This spring, Historic Annapolis and our partners invited artists to submit original designs for a public billboard inspired by the theme “History Marches On.”
As we celebrate America 250th birthday, we sought artwork that reflects Annapolis’s important role in our nation’s founding and the spirit that continues to shape our community today.

We received a number of creative and compelling entries, and judges chose a design by local artist Kyle Conway as the winner! His incredible design features many symbols from Annapolis’s past and present. The more you look at it, the more you discover.
His design graced the billboard facing Dock Street in downtown Annapolis all summer from from June through August, giving residents and visitors a new artistic way to experience the city’s story.
Thank you to Kyle and all the other artists who submitted designs with their creative takes on our city’s history!
About the Artist

Kyle Conway is a local artist, photographer, and illustrator with 15 years experience in forensic accident reconstruction; using art and technology to visually explain complex scenes for litigation. He has a strong passion for creating wonder and inspiring curiosity in nature, history, and science. Recently he has painted sections of the monster-filled mural at Cult Classic Brewery on Kent Island, and published his first children’s book, Inside the Human Factory.
Follow him on Instagram or check out his website: kyleconwayart.com.
Appears in History
Tagged Annapolis, AnnapolisHistory, art, history
