Meet our 2026 winning artist: Sadie May. Originally from Fulton, NY, Sadie is no stranger to the shores of Lake Ontario and Oswego Harborfest. She has taken her passion for art and built a thriving career designing merchandise for touring musicians. We are incredibly proud to be featuring her work this year. Read our conversation with Sadie below and check out more of her work at sadiemaysart.com.

You grew up along the shores of Lake Ontario and still call the region home - how did that shape you as a person and as an artist, and what does it mean to you to have your work representing a festival so close to home?

Sadie: Growing up in Fulton, I always looked forward to attending Harborfest. It was such an accessible and exciting event, especially when I was younger. Harborfest feels synonymous with home to me, so now that I’m fully immersed in my career as a designer specializing in event merchandise and advertising, it feels incredibly full circle to have my artwork representing Harborfest in 2026.

Your career has taken you from your roots in the region to designing merch and posters for touring musicians on a national scale. How did that journey begin, and how has your work and creative identity evolved along the way?

Sadie: I’ve always been creative, and when I look back on how that was fostered, it feels less like “when did it start?” and more like “I was never told to give it up.” I have an extremely supportive family who always encouraged my sister and me to explore our passions.

As a child, I remember being asked what we wanted to do when we grew up. My sister Amanda wanted to work with animals, and now she co-owns and operates Gentle Paws Grooming Salon in Fulton. I always said I wanted to be an artist, but I had no idea what that looked like. The path to becoming a professional creative is a little more nuanced than some other careers, but I always believed that if I kept practicing my craft and exploring ways to make a living doing what I love, I could build a stable life without giving up my dream of being an artist.

All three of my parents - my mom Bonnie, my dad Phil, and my stepdad Pete - were incredibly supportive of my art and deeply involved in the music scene. Combining those shared passions of live music and design has always felt second nature to me.

I started by making $5 posters to sell at Sterling Stage in Sterling, New York, with the blessing of the event coordinators. They were photocopies of pen-and-ink drawings. The more I created, the more I realized people beyond my family believed my art had a place in the live music scene, and that gave me the motivation to keep going.

I decided to maintain my momentum as a self-taught artist rather than attend a university for art. I don’t know what would be different if I had, but I do believe that the lived experience that I committed to has brought me to where I am today. I’ve never regretted challenging myself to learn constantly, investing into workshops and classes occasionally, rather than committing to student loans and spending my years after high school in classrooms.

Since growing up in Fulton, I’ve traveled extensively and lived in different parts of the United States, experiencing a much broader view of the world and figuring out where both my art and I fit into it. But no matter where I’ve gone, Lake Ontario has always been home. I’ve always felt that magnetic pull back to this area.

Where do you find inspiration when starting a new piece and what do you love most about this work?

Sadie: Inspiration usually comes from the location and the overall vibe. I generally work within genres like jam, rock, bluegrass, and Americana, so those environments already feel familiar to me because they’re the spaces where I’ve naturally found joy myself.

Even when I’m less familiar with an event or community, I spend time researching the area and immersing myself in its atmosphere. Harborfest was easy for me because I can vividly picture what it feels like to see the water from Flatrock or watch fireworks from Breitbeck Park. I know the beautiful chaos of the vendor areas and the smells from the food trucks.

It’s not always as easy to capture the feeling of a place I don’t personally know, but I always try to seek out firsthand experiences through YouTube videos, Reddit threads, Facebook groups, or anything else that helps me understand the spirit of a place before I begin building concepts.

When you look at your finished Harborfest poster, how do you see your artistic voice coming through in it - and how did you approach translating this year's theme, The Music that Shaped America, into something that felt genuinely yours?

Sadie: One thing I love about Harborfest is the duality between the daytime and nighttime energy of the event, and when I was developing the concept, I realized I couldn’t choose just one. I used the silhouette of the musician to embody the nighttime atmosphere, while the sunset became the central setting of the piece.

When I thought about what America looks like to me, I wanted to include recognizable iconography - flags, stars, eagles - to create an immediate sense of Americana. But I also wanted America to feel personal and familiar. I wanted the sunset and fireworks to feel immersive, like you were experiencing that moment firsthand.

“The Music that Shaped America” is such a broad theme that I knew I couldn’t represent everything within a single image, so instead I focused on creating an overall feeling rather than trying to tell every story at once.

What do you hope people feel when they see your poster, and what would you most want Harborfest attendees and the broader Oswego community to know about you and your work?

Sadie: I want people to see Harborfest the way I see it - as an annual gathering place where friends and families come together to celebrate and experience the beauty of Oswego, New York.

I’ve spent countless hours watching the glittering light reflect across Lake Ontario, and during those moments I’ve felt more peace than almost anywhere else in my life. This area is incredibly special to me, but I’ve also seen that same feeling resonate with friends from out of town when I’ve brought them here to walk the rocky shoreline and experience it themselves.

More than anything, I want people to understand one core value behind all of my poster work: when I create artwork for events - whether it’s advertising or merchandise - my intention is always to help foster a sense of community, love, and acceptance.

There’s a deep divide in society, and there probably always has been, but as I’ve grown into myself as a person, an artist, and a mother, I’ve felt increasingly compelled to help create spaces where people can connect with one another. Live music, community events, and shared experiences give people an opportunity to find common ground, even when it goes unspoken.

I may not be able to change the world, but I do hope to create moments of shared joy and mutual connection that bring people together. That has always been my goal as a poster artist.