Katherine Bradford’s Long and Winding Road — Portland Museum of Art

The departure point of the Portland Museum exhibition is “Woman Flying,” (1999), from which the exhibition has adapted its title. The painting’s central figure, like those in Bradford’s superhero series that evolved years later, can be read as a symbol of empowerment, ebullient, aloft, and ready for the freedom of flight. Alternatively, there’s something about the figure’s Muppety hands and barefootedness that suggests someone surprised to be suspended in the sky and dubious about flying, let alone saving anyone. You can’t tell if she’s rising or falling, just as you can’t tell if her swimmers, in nearby works, are lolling happily, or perhaps wading from or towards some kind of peril. Bradford identifies with the figure closely.

She describes her young adulthood mostly “in the closet” about her fierce desire not just to make art but to live “the life of an artist.” She took classes where she could, painting in her barn-turned-studio, bonded with other artists in Maine and showed some work on paper at a pizza parlor behind a Hannaford grocery store in her hometown.

“I wanted my identity to be an artist. ‘Oh, Katherine Bradford? She’s an artist!” she says, adding, “I wanted to be a player.”

But there was guilt: she’d started a family with the expectation that she would be a “political wife,” she says, to a man drawn by public service and poised for public life: Peter A. Bradford, a descendant of Massachusetts’s first governor, William Bradford, and a scion—through his mother—of several illustrious banking families (the Rothschilds, the Warburgs, the Schiffs) as well as of Abraham Abraham, the founder of the Brooklyn department store Abraham & Strauss, which became part of Macy’s.

And she got pushback: from her husband, her children and her own parents. She has often quipped that coming out as an artist in her 30s was much harder than later “coming out as queer” in her 40s. (She met Jane O’Wyatt, now her spouse, in 1990.)

In 1979, at 37, Bradford divorced and decamped from the family farm in Maine, with her 10-year-old twins in tow, to New York City. Her sister and the kids’ grandmothers all lived in the city, even as it was rounding a decade of being bleak, broken, and barreling beyond redemption, it seemed to many.

In New York, where she is still based except for summers in Maine, she painted alone when the twins were at school. In an interview she did several years ago with her son Arthur, an O. Henry Award-winning writer and Emmy-nominated filmmaker, she describes how harsh and stratified the New York art world was, and how unwelcome she felt. She commuted from Manhattan each morning by subway to a studio she eventually secured in Williamsburg—long before the Lululemons came along—where she recalls “there was one place to get food, and it was Polish food.” She mostly made her meals on a hot plate to spend every minute painting.

She was at an awkward stage of life to find a mentor, so she turned to peers and younger artists who were “ambitious and smart and seemed to have what I needed,” namely support, inspiration and guidance. She watched as some found success before she did, but “we were all cheering each other on.” Her daughter Laura, now a lawyer in New York, remembers Bradford’s friends as “grubby and penniless,” a characterization Bradford says is both true and “an authentic reaction of a child who saw her mother going in a direction that she didn’t feel [was] safe.”