Art Around The Bay

The Historic Around The Bay Race: 30 Kilometres, 31 Paintings

In a moment of questionable judgment, I took up long-distance running—not out of any great love for the sport, but as a way to connect with my dad, a lifelong marathoner. Training led me to Around the Bay, a storied 30K race in Hamilton. I ran it once and then, with great relief, retired from the sport.

But somewhere along that ambitious route, I noticed something remarkable: people. Lining sidewalks and front porches, waving signs, ringing cowbells, offering orange slices, and cheering for strangers. Not because they had to—because they wanted to.

So I came back. Not to run, but to sketch. One painting for each kilometre marker—plus the start line, for symmetry. Thirty-one glimpses into the quietly heroic, often hilarious, and deeply human tradition of showing up for each other.

The full series was eventually exhibited at the Art Gallery of Hamilton, which was lovely—and only slightly less surprising than the fact that I finished the race.

Here We Go
Kilometre 0 – The Starting Line

The gun fires, but nothing happens. At the back of the pack, we shuffle forward in the slow “pre-start drift,” thousands of runners trying not to trip over each other’s heels. Energy buzzes, nerves spark, and the temptation to sprint is strong—but this isn’t a sprint.

It’s the start of something much bigger.

Km 1 – Mission
The race begins with a crush of runners heading down James Street, legs fresh and spirits high. At the corner, Hamilton police hold the line while the city looks on—a mission in motion, both for the runners and the streets they pass through.

Km 2 – Harbour West
Just past Grandad’s Donuts (cruel), the course bends toward the harbour. The city loosens its grip, the pack starts to stretch, and the legs begin to realize this is no casual jog.

Km 3 – Eastwood Park
Here, Hamilton shows its humour with the infamous “Harbour Boobs” domes on the skyline, backed by breweries and grit. It’s a mix of fart jokes and fine art, the Hammer at its most honest, pushing runners onward.

Km 4 – Keep Moving
The first water station is chaos: cups, puddles, and determination. A cropped banner shouts “Keep Moving,” and that’s exactly the message—whether you’re seasoned or struggling, the only way is forward.

Km 5 – Double Double Time
Flat road, grey sky, and a Tim Hortons glowing like a beacon. Families cheer with coffee in hand, offering encouragement as warm and Canadian as a double-double on a cold morning.

Km 6 – Brightside Memories
Runners pass the ghosts of Brightside, a lost neighbourhood that still lingers in brick and memory. Archival figures cheer from the sidelines, blending past and present, reminding us that some communities never really leave.

Km 7 – Steel and Steam
The steel mills loom in the distance, pouring grit into the air and into the race itself. Volunteers hand out cups—some solemn, some playful—tiny rituals of care against the backdrop of industry.

Km 8 – Overpass Drift
The road rises just enough to change the view—overpasses, rooftops, and hydro towers holding up the sky. Middle miles, middle runners, steady rhythm. Below, stubborn snow clings to the city, not quite ready to let go.

Km 9 – The Curve
A simple stretch of overpass becomes something more: police halting trucks, runners streaming forward, momentum building. The bridge splits the canvas in two, a quiet rebellion against art-school rules—and maybe the moment where this whole project truly began.

Km 10 – Steam Powered Relay
Outside the old Steam Museum, the first relay exchange sparks a flurry of tags, hugs, and foil blankets. Families cheer, photographers crouch, and for a moment the race is equal parts chaos and community theatre.

Km 11 - Beachy Keen

The course swings onto Beach Boulevard, where March wind trades comfort for clarity. The lake glints through the fence, the air sharp and honest. The mills fade behind, the road opens ahead—something’s shifting. Calm, cool, a little raw—Hamilton’s idea of beach weather.

Km 12 - Tin Pan Gran

Beach Boulevard hums between lake and highway, a stubborn strip that shouldn’t exist but does. Among the cottages sits a lone woman, tin pan in hand, keeping rhythm for the runners. No fanfare—just the steady clang of tradition

Km 13 – The Chapel of Clatter

Tin Pan Alley hits full volume—cowbells, saucepans, and the eternal joggler still defying logic. Behind it all, the Beach Rescue Unit stands like a quiet chapel, steady as the noise swells around it. Fanfare, Hamilton-style: loud, loyal, and a little offbeat.

Km 14 – 582 Heroes

Through Dieppe Veterans Memorial Park, the noise softens. Flags, stone, and cold air mark a pause in the rhythm—a quiet salute to 582 Hamilton soldiers who never came home. Even the runners move differently here, carried by something deeper than breath.

Km 15 – Halfway Home

Steel grating rings beneath your shoes as the Burlington Canal Lift Bridge carries you over the water. The skyway looms, the lighthouse keeps watch, and the wind has opinions. Halfway isn’t half done—this is where every earned stride meets another dug from grit.

Km 16 – Canal Side

The lift bridge fades behind you, the Skyway arcs overhead, and Burlington unfolds—tidy, polite, but still carrying Hamilton’s grit. Eastport Drive hits with sideways wind and questions you didn’t ask. Then, salvation: a scrappy tailgate of cheers, kids, and coffee, a little jolt to keep you moving.

Km 17 – Approaching the North Shore

The road ripples beneath your feet, grey and relentless, a slow river of pavement carrying sore joints and stubborn legs. Highway stretches ahead, diesel in the air, until North Shore Boulevard appears—green and reflective—a promise of something real. Keep running.

Km 18 – Francis Road

Highway fades behind you. Burlington’s streets appear—quiet lawns, lake-scented air, birdsong, and cheering families. The pavement ripples underfoot, or maybe it’s just you. A lull before the hills—smile, breathe, keep moving.