Wendy Cross’ Not a Pretty Picture: America in the 21st Century, on display starting this week at Brattleboro’s Gallery in the Woods, is full of surprises. Not that it’s whimsical, though there are such elements in several of her canvases. The unexpected moments are, more than anything, the result of juxtapositions.

The skies in her paintings often dominate, and range from pastel-hued cartoons to (more often) exquisitely rendered stretches of near photorealism. Those skies, from lovely sunsets to looming tempests, sometimes offer stout contrast to goings-on underneath. There, figures crafted in a soft-edged version of outsider awkwardness go about their business amid the rubble of the modern depression.

Such contrasting styles don’t seem at odds, even if perhaps they should. Instead, the lovely skies seem to cap scenes of timeworn despair and pathos with the mute beauty of nature. The more closely you look, the clearer it is that Cross is both a highly skilled craftswoman and a devoted chronicler of contemporary economic woes.

In a recent interview, I asked Cross if her work is intentionally political. “I don’t know if that’s exactly what I set out to do, but it always seems to end up that way,” says Cross. “I get ideas—they gnaw at me, and I have to paint them. I don’t really want to hit people over the head or anything, but I guess some of my paintings could get interpreted that way.”

Part of the equation is simply what her eye is drawn to when she looks at a landscape. “I’ve always been attracted to the darker elements of landscapes,” Cross says. “I painted landscapes for over 20 years. Even before I turned to the subject of the poor economy, I found that even back then my landscapes had details like trash or abandoned buildings. I’ve always been drawn to that. After 9/11 and 30 years of our decline, that’s really what attracts me as an artist.”

About those remarkable skies Cross says, “I guess I just really like beautiful skies!”

The contrasting style of her figures came from her art school fascination with primitivism. “You go to art school and you find out there are all these kind of rules,” she says. “You have people trying to teach classical painting, and I understand [why they teach] that, but I didn’t want to paint like everyone else.

“[Outsider art] is so free-form, and people don’t think about the rules. I find even now when I’m working, if I get bogged down with details and overwhelmed with the painting, I just have to sit back and relax and let it happen.”

Cross grew up in Connecticut, but attended art school in Ohio. That, she explains, changed her perspective. “It was an eye-opening experience. I came from a pretty affluent area,” says Cross. “I think everyone thinks poor people only live in urban areas. You get to Appalachia and you can’t believe how poor people are. Your values kind of change.”

Cross’ open-eyed approach extends, in this exhibition, to the Valley. She explains that she and her partner, upon moving to northern Connecticut, explored that area and the Valley extensively. When, on one trip, they decided to take the exit to Holyoke, she says she discovered a very different setting than the pleasant rural New England vibe she’d come to expect here.

“I found Holyoke overwhelming,” she says. “We turned down this street and this gentleman was just clinging to this light pole. It was a surreal scene.”

That scene became a central part of the canvas called “Holyoke (This is a True Story)” (which is pictured). Most of Cross’ canvases are less cluttered, their perspectives more natural. This one piles up buildings without regard for a common vanishing point or even relationship to the ground underneath. “The sort of montage comes from the overwhelming feeling it gave me,” explains Cross. “All the deserted factories—how does a city get this way, and what can you do about it?”

Cross takes the same question to other settings in her work, creating scenes at once bleak and cartoonish. They may not offer answers, but they pose their questions in a sophisticated way that’s worth more than a passing glance.

Not a Pretty Picture: America in the 21st Century: Recent Paintings by Wendy Cross: reception Jan. 6, 5:30-8:30 p.m.; exhibition: Jan. 6-Feb. 26, Gallery in the Woods, 145 Main St., Brattleboro, (802) 257-4777, www.galleryinthewoods.com.