Businesses of Savy: Martello Alley

Before and After: the transformation of Martello Alley

Once upon a time, a rundown alley transformed into a beautiful art gallery. This story, however, lacks the usual fairy godmothers and magic incantations accompanying the swish of a wand. This story involves a different albeit less glamorous magic: the power of hard work and sheer determination.

Meet David Dossett, founder of Martello Alley. His efforts are in part why Martello has grown into the thriving art gallery it is today. Naturally, I was curious to learn more about its transformation and understand what distinguishes David from other small business owners.

Before founding Martello Alley, David enjoyed moderate success as an artist, displaying his work in coffee shops and restaurants. One day, while participating in an event to paint murals on an old city wall the idea hit him– why not display his art publicly? Not only would he be adding to Kingston’s (his city’s) culture, but he would be bringing greater foot traffic and publicity to his work. David decided to test his idea out at Market Square, a heritage district constantly buzzing with city life.

Kingston, Ontario’s Market Square

He noticed that a restaurant in the square had closed off a section of its patio, so he asked if they would consider renting an outdoor piece of art for the space. The restaurant owners enthusiastically agreed, and David was able to display his work in Market Square! (He was even paid for it!) I was particularly intrigued by David’s creativity in accomplishing his goal by finding solutions for others– essentially killing two birds with one stone. The success of his painting made David realize how powerful public art can be when placed in a unique setting and this revelation surely paved the way for the development of Martello Alley.

David’s creative problem solving and careful observations were essential in the initial growth of Martello Alley. Based on his travels, he noticed that people are drawn to interesting alleyways and, as an artist, he welcomed the idea of displaying art in an alley. He approached the owner of an alley in Kingston with his idea but mentioned that parking would be an issue if artists had to load/unload their art each day. Luckily, the owner said there was a room in the alley where they could store the art overnight. David saw the space and agreed to rent it immediately! The owner threw in the alley and courtyard for free as long as David agreed to shovel it. Once again, David created another win-win situation.

“Have you ever gone into Costco looking for a jar of pickles and ended up with a canoe?” David asked. “Well, that’s me. I’m a total impulse buyer.”

Impulse buyer or not, David knew how to be scrappy while decorating his art’s new home. He bought two columns for a steal at a local antique shop and used them to embellish the gallery entrance. Ever noticed the discounted paint cans that accumulate in some far off corner of a home improvement store because they’re mismatched or off tint? David certainly has. He bought them and turned the upper brown walls into a colorful second story reminiscent of a Strasbourg waterfront. In fact, he modeled the façade after a postcard his wife sent him from Strasbourg, France.

What struck me was Martello Alley’s use of its visual aesthetics to also solve one of their greatest challenges: intimidation associated with art galleries. One day, a woman looked down the alley and asked what it was. “It’s an art gallery,” David replied.

“I hate art!” she sneered and hurried away. Although discouraged by this interaction, David came to an important realization. “I knew I would have to work through that obstacle to be successful. She, like many others, was just intimidated by the concept of an art gallery, so I focused my efforts on making the the Alley attractive, fun and intriguing by downplaying the fact that it was an art gallery.”

David emphasized how Martello strives to remove the pompous attitude often associated with art, making much effort to ensure that customers feel comfortable in the space. One way they do this is through the artists they work with. Martello’s curating committee finds artists whose work reflect the ambiance of this fun space since much of the display is geared towards their customers who are often young city goers or tourists.

Martello has steadily climbed the ranks of TripAdvisor going from 88th on Things to Do in Kingston to a coveted number 4 , begging the question: how were they able to get the word out? In addition to being listed on TripAdvisor, Martello’s colorful setting compels visitors to take pictures. David has strategically placed signs so that the name of the gallery appears in these photos. Martello also fosters a community spirit within the group of artists and the town. An artist will often announce a sale on social media and Martello Alley’s accounts will then share the post. As David describes, “That’s part of the artists’ deal. When they agree to work out of Martello Alley, the artists are expected to encourage and support each other, and we try to support them as well.”

Through its participation in local events, Martello Alley has become a vital part of the Kingston community. Locals often visit the space and share it with visitors. David says, “When I see people leading a tour as if they owned the gallery, I feel that I have accomplished something very special. It makes me proud to think that the residents of Kingston feel a kind of ownership to Martello Alley. That’s when you know that you have become an integral part of the community. That is what keeps me going.”

For our readers who immediately want to start their own business after hearing Martello’s story, David advises budding entrepreneurs to use your superpowers, to find businesses that inspire you and do what they do in a different and creative way.

If you ever find yourself in Kingston, Canada, be sure to drop by the beautiful Martello Alley or check out their website at

Are you a business interested in getting involved in the Savy community? Or maybe you just have an exciting story to share with us? Send us an email at

#staysavy everyone,

The Savy Squad ❤

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