Paint Annapolis is on the way! Learn more about the juried artists and get yourself ready for this historic Plein air painting festival. 

We’re excited to welcome Abby Ober from St. Michaels, Maryland as a juried artist for Paint Annapolis 2024!

(Above) Abby Ober

Abby spent her youth abroad as the daughter of a foreign service officer, living in Poland, Germany, Russia, India, and Greece. She pursued an education in the Fine Arts at Rollins College in Winter Park, FL, followed by a study in Graphic Design at the Corcoran School of Art in Washington, DC.

“Moon River,” oil, by Abby Ober, 9″ x 12″

Growing up abroad with her family’s passion for fine art has influenced her journey in the arts. After a career in advertising and decorative painting in Washington, DC, Abby moved to Pennsylvania and raised two children. During this time, she returned to her love of painting, studying under various renowned Philadelphia artists.

“On Tilghman,” oil, by Abby Ober, 14″ x 14″

In 2019, Abby moved to St Michaels, MD on the Chesapeake Bay, immersing herself in various plein air events. She is dedicated to painting dramatic landscapes, seascapes, and vintage architecture capturing the distinctive light and patterns that surround her subjects. Influenced by a career in graphic design, she has recently explored the elements of abstraction in her work, both in plein air paintings and large commission work. She also teaches in various locations in MD and PA.

“Wades Point Inn,” oil, by Abby Ober, 12″ x 12″

She has participated in various plein air events including Gloucester Plein Air Invitational (2023 Best Vanishing Landscape), Wayne Plein Air (2009, 2011, 2019, 2023 Revelite Award), Winter Park Paint-Out (2020, 2021, 2022, 2023), Wekiva Paint Out (2023), and Plein Air Adkins (2023). She was recently accepted into Plein Air Easton 2024.

“Vintage Skipjack,” oil, by Abby Ober, 11″ x 14″


Abby hopes to give her viewers a new vision of nature with her expressive color and abstracted approach.

“Before Cocktails,” oil, by Abby Ober, 20″ x 10″

Learn more about Abby on her website here.

To see more of Abby and her work, check out her Instagram here.

Join Abby as one of the public artists for this year’s Paint Annapolis Plein Air Festival. Learn more paintannapolis.org

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