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.

A vibrant painting of a city street during a marathon with numerous runners in colorful athletic attire. The scene features tall buildings, city traffic lights, and a crowd of spectators in the background, capturing a lively urban atmosphere.

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.

Painting of people standing in line on a city street, with trees, buildings, a traffic light, and police officers in bright vests.

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.

A watercolor painting showing a group of people participating in a running event or race in an urban area. The scene includes a sidewalk, street, and green space with trees and fences, with some participants wearing colorful athletic clothing.

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.

A city park scene with a large leafless tree in the foreground and a bicycle leaning against it. In the background, a group of people are walking along a path, with some holding hands or backpacks. Behind them are industrial buildings, including a warehouse with a sign that says "BERMING." The sky is depicted with swirling clouds, and the overall style of the painting is impressionistic with bold brushstrokes and vibrant colors.

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.

A marathon race on a wet road on a rainy day with runners and spectators, some with umbrellas, and greenery and buildings in the background.

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.

Painting of a city street scene on a rainy day, showing people walking with umbrellas, traffic cones, traffic lights, power lines, and billboard advertisements.

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.

A painting of a city street at a crosswalk with pedestrians, traffic lights, a bus, a police car, and a gas station in the background. The sky is colorful with swirling blue and gray clouds.

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.

Colorful painting of people setting up about 10 tables and tents in a parking lot with an industrial background, cloudy sky, and some cars parked.

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.

A painting of a group of runners participating in a race on an elevated road with urban buildings and shops in the background, and cloudy sky overhead.

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.

Painting of a busy elevated sidewalk with people jogging and walking, overlooking a cityscape with roads, cars, and power lines.

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.

Painting of a park scene with people running and walking, some wearing relay race bibs, set against a cloudy sky with the sun setting and a clock showing 57:40.

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.

A painted depiction of a street scene with a police car, pedestrians, houses, large electrical towers, and trees against a colorful sky. Street signs indicate the intersection of Beach Blvd.

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.

A painting of a neighborhood scene with people running and walking near a park, including a woman sitting on a green bench, and houses with bare trees in the background.

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

A colorful painting of a street scene with houses, trees, and people walking and sitting outside. Some power lines are visible overhead.

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.

A watercolor painting of a rainy day community scene showing runners in a race, spectators, a large leafless tree, tents, a house, and flagpoles with flags in the background.

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.

Painting of a bridge over water with a park in the foreground, people jogging and walking along a pathway, the Canada tower structure, and a partly cloudy sky.

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.

A colorful painting of a city scene under an overpass, with pedestrians, children, and dogs on a grassy field, trees with orange and pink leaves, and cars on the street.

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.

Painting of a city street scene with pedestrians running on a flooded road, traffic cones, highway signs, buildings, and trees in the background.

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.

A colorful painting of a winter scene in a neighborhood with snow-covered streets and leafless trees. People are walking, and there is a police officer in a reflective jacket. Houses and cars are visible on the sides, with a water body and a bridge in the background under a bright sky.

Km 18 – North Shore Blvd. at 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.

An impressionist-style painting of a street scene in a neighborhood with people walking and jogging, trees, utility poles, stop signs, and a blue house in the background.

Km 19 - North Shore Blvd. at Edgewater Crescent
Runners curve inland near the golf course, beneath a restless spring sky. The scene captures a quiet stretch of the “Around the Bay” course where rhythm and reflection meet.

An impressionistic painting of a park scene with people walking and running on a winding path surrounded by trees and greenery. Bright colors and bold brushstrokes depict a lively outdoor environment.

Km 20 – Peaceful Neighbours

Fresh relay runners slip in with enviable bounce, the rest of us carrying twenty kilometres of decisions. The neighbourhood pretends nothing odd is happening: tidy lawns, polite trees, a street trying to stay serene as colour and motion thread through it. A brief, quiet breath before the tilt of the road and the real work waiting at Valley Inn.