Frequently Asked Questions

• What is High Street Fest?

  High Street Fest is Portsmouth’s newest signature event! A free, all-day community street festival in Olde Towne. Spanning five blocks, it showcases the very best of Portsmouth with two stages of live music, an expanded farmer’s market, more than 60 vendors and food trucks, specials from 25 local shops and restaurants, street performers, line dancing, and family-friendly fun.

• What is Sail Virginia℠ 2026 Portsmouth?

  Portsmouth is an official Affiliate Harbor to the Greater Virginia event of the national Sail250® celebration. From June 19 to 22, 2026, Portsmouth's historic waterfront will come alive with visiting Tall Ships, public ship tours, live music, family-friendly activities, and cultural programming. Whether you're visiting from across the region or right here at home, Portsmouth offers a front-row seat to this once-in-a-generation maritime event.

  The event is free and open to the public, running daily along High Street in Olde Towne Portsmouth - just a short ferry ride from the Norfolk waterfront. Tall Ships from around the world will gather throughout the Elizabeth River during the celebration, bringing maritime history and international pageantry to Hampton Roads for one of the region’s largest waterfront events in recent history.

• When and where does the festival take place?

  High Street Fest will be held from Saturday June 20 - Sunday, June 21 from 11am - 10pm in Olde Towne Portsmouth. The festival footprint runs along High Street from Water Street to Effingham Street, and down Court Street from Queen to King Streets.

• What makes this festival unique?

  Thanks to Portsmouth’s Designated Outdoor Refreshment Area, guests can grab their favorite brew, enjoy drink specials, and carry beverages outside while they explore live music, food, and shopping in the heart of Olde Towne.

• How can I become a vendor at the festival?

  We welcome local businesses, artisans, food trucks, and community organizations to showcase their products and services. Please visit our Vendors page for application details and requirements.

• Are there volunteer opportunities?

  Yes! High Street Fest depends on community support, and volunteers help with everything from event setup to guest assistance. Contact us for more information on how to get involved.

• Is there an entry fee for the festival?

  No! Admission to High Street Fest is completely free. Everyone is welcome to come out and enjoy the festivities.

• Where can I park?

  Free parking is available throughout Olde Towne. Guests may also use rideshare services, public transit, or the Elizabeth River Ferry for easy access.