Annapolis Through Paint and Movement
Paint Annapolis: A Week Inside the Living Gallery
The Festival
Paint Annapolis is a nationally recognized plein air festival where artists from across the country gather to paint the historic streets, waterfronts, and coastal landscapes of Annapolis. For one vibrant week, the city becomes a living gallery—painters capturing maritime beauty, shifting light, and centuries of history directly from observation. The result is a collective celebration of place, memory, and presence.
This year’s festival was a great success and an inspiring experience to be part of. The streets filled with artists, easels, and movement—paintings emerging in real time from dawn into late-night hours, some continuing until well past 4 AM as artists chased fleeting light and atmosphere.
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I almost didn’t make it in.
Just two days before the festival began, a serendipitous conversation with local Annapolis artist David Diaz changed everything. His work—rich with color and an almost cinematic sense of observation—reshaped how I see light and composition. I left that conversation seeing possibilities I hadn’t noticed before.
That meeting came through another artist, Kelsey, a local jewelry maker and fellow craftsperson, who introduced us on Maryland Avenue. What followed was nearly an hour of uninterrupted exchange—framing techniques, plein air stories from Ireland, last-minute artist hacks, and shared language around observation and craft.
Inspired, I went directly to Circle Studio and signed up. There I met volunteers and coordinators from the Maryland State Arts Council preparing the space—clearing walls for a new wave of Annapolis paintings.
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First Day: The Challenge of Time
The first day (May 31) came with a two-hour painting challenge. I quickly realized where I struggled: focus point.
I had been overwhelmed by detail—especially surrounding the beauty of the secret garden I was allowed into—and lost clarity on my central subject, a historic pine tree. Finishing that piece, I understood something essential: simplification is not loss, it is direction.
After completing my final brushstroke, I packed up, strapped my canvas to my bicycle, and rode across the Eastport Bridge to the showcase. Arriving at the pier, I was struck by what had been created across the city in just two hours. The energy of shared urgency and observation was undeniable.
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Movement, Observation, and the City
One unexpected gift of the weekend was mobility. My car troubles meant I experienced the city entirely by bike. Moving through Annapolis this way sharpened my awareness—wind, pace, light shifts, and small details that would have otherwise passed unnoticed. Whispers of Annapolis felt in first perspective.
I moved between locations freely: hills, waterfronts, neighborhoods, and trails. It became a kind of unplanned study in observation.
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Conversations in the Field
Some of the most meaningful moments came after painting—through conversations with other artists.
We talked about setups, improvisation, and the constant challenge of deciding what to include and what to leave out. Across skill levels, a shared tension emerged: focus versus abundance.
I met retired art teachers painting their own city with renewed joy, emerging artists stepping into plein air for the first time, and seasoned painters whose confidence showed in every stroke.
There was a collective sense of generosity—artists not only showing work, but sharing process.
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Sierra Fenton 
Quiet Waters and the Reception
The following day I volunteered at Quiet Waters Park, one of my favorite places in Annapolis. While there, I spent time speaking with fellow volunteers about their local ties, life journeys, and past travels. Conversations naturally drifted into stories of memory, art, and presence—some describing moments where loved ones felt close again through small signs in nature, often appearing as butterflies or dragonflies. Several even reflected on seeing similar imagery echoed in my own work, which gave the exchange an unexpected sense of continuity.
There was something grounding in hearing these overlapping stories wherever I went—like threads quietly connecting people through shared meaning and perception. It felt, at times, like a form of guidance carried through the natural world.
Later that day, I attended the festival reception, where I encountered an extraordinary range of completed works.
I met watercolor artist Rajendra KC, whose intensity of color felt almost atmospheric. I also connected with Juliya Ivanilova, a Russian watercolorist whose work captures fleeting light in everyday Annapolis scenes with remarkable sensitivity.
Another standout was Neal Hughes, whose impressionist work balances precision and luminosity—especially in his handling of water and reflection.
At the Annapolis Maritime Museum, I spent time walking through exhibits along Back Creek, where maritime history and ecological education come together through the lens of the Chesapeake Bay.
That evening, live music carried across the water as artists, families, and visitors gathered along the docks. Conversations unfolded naturally—between boaters, collectors, and artists—each moment layered with sunset light and movement on the water.
I met artists including emerging artist, Daniella Reilly, whose bold color language and expressive mark-making carried through her work, and Sierra Fenton, an oil painter whose landscapes reflect a lifetime of travel, rural memory, and observation.
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Gallery Connection:
During the festival, I connected with Jacob Goldsmith, juror and gallery director. Born in Burkina Faso and educated in Côte d’Ivoire—Jacob graduated at the top of his class in Industrial Design—Goldsmith carries a sensibility shaped across three continents and multiple disciplines. His work exists at the intersection of precision and intuition: neither purely engineering nor purely poetry, but a deliberate synthesis of both.
His practice has received institutional recognition, with works entering the permanent collection of the National Archives Museum in Washington, D.C., and an upcoming participation in his first Art Salon at the Musée du Louvre in spring 2026.
Jacob Goldsmith is also the Founder of Goldsmith & Co. Art Galleries.
Our conversation expanded into photography, composition, and the enduring influence of master artists—particularly how visual discipline translates across mediums.
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Reflection:
Paint Annapolis became more than a festival—it became a way of seeing.
Between unexpected timing, shared conversations, movement through the city, and the vulnerability of painting in public space, the experience revealed how deeply art is tied to attention. Not only in what we choose to depict, but in how we learn to perceive.
I left the week grateful for the community, the unexpected paths, and the reminder that observation itself is a practice—one that continues long after the paint dries.
I am now preparing to exhibit three new works with Goldsmith & Co.: Souls in the Sky, Wind Whisper of Hope, and Becoming. Each holds a distinct narrative, yet all are rooted in the same Annapolis journey—guided by atmosphere, memory, and movement through light.
Jacob and I also found resonance between our work in the blurred horizon line between worlds—where sky and water dissolve into one another. A shared reflection on how ancient energies feel present in these spaces, and how proximity to the sky has shifted in our lived experience, as though it is no longer distant, but something nearly within reach.
Our perspective reveal themselves while remaining present.