The Gloucester Arts Festival returns next month to mark a major milestone: 10 years of bringing nationally recognized artists, live performances, and community-centered events to Virginia’s Middle Peninsula.
Presented by The Cook Foundation, the June, 2026 festival celebrates “A Decade of Art” with a full month of programming across Gloucester—from plein air painting and concerts to exhibitions and family events.
At the heart of the festival is Plein Air Week (June 5-13), when invited artists from across the country paint outdoors throughout the region, capturing Gloucester’s landscapes, waterways, and historic streets. Visitors are encouraged to explore, meet the artists, and watch works unfold on location.
Opening weekend sets the tone with three signature events: Brews, Brine & Wine on June 5 at Machicomoco State Park; Paint Main on June 6 in Gloucester’s historic Main Street district; and Symphony Under the Stars on June 6 on Main Street, presented by the Virginia Symphony Orchestra.
Beyond Plein Air Week, the festival continues throughout June with a diverse lineup of events, including: Sky Dogs at Flat Iron Crossroads on June 13, Arts at Abingdon Concert featuring Stephanie Zyzak and Keiko Sekino on June 18, Book Fair featuring Mary Shipko and William E. Johnson on June 20, Sport Star Film Screening on June 26, and Sculpture Walk, Village Arts Day, and It’s a Wrap Reception on June 27.
Together, these events reflect the festival’s mission to bring art into everyday spaces and create opportunities for the community to engage with artists and cultural experiences.
“This year’s festival is both a celebration and a reflection,” said Shandie Covington, its director. “For 10 years, the Gloucester Arts Festival has connected artists and audiences through shared experiences—and this June, we invite everyone to be part of that tradition.”
The Gloucester Arts Festival is presented by The Cook Foundation with support from Morgan Stanley.
For a full schedule of events and ticket information, visit: www.gloucesterartsfestival.com. For updates and real-time information, follow the Gloucester Arts Festival on social media.
Additional highlights during Plein Air Week include the Mathews Paint Out on June 9 and the Patron Preview Party on June 11. The culminating event will be the Plein Air Invitational Gala & Awards on June 13 at the Fine Arts Museum of Gloucester.
Artwork created during the week becomes part of the Heart of the River Collection, on view and available for purchase at the museum from June 15 through June 27.