in the Food Truck Court are available for $500 which covers all four days of the event.
Applicants are also welcome to apply to be a vendor for the 3rd Annual High Street Fest, coming back to Olde Towne on October 10, 2026.
Join us on High Street, in historic Olde Towne, Portsmouth. Olde Towne Portsmouth: Rooted in History, Alive with Energy
