This June, Gloucester is again transformed into an artistic haven with the much-awaited Gloucester Arts Festival. Following the footsteps of last year’s success, 2025 promises an even more exhilarating blend of local charm and vibrant art experiences for all.
As the program grows, the Cook Foundation has expanded its team. Executive Director Elizabeth Blackney is joined by Shandie Covington Hall, the new Festival Director. David Brown, Co-Director of the Fairfield Foundation, is the 2025 festival chair. With the expansion of community engagement and partnerships, presenting sponsorship from Morgan Stanley, Plein Air Experience sponsorship from Sentara, and many local businesses, this year’s edition promises to be bigger than ever.
The festival kick-off weekend begins June 6th with the Brews, Brine, & Wine event at historic Timberneck Farm, a picturesque setting that perfectly embodies Gloucester’s natural splendor at Machicomico State Park — and it offers the first chance to meet 30 of the nation’s most accomplished Plein Air painters. The vibrant and exciting experience boasts Cappahosic Oyster Company’s prized bivalves, a festival-special ale from Gloucester Brewing Company, and exceptional barbeque by BarQ, and new this year, Copper Fox Distillery will join the festivities. RaJazz, one of the region’s finest contemporary jazz bands, will entertain the crowd.
Gloucester’s historic Main Street comes alive on June 7th with 30 invited artists and even more community artists capturing its essence during Paint Main - a “quick Paint” competition lasting just over two hours. The palpable energy of this artistic race leads up to the beloved Symphony Under the Stars Concert that evening by the Virginia Symphony Orchestra, a seamless blend of classic and contemporary music under the night sky. Gloucester’s own Liberty Dolls will open the night with a jaunty mix of patriotic and nostalgic favorites.
Each day unfolds new experiences! June 10th’s partnership with the Mathews County Bay School Community Arts Center allows for a day of art in Mathews, followed by a reception showcasing the day’s creations. On June 12th, the Patrons Preview Party, an exclusive event for ticketed Patrons, will return to Gloucester and take place on the water at Dixondale Wharf while artists paint the exquisite landscape.
The Plein Air Gala at the Fine Arts Museum of Gloucester on June 14th offers the first opportunity to see the “Heart of the River” collection created by the Plein Air artists. This year’s gala brings new glamour with a Martini Bar and an Oyster Bar by Big Island Aquaculture, and exquisite bites from Everyday Gourmet. Here, the artists showcase their finest works, vying for top honors. The Heart of the River installation will remain at the Fine Arts Museum of Gloucester through July 3rd — the first time this signature exhibition will be featured at the Museum, anchoring Gloucester’s historic Main Street.
As the festival progresses, performances at Flat Iron Crossroads will feature the Lord Nelson Band, playing original rock and roll from the foothills of Virginia’s Blue Ridge Mountains, and The English Channel. The Soma Quartet will perform for the Arts at Abingdon event on June 19th.
The celebrations peak on June 28th with the It’s A Wrap party at the Fine Arts Museum of Gloucester. The event is free and open to the public. It gives visitors and collectors a chance to view the 2025 Heart of the River Collection and purchase a painting before the exhibition closes on July 3.
This year’s Gloucester Arts Festival, with its rich array of events, stands as a testament to the community’s commitment to celebrating art in all its forms. It’s not just a series of events — it’s a vibrant journey through the artistic soul of Gloucester, bringing together local and visiting art lovers in a month-long celebration of creativity, community, and the natural beauty of the region. Produced each year by the Cook Foundation and more than 100 volunteers, it is the social and cultural soul of our home every June. Come join us!
GLOUCESTER ARTS FESTIVAL EVENT LINE UP
Friday, June 6th
Brews, Brine, & Wine
Machicomoco State Park
Friday, June 6th-28th
Traces of Transformation
A juried art show
York & Main
Saturday, June 7th
Paint Main
Tabb House Lawn
Saturday, June 7th
Symphony Under the Stars
Riverside Lawn on Main Street
Tuesday, June 10th
Mathews Paint Out
Bay School Community
Arts Center
Saturday, June 14th
Plein Air Gala
Fine Arts Museum of Gloucester
Saturday, June 14th
Flat Iron Crossroads Presents
Lord Nelson
Thursday, June 19th
Arts at Abingdon - Soma Quartet
Saturday, June 21st
Traces of Transformation Reception
York & Main
Saturday, June 21st
Flat Iron Crossroads Presents
The English Channel
Saturday, June 28th
It’s a Wrap Party
Fine Arts Museum of Gloucester
For more information, visit gloucesterartsfestival.com.