Walking through downtown Annapolis in summer, you don’t usually have to dodge professional oil painters with easels set up around the streets. But during Paint Annapolis, a plein air painting festival held this month, you might have encountered just that. For a week in early June, artists worked outside to capture the charms of the bayside town, setting up their easels on street corners, docks, and cobbled sidewalks. The breeze was just right. The boats floated gently on the Bay. With acrylics, oils, and watercolors, these painters caught the magic of a Chesapeake summer.
The en plein air approach—French for “in full air”—is a method of painting done entirely outdoors. The Chesapeake Bay waterfront offers plentiful subjects to paint, so it’s no wonder that the national plein air festival circuit has many stops in the Bay region. Along with Annapolis, several more towns will welcome artists later this summer, including Easton in July and Ocean City in August.
“Plein air painting in the Chesapeake Bay region dates back to the 19th century when artists sought to capture the fleeting beauty of the Eastern Shore’s marshes, historic towns, and working waterfronts,” says Plein Air Easton event coordinator Marie Nuthall.
In Annapolis, I spoke with several local artists working to celebrate the scenes of their Chesapeake home. I stood next to Freeman Dodsworth in the sun as he painted a scene of cellar stairs on Prince George Street in Annapolis. He shaded himself with a hat and umbrella. Between daubs of red bricks and yellow flowers, he told me how he got into plein air. “I refer to it as my third career,” he said. After 25 years in the Navy and 15 more as a Navy contractor, he discovered the joys of painting— by teaching himself with YouTube tutorials. Six years later, he’s on the festival circuit, has work in multiple galleries, and is a juried artist in the prestigious Easton festival.
He lives in Calvert County. “Having lived here for so long,” he said, “the Chesapeake Bay becomes your muse. Boats, clouds, water, old boats, old buildings, marinas. Anything that’s in the watershed is of interest to me.” He’s painted in all kinds of Mid-Atlantic weather, too: last winter, in Waterford, Virginia, he painted a watermill in 19-degree cold. “That was my coldest day yet,” he recalled. “It’s not meant to be heroic. It’s just that on days like that, the light is a certain way, and it’s got a special feel to it—you know. I like to catch those days when I can.”
“The Chesapeake has always been a part of my life,” said Lynn Lewis, a juried painter in Annapolis and Easton. She recalls crossing the Bay Bridge as a kid, starting her marriage in a white cottage in Deale, Anne Arundel County, and swimming in the Great Chesapeake Bay Swim. “This area always holds precious memories, while also giving me continued inspiration.”
Here are some of the inspiring plein air paintings born of real life moments around the Bay:
The Annapolis festival was livelier than you might expect. It kicked off with an event called Dueling Brushes, in which artists had two hours downtown to make a piece from start to finish. The “Paint The Bay” reception at the Bay Ridge Marina allowed juried painters to display their work as they sipped wine with potential buyers. During a Dinner Under the Stars event on West Street, they painted nighttime scenes, called “nocturnes,” setting up their easels near packed streetside tables to the music of a live band.
The Easton festival, from July 11-20, will be even bigger. “Easton is like the superbowl of plein air festivals,” one artist told me at a party in Annapolis. With 58 juried artists, and hundreds more in the fast-paced Quick Draw event, the festival—the most prestigious in the country—draws crowds from all over the map. Artists will paint from life in some of the loveliest spots of Talbot County, including Oxford, St. Michaels, and Tilghman Island.
The Easton festival celebrates the natural beauty of the Chesapeake by partnering with Eastern Shore Land Conservancy (ESLC). “Prize-winning alumni artists were invited to paint protected properties through a special Alumni Invitational Exhibit and Sale that will take place during Plein Air Easton this July,” Marie Nuthall says. “Plein Air Easton has always been a celebration of place, and this collaboration is an enduring acknowledgement of the beauty of Maryland’s Eastern Shore.” The artists’ finished works will serve as visual tributes to the region’s protected landscapes, reinforcing the importance of conservation efforts for future generations.
Plein air festivals are about more than just painting: they‘re for the public. “Our mission is to create connections in the community through art, and this is the best way to do that,” says Patrice Drago, editorial director for the Maryland Federation of Art (MFA), which hosted the Annapolis festival. “It’s a way to learn about how artists are very productive members of commerce. They’re all individual and self-employed. They’re very much a part of the industry and economy.”
Whether you’re a buyer, an artist, or an observer, a Chesapeake plein air festival is a great way to deepen your love for Bay towns or to discover them for the first time. Easton’s festival will be from July 11-21. The Harford Plein Air Painting Festival, on the upper Bay, goes from July 1 to September 12. Ocean City is hosting one from August 13-17, and Worcester County from September 14-19 in Berlin, Maryland.
Stewart White, a watercolor artist from DC I met painting on State Circle in Annapolis, told me these festivals are for everybody, even non-painters. “When they’re painting and you’re looking over their shoulder, you’re engaged in the process as well,” he said. “And that’s the artistic experience. It’s the seeing of something.”
