Toronto: Stone to Sky – Photo Walk and Tour on November 28, 2026

Welcome! “Stone to Sky” is a new photo walk and walking tour created by Mike Simpson of Tdot Shots. If you’re curious about Toronto’s architecture, the stories behind its skyline and creative ways to photograph the city, join me for an afternoon of exploration.

The idea brings together two inspirations: the ancient monument Stonehenge and the contemporary photographic phenomenon known as “Toronto Henge.” Both invite us to consider our relationship with structures, landscapes and sunlight. Why do societies build monuments of stone, metal and glass? And what makes these places so captivating to photograph?

Event information at a glance:

• Guided Photo Walk & Tour with Mike Simpson, photographer, educator, city studies enthusiast and founder of Tdot Shots
• Saturday, Nov. 28, 2026 · 3:30–5:30 pm
• $9 per person · Maximum 15 participants

Weather: The rain date is Sunday, Nov. 29, at the same time. We will move the event only if extreme weather requires it.

Stone to Sky: Toronto Architecture & Photography Walk

Exploring Verticality and Light

Architecture, history and the skyline

From cathedral spires to modern towers, our route explores how Toronto reaches for the sky. Our planned stops include St. James Cathedral and St. Lawrence Market, with views of landmarks including the CN Tower and other iconic skyscrapers and historic buildings. Together, we’ll discuss height, ambition and symbolism—and how buildings become icons. We’ll explore the Financial District and Old Town Toronto. The exact route may vary depending on weather and local conditions.

Chasing the light: our Tdot Henge experiment

As sunset approaches, we’ll explore possible alignments and compositions near St. Lawrence Market, St. James Cathedral or in the Old Town neighbourhood. Discover how scouting, PhotoPills planning and observation help us anticipate photographic opportunities. The light will guide our choices, with alternative subjects and viewpoints to explore as conditions change.

Develop your photographic eye

Try wide-angle and telephoto framing, work with silhouettes and exposure, and explore small apertures for sunstars when conditions allow. These practical exercises suit beginner and intermediate photographers. City explorers are equally welcome to enjoy the architecture, observation and discussion.

Suggested cameras and accessories

Compact, mirrorless and DSLR cameras are welcome, as are smartphones. Ultrawide and telephoto options offer additional creative possibilities. A small or full-size tripod can help steady your camera for twilight shots, but is optional.

Join us November 28 · 3:30–5:30 pm
$9 · Limited to 15 participants
Hosted by Mike Simpson / Tdot Mike

Reserve your spot using the ticket button below.
Questions? Please get in touch by email. Reach out via this site’s contact page.

Thanks, and see you on the walk!

Mike Simpson