We are so lucky to have so many talented artists in our community! Below are some of the posters that won our Fair Poster Contest in the past.
If you would like to submit your own poster for 2027, please check our website next winter when we release the entry criteria!
2026 Fair Poster by Sydney Smith
We are thrilled to share our 2026 Fair poster! This year’s poster, “Fair Views from the Hall,” was painted by Sydney Carminho, an ICU social worker at Tufts Medical Center in Boston.
Sydney grew up visiting the island and worked summers at Giordano’s Pizza throughout high school and college. Her poster really highlights the beauty of the Hall and our 4-H community, and we couldn’t love it more!
Congratulations Sydney! We look to celebrating with you at the 164th Annual Fair (August 13th-16th, 2026).
Read on to learn more about Sydney’s background, her poster inspiration, and her favorite things about the Fair!
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I’m feeling so excited and honored that my design was chosen for this year's Fair! I look forward to the Fair every summer and to be a bigger part of this year is really meaningful to me.
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I'm an ICU social worker living in Boston and working at Tufts Medical Center. I've been coming to the Vineyard for vacation as long as I can remember, and through high school and college I spent 10 summers living on island and working at Giordano's. Now my brother lives on island year-round, so I have a great excuse to come visit as often as I can. In my spare time I love being outdoors, paddleboarding, hiking, running, and gardening. I love making all kinds of things by hand and recently rediscovered my love for painting!
I moved to Martha’s Vineyard 16 summers ago. There was a special energy I felt when I arrived on the island. Instantly I knew it was a place I could chase my dreams and try to make it as an artist.
I painted around 60 watercolor paintings this past winter, the Fair poster being one of them. I really enjoy the winters here. It’s my favorite time to paint. I’m a night owl and usually work until 3 or 4 in the morning. I couldn’t do it without music. It’s always playing 24/7.
You can find me at the Chilmark Flea Market all summer and I have work in Copperworks Gallery in Menemsha!
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The first thing I do every year at the fair is walk through the Ag Hall to see the beautiful art, produce, and flowers. On a sunny day the light through the windows almost makes the flowers glow, I tried to capture that a little bit. And the 4-H kids are so cool - I get a kick out of seeing them show off their connection with the animals and just have fun at the Fair, so I really wanted to include that.
I had quite a few ideas. By “quite a few” I mean about 45 give or take. Haha... Anyways... I decided a rooster would be the focal point in the Fair poster. I fly fish a lot and with most of the striped bass flies I tie, rooster hackle is incorporated into them. I thought that was cool too. I have always loved sunflowers. I wanted to add some movement to the painting so I did my best to make them look like they are “dancing," welcoming everyone to come the Fair.
The Martha's Vineyard secession flag was originally going to be a cast iron frying pan filled with bacon grease that read “163rd.” But I thought there were enough circles incorporated already. So I went with the triangle faded flag thats suppose to look like its from the 70’s.
When the painting was done I spent two months looking at it everyday. I wasn't sure if I wanted to fill the background in with color or add a few other things to it. I woke up one morning, looked at it, and decided it was finished. I'm happy with the way it came out. I hope everyone enjoys it.
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Every year I get a corn dog with my family, and that has become my favorite Fair tradition/memory. But I also love running into old friends at the Fair every year, it's really a lovely place for people to gather.
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I love the energy of the Fair - excitement, joy, nostalgia, and community connection! It beautifully showcases the talent, hard work, creativity, and the community’s connection to the island in a way that has something for everyone at every age. I especially love seeing the incredible quilts, baked goods, artwork, flower arrangements, beautiful produce, and other handmade and homegrown creations on display. I think the beauty of Martha's Vineyard inspires creation, and the Fair provides a really special place for people to share their creative talents.