“Why do artists do it?” asks painter Russell Jewel. “Why do we bare our souls to the public and risk one person’s opinion?” His words capture the tension every artist feels when entering a juried event — the balance between vulnerability and ambition. But what makes a painting rise above the rest? What qualities make a viewer stop, linger, and fall in love? We turned to some of the art world’s most experienced judges, collectors, and curators to find out.
1. INTENTION
“A great painting goes beyond technical ability,” says esteemed visual artist and plein air painter Kevin Macpherson. “I need to feel the artist’s intention — the choices they made to guide the viewer through the painting, hold their attention, and convey the emotion behind it. Their reason for creating the piece must come through.”
2. THE SEVEN C’S
Veteran plein air painter Bob Upton outlines seven criteria that often guide a juror’s decision:
• COMPELLING: an irresistible visual impact that draws you in.
• CRAFTSMANSHIP: a mastery of drawing, values, paint handling, and presentation.
• COMPOSITION: a design exhibiting unity, balance, movement, and rhythm that feels intentional, not accidental.
• COLOR: harmony and relationships that make the light and atmosphere believable.
• CREATIVITY: A fresh, distinctive voice that stands out from the rest.
• CAPTURE: A truthful impression that evokes emotion.
• CHALLENGE: Evidence that the artist has overcome plein air obstacles with skill and spirit.
3. COMPOSITION
“It all comes down to composition,” says David Leadman, director of Fine Art at the Greenbrier Resort and owner of Walls Fine Art Gallery in White Sulphur Springs, West Virginia. “If the composition isn’t sound, the painting isn’t there. Be it abstract or realist, every painting comes down to shapes.”
4. FASCINATION
“Although I’ve devoted much of my life to promoting and selling art, I’ve never been compelled to create it myself,” says Susan Simpson Gallagher, owner of Simpson Gallagher Gallery in Cody, Wyoming. “That distance helps me stay objective. I just know when a piece works — when I can travel into it, rather than being stopped at first glance. Art is subjective, of course, but I trust that intuitive response.”
5. CONNECTION
For award-winning artist Stan Kurth, the standout paintings are those that make a visceral connection. “Regardless of style or subject, I look for a correlation between captivating content and mastery of the medium,” he says.
6. EMOTION
“When I’m judging an art competition, first impressions matter,” says curator and connoisseur Richard Montoux. “The emotion a piece conveys is essential — it’s what draws me in and stays with me.”
7. AUTHENTICITY
Respected watercolor artist Andy Evansen looks for paintings that showcase a medium’s true voice. For watercolor paintings, for example, he favors those “that reveal the medium’s versatility and its unique, luminous qualities — the very things that make it so beautiful.”
8. HONESTY
“In the end, it comes down to a feeling of connection,” says acclaimed plein air painter Mike Hernandez. “Beyond technical mastery or unique expression, a painting must feel honest — true to the artist’s experience.”
9. IMPACT
“Sometimes, while jurying a show, a painting just stops you in your tracks,” says California watercolorist Michael Reardon. “I know I’ve got a winner when I think, ‘I want that one on my wall.’”
10. EXPRESSION
“Judging work is an honor — but extremely difficult,” says renowned watercolorist Thomas W. Schaller. “There has to be an artistic impulse, an electric jolt of intent. Then the shapes, values, and colors must be orchestrated to create an emotional experience and a dialogue with the viewer. The best paintings make you ask questions.”
11. COMPLEXITY
For watercolorist Birgit O’Connor, a great painting balances “a strong sense of design, effective color use, creative expression, technical ability, and a level of complexity that communicates clearly with the viewer.”
12. VOICE
“I look for paintings with an identifiable voice,” says Vermont artist Charlie Hunter. “To quote Richard Schmid, great art ‘shows you what the world feels like to someone else.’ The best work captures a moment, depicts a place that resonates, or is simply beautiful — and the viewer should trust their gut about which paintings move them.”
13. BEAUTY
“First and foremost, I look for pieces that show a sense of beauty,” says artist D. Eleinne Basa. “Then I consider whether the artist has conveyed their intention and how effectively they achieved their objective.”
14. DISTINCTION
“To start, I look for paintings that stand out visually from the others,” says plein air oil painter Peggy Immel. “A strong emotional component, a unique point of view, excellent technique, and honest use of the medium are what make a painting rise above.”
15. VIRTUOSITY
“The paintings that draw me in combine virtuosity with intelligence — offering insight as well as keen perception and confident control,” says curator Mark D. Mitchell.
At plein air events, the landscape becomes the common ground that unites artists, collectors, and the community itself. Artists interpret the character of a place — its light, rhythm, and atmosphere — through their unique vision and skill, while collectors seek to take home a piece of the shared experience. This guide offers a way to deepen that connection. By understanding what makes a painting truly great, artists can express the essence of a landscape more powerfully, and collectors can recognize the qualities that give a work lasting resonance. Together, artist and collector celebrate not just the scene painted on location, but the enduring bond between place, painter, and patron that makes plein air so vital and alive.
Bonus Insights
WHY EVERY BRUSHSTROKE DESERVES RESPECT
“I take my job as a judge seriously,” says Kevin Macpherson, “because no matter an artist’s level, they’ve poured their heart and soul into the work. After more than 40 years as a professional painter, I know that growth is never linear. As artists, we evolve — sometimes moving forward, sometimes sideways, even backward — as we explore, experiment, and strive to create truly great art.”
WHY BUYING ART MATTERS
“The artists who participate in plein air events are, in many ways, small business owners,” says Charlie Hunter. “They don’t rely on grants or museum acquisitions; instead, they take a real risk — spending a week painting on spec with no guarantee of a sale.
“In general, artists are drawn to events for three main reasons, and we talk about them often to one another: 1. A well-run event; 2. Substantial prizes; 3. Strong sales. An event can survive with any two, but the best ones have all three. And of those, sales are the most important — yet that’s the one factor only the audience can control.
“When you buy a painting, you’re doing more than supporting an artist; you’re keeping the event — and the creative spirit of your town — alive. Plus, there’s nothing quite like owning an original work of art, where you can see the artist’s hand and feel the moment it was painted. The arts may not drive every local economy, but they’re vital to a community’s identity and vibrancy. A thriving arts scene attracts visitors, inspires residents, and makes a place worth living in. So if you want your town to stay lively, creative, and connected — buy a painting.”
Excerpted from “How To Drive More Sales at Plein Air Events” by Charlie Hunter.
Don’t miss your opportunity to create lifetime memories at PACE! The next Plein Air Convention & Expo is May 14-18, 2026 in The Ozarks. All training sessions are indoors on giant, high-def screens, with plein air paint-outs in the afternoons. Beginners and pros feel right at home, so register now to join us!
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Story prepared for the web by Cherie Dawn Haas, Editor of Plein Air Today
