Overlook Mountain, Cooper Lake, and the trees and wildlife around Woodstock appear again and again in the Avery family’s art. Across four generations, the landscapes have remained familiar even as each artist has found a different way to depict them.

“Going Upstate: The Avery Family in Woodstock,” on view through Oct. 25 at Byrdcliffe’s Kleinert/James Gallery, is the first exhibition to bring together all four generations of artists in the family. It includes work by Milton Avery; his wife, Sally Michel Avery; their daughter, March Avery; their son-in-law, Philip Cavanaugh; their grandson, Sean Cavanaugh; and their great-granddaughter, Delilah Cavanaugh.

The exhibition also traces a relationship with Woodstock that began with summer rentals and took root in a Bearsville cottage that remains in the family.

Milton Avery’s earliest art was inspired by the American Impressionists. His style changed radically after he met art student Sally Michel in 1924. They married in 1926, and he moved from Connecticut to New York City, where the artistic ferment “woke him up,” said exhibition curator Bruce Weber. Avery began thinning his oil paints and using washes of color to suggest landscapes, people, and other subjects rather than create an illusion of reality.

To support them and give her husband time to paint, Sally worked as an illustrator, taking a job with The New York Times that lasted two decades. She energetically promoted his work, which began to appear in exhibitions and find buyers. Meanwhile, she kept making paintings of her own.

Their grandson, Sean Cavanaugh, who spent summers with his grandmother in Bearsville, said she was “such a dyed-in-the-wool fan of Milton that it was an easy choice,” one she never expressed “a shred of bitterness about.”

In 1949, Milton suffered a serious heart attack, and his doctor urged him to leave the city. The Averys went to Florida, where fellow artist Arnold Blanch told them about inexpensive rental cottages available to artists at Byrdcliffe.

Peter Whitehead and his 90-year-old mother, Jane, the widow of Byrdcliffe founder Ralph Whitehead, had abandoned the original plan for a close-knit colony of invited artists and craftspeople. Instead, they rented cottages to any artists who wished to come.

In 1950 and 1951, the Averys and their teenage daughter, March, rented the five-bedroom Eastover Cottage, built in 1902-03 as a group residence for painting instructors.

After Milton, by then a renowned artist, died of a second heart attack in 1965, Sally continued to promote and sell his paintings but could devote more time to her own. Her work, which had been close in style to her husband’s, began to diverge, with thicker applications of paint and bolder, more contrasting colors.

March Avery’s work also evolved. Growing up in a family of artists, she had begun sketching and painting as a young child, influenced by her parents’ style. In 1954, she married photographer Philip Cavanaugh, whose work also appears in the exhibition.

One Christmas, he gave her a point-and-shoot camera. She began using photographs instead of rough sketches to capture scenes she would later paint in her studio. Her use of color also set her work apart from her parents’ paintings.

“She’s very, very bold with her tones and her colors,” her son said, “more aggressive in that than anyone else in the family.”

Initially, Sean Cavanaugh resisted the family profession.

“I always made work,” he said, but “the apple wanted to fall farther from the tree.”

After graduating from college with a double major in studio art and environmental studies, he considered becoming a landscape designer. But he continued to paint.

“[A]ll of a sudden,” he said, “I started getting in shows.”

His style, too, has changed over time, becoming more detailed and realistic than his family members’ paintings.

Sean’s daughter, Delilah Cavanaugh, a student at Massachusetts College of Art and Design, created a work especially for the exhibition. Her pen-and-ink series tells a story about ancient rocks in a wooded mountain landscape. It recalls her great-grandmother’s career as an illustrator while reflecting her own love of graphic novels.

Milton and Sally had often returned to the Woodstock area, renting summer homes. In 1968, Sally bought a cottage in Bearsville, where the family frequently gathered. It was “a refuge from the city,” her grandson said, which “revitalized her physically.”

The cottage remains in the family, inspiring another generation’s work. Across their different styles and mediums, the artists return to shared subjects: the mountain, the lake, the woods, and one another.

“Going Upstate: The Avery Family in Woodstock” is on view at Byrdcliffe’s Kleinert/James Gallery, 34 Tinker St., Woodstock, through Oct. 25. Gallery hours are noon to 5 p.m. Friday through Sunday. A closing reception will be held Saturday, Oct. 17, from 3 to 5 p.m.

Margaret Tomlinson is a contributing writer. You can send her an email at reporting@theoverlooknews.com.