When I first moved closer to Southern Ontario, Hamilton wasn’t exactly on my radar as a cycling destination. Like many Canadians, I had a vague image of Hamilton as an industrial city with steel mills and a busy port. But when I actually set foot in Hamilton, I discovered something that completely changed my perception: this city is a cyclist’s dream in disguise. With the Niagara Escarpment cutting dramatically through the urban fabric, hundreds of waterfalls scattered across the region, and a growing cycling culture, Hamilton quickly became my go-to spot for both casual rides and more challenging adventures.
Cycling Hamilton is not just about burning calories or checking off kilometers on Strava; it’s about connecting with landscapes that surprise you at every turn. I remember my very first ride up the Chedoke Rail Trail — my legs were screaming, but my eyes were feasting on views of the city unfolding beneath me. That sense of “I didn’t expect this” has never left me, and every ride since then has layered new memories, new stories, and new appreciation for Hamilton’s cycling culture.
In this guide, I’ll take you through my favourite routes, the rental shops that have saved me more than once, and the hidden gems along the way. I’ll also sprinkle in practical booking advice — from reserving accommodations to securing tickets for attractions — because if you’re anything like me, you want the whole trip experience tied together neatly.
My Go-To Platforms for Planning Hamilton Trips
Before diving into the routes themselves, let me share the online platforms I rely on when organizing my cycling days in Hamilton:
- Expedia.ca — For booking accommodations close to trailheads or downtown restaurants. I’ve scored some great last-minute hotel deals here.
- Airbnb.ca — Perfect when I want to stay in a cozy home near the escarpment or get a garage space for storing my bike overnight.
- OpenTable.ca — Handy for reserving a table at restaurants in downtown Hamilton after a long ride (I can’t count the times I’ve shown up sweaty and hungry only to find the place packed).
- Viator.com — A platform I often use to book day trips, guided waterfall hikes, or even boat tours on nearby Lake Ontario when I want to mix cycling with other activities.
- FlightHub.ca — For out-of-town friends who come cycling with me, this has been a lifesaver in finding affordable flights into Hamilton (YHM) or nearby Toronto Pearson (YYZ).
With these platforms bookmarked, planning feels less stressful, and I can focus on what really matters: the ride itself.
Route One: The Hamilton Waterfront Trail
The Hamilton Waterfront Trail is where I send every newcomer first. It’s flat, it’s scenic, and it has just enough stops to keep things lively.
The Ride Itself
Starting from Bayfront Park, you can follow the trail that hugs the shoreline of Hamilton Harbour. On my last ride there, the air was thick with the smell of spring blossoms, and I couldn’t resist stopping to watch sailboats drift across the water. The entire trail stretches east and west, connecting with parts of the Great Lakes Waterfront Trail that runs across Ontario.
Points of Interest Along the Way
- Bayfront Park — This park is a hub for cyclists and families. The gentle pathways make it perfect for warming up.
- HMCS Haida National Historic Site — I once parked my bike here and spent an hour touring the historic WWII destroyer. It’s living history docked right on the waterfront. Tickets are easy to book through Parks Canada’s website or even Viator.
- Pier 8 — This is where I stop for ice cream at Hutch’s on the Bay. There’s nothing like soft serve after a sweaty summer ride.
Rental Spots Nearby
If you don’t have your own bike, Bayfront Park has a Hamilton Bike Share hub. The city’s bike-share system is surprisingly reliable. For more serious road or hybrid rentals, I recommend Velofix Hamilton — they deliver rentals straight to you, which once saved me when I realized my tire had blown just before a planned ride.
My Memories
I can still picture one fall evening when the sky turned a fierce pink over the harbour. Families were fishing along the pier, couples were strolling hand in hand, and I was pedaling slowly, just soaking it all in. That’s the kind of magic the Waterfront Trail delivers every single time.
Route Two: The Chedoke Rail Trail up the Escarpment
This is the ride that separates casual cyclists from the ones who crave a challenge. The Chedoke Rail Trail is not brutally hard, but it is a steady climb — and the reward at the top is spectacular.
The Ride Itself
The trail starts near Dundurn Street South and climbs up the escarpment along what used to be a railway bed. It’s gravel, wide, and steady. The incline tests your stamina, but it’s doable for most riders. The first time I attempted it, I had to stop halfway, sit on a bench, and catch my breath. Now, it’s a ritual ride I do when I want to clear my head.
Points of Interest Along the Way
- Scenic Park — At the top of the trail, you get sweeping views of the city and harbour. I once watched a thunderstorm roll in from here, the lightning splitting the sky over Lake Ontario.
- Chedoke Falls — A short hike from the trail brings you to one of Hamilton’s many waterfalls. It feels like stumbling into a hidden world just minutes from the bustle of downtown.
- Dundurn Castle — At the base, before you even start climbing, is Dundurn Castle. I’ve done the guided tour twice, and both times I marveled at how European it feels in the middle of Hamilton.
Rental Spots Nearby
Neworld Cycle in Burlington is my go-to for road bikes when I have friends visiting. They’re just a short drive from the trail and offer high-quality rentals. Downtown Hamilton also has smaller shops like Freewheel Cycle, which cater well to those needing a reliable hybrid.
My Memories
I’ll never forget the day I reached the top with a friend from Vancouver. He wasn’t prepared for Ontario hills (he thought we were flat prairies!), and when he saw the view, he admitted it was worth every drop of sweat. That ride turned him into a Hamilton cycling fan for life.
Route Three: The Escarpment Rail Trail to Albion Falls
This is, hands down, one of the most beautiful rides I’ve ever done in Ontario. The Escarpment Rail Trail is gentler than the Chedoke climb but longer, and it leads straight to one of Hamilton’s crown jewels: Albion Falls.
The Ride Itself
The trail runs from Corktown Park in downtown Hamilton up along the escarpment. It feels like escaping the city without ever leaving it. The greenery swallows you whole, and in spring, the air is thick with the scent of lilacs.
Points of Interest Along the Way
- Kenilworth Access Lookout — This spot gives you panoramic views of the entire city, stretching all the way to Burlington. On a clear day, you can even see the CN Tower in Toronto faintly on the horizon.
- Albion Falls — The finale. Albion Falls is a wide, cascading waterfall that looks like it belongs in a fantasy novel. I usually pack a small picnic and sit on the rocks, letting the sound of rushing water drown out the world.
- Gage Park — At the base, the trail passes near Gage Park, which has incredible gardens and a tropical greenhouse.
Rental Spots Nearby
For this route, Hamilton Bike Share hubs are scattered along the lower city, making it easy to grab a ride. If you want something sturdier, Bicycle Works in Dundas has mountain and hybrid rentals that can handle the trail’s varied surfaces.
My Memories
The last time I cycled to Albion Falls, I went alone. I arrived just as the sun was dipping behind the escarpment, painting the falls in golden light. I sat there for nearly an hour, legs aching but heart full. It felt like Hamilton had shared a secret with me — a piece of wild beauty tucked inside an urban grid.
Route Four: Dundas Valley Conservation Area Trails
This one is for the mountain bikers or gravel riders. The Dundas Valley trails are rugged, forested, and full of surprises.
The Ride Itself
There are multiple loops, from the easy Main Loop Trail to more adventurous offshoots. The forests here feel primeval — towering trees, rushing streams, and wildlife everywhere. I once had a deer leap across the trail just meters in front of me.
Points of Interest Along the Way
- Hermitage Ruins — Crumbling stone walls of a 19th-century mansion hidden deep in the woods. Cycling past it always makes me stop and imagine the lives once lived there.
- Sulphur Springs — A natural spring that still bubbles to this day. It’s a quirky little stop that connects you to the valley’s history.
- Dundas Peak — A detour worth taking. The views from here are iconic — the sweeping valley, the town of Dundas below, and forests ablaze with autumn colour.
Rental Spots Nearby
For mountain bike rentals, King Street Cycles in Dundas is my top recommendation. They’re right in town, knowledgeable, and happy to outfit both beginners and pros.
My Memories
Riding Dundas Valley in autumn is like cycling through fire — the leaves are every shade of red, orange, and gold. The air smells of damp earth, and every turn of the trail feels like stepping deeper into another world.
Food and Rest After the Ride
Cycling burns calories like nothing else, and Hamilton has a food scene that makes recovery delicious. I usually book dinner tables with OpenTable.ca, especially at spots like:
- Earth to Table: Bread Bar — Incredible pizza and fresh salads.
- The Mule — Tacos and cocktails that hit the spot after a sweaty ride.
- Born and Raised — For when I want something elevated but still hearty.
For accommodations, I often hop on Expedia.ca to grab deals at downtown hotels like the Sheraton Hamilton or book cozy lofts on Airbnb.ca near Locke Street.
Why Hamilton Cycling Keeps Calling Me Back
Every time I think I’ve “done it all” in Hamilton, another trail, another rental spot, another hidden gem pops up. This city constantly reinvents itself, showing me that it’s not just an industrial hub but a playground for cyclists. The mix of urban charm, natural beauty, and accessible rental options makes it one of the most rewarding places I’ve cycled in Canada.
And perhaps the greatest gift Hamilton has given me as a cyclist is this: a reminder that you don’t always have to travel halfway across the country to find adventure. Sometimes, it’s right here, at the foot of the escarpment, waiting with open roads, rushing waterfalls, and stories you’ll carry long after the ride is over.
