Gloucester Arts Festival

05/31/2026

“Things You’ll Start Seeing Around Gloucester”

05/29/2026

🎨 Paint Main returns to downtown Gloucester on Saturday, June 5th as part of Gloucester Arts Festival Opening Weekend.

Whether you come to watch artists at work, explore downtown, or simply enjoy the atmosphere, Paint Main is one of the Festival’s favorite traditions each year.

Join us in the heart of Gloucester for a day filled with art and community.

05/27/2026

🍺🦪🍷 Brews, Brine & Wine is almost here — and Opening Weekend starts on the waterfront.

Fresh oysters. Craft beer. Wine. Live music. Sunset views at Timberneck Farm.

Kick off the Gloucester Arts Festival with one of the Festival’s favorite traditions before tickets are gone.

🎟️ Get your tickets now Gloucester Arts Festival

05/26/2026

Join us this June as we celebrate a Decade of Art!!

June in Gloucester, Virginia means summer fun is here!

Summer kicks off in a big way in Gloucester with the return of the Gloucester Summer Kick-Off Carnival at the Old Page Grounds for two weekends packed with fun.

We’re also celebrating the 10th Annual Gloucester Arts Festival, showcasing creativity, culture, and community all month long!

And this summer marks the beginning of exciting America250 celebrations, including Visit Gloucester joining neighboring York County, Virginia as a special guest for Sail250 presented by the National Park Service.

From festivals and live entertainment to summer traditions and historic celebrations, June is packed with reasons to explore Gloucester!

05/22/2026

The Plein Air Invitational would not be possible without the generous support of our Award Sponsors.

Their support helps recognize the incredible artists who travel to Gloucester each June and celebrates the creativity, talent, and spirit of plein air painting throughout our community.

Thank you for supporting the artists and helping make Plein Air Week possible. 🎨

05/20/2026

A special thank you to the event sponsors helping bring a month of art, music, community, and creativity to Gloucester this June. 🎨 🎸🖼️

Your support helps make the Gloucester Arts Festival possible!

05/18/2026

🎶 As the sun sets over Main Street, the music begins.

Symphony Under the Stars returns this June for a special 20th anniversary performance with the Virginia Symphony Orchestra as part of Gloucester Arts Festival 2026.

For two decades, this evening has brought the community together through music, summer nights, and unforgettable moments in the heart of Gloucester.

Bring a chair. Bring your people. We’ll see you under the stars.

📅 Saturday, June 6
📍 Walter Reed Way & Main Street, Gloucester

05/17/2026

This week, many of the artists participating in the Gloucester Arts Festival Plein Air Invitational were sharing their work and teaching at the Plein Air Convention & Expo — one of the largest gatherings of plein air artists in the country.

We’re proud to welcome these talented artists to Gloucester this June as they paint throughout the county during Plein Air Week. Keep an eye out for easels popping up across Gloucester, June 5–13. 🎨

05/16/2026

Some places just feel different during Festival season.

As June approaches, Gloucester begins to fill with art, music, conversation, and familiar traditions that bring the community together year after year.

From gallery strolls and waterfront evenings to Main Street gatherings and unexpected moments around town, the Gloucester Arts Festival is almost here.

📅 June 5–27, 2026