Cycling in York Durham Headwaters: 3 Routes to Get Better Acquainted with the Best of the Region

York Durham Headwaters if often thought of first as great road trip region for folks living in the Greater Toronto Area. However, I’m here today to talk about why YDH also needs to be on the radar of Ontario cycling enthusiasts!

Outside Pine Farms Orchard in King City in the very early spring.

Initially, I fell in love with cycling because of the way that I could separate from it all on a ride, and for cycling to act almost as a form of physical meditation.

However, I soon began to realize that cycling wasn’t just about exercise or the mental benefits that I derived from being on the saddle, it was also a brilliant way to better explore a region.

Before I knew it, I was spending full days on my bike, with stops aplenty planned throughout the day, and taking part in established routes across regions in Ontario (The Discover L & A Ride in Lennox & Addington, Stratford to Wellesley Loop and Sarnia Lambton Loop come to mind), but also helping local tourism boards establish new routes with the goal of bringing new people to new places.

I’ve said this many times before, but I do feel as if cycling offers the perfect exploration pace. When you’re walking, it’s hard to cover a ton of ground, and when you’re driving, you’re moving a little too quick to pick up the small details - the feeling of a region, if you will.

On my gravel bike, though (I ride a Trek ALR 5, for reference), I can cover ample distance, but also take it all in along the way.

Recently, I had the chance to ride three routes in York Durham Headwaters that I’d love to share with you. It’s good riding, but they’re also peppered with worthwhile stops so that you’re riding in little sprints, as opposed to one overwhelming, daunting ride. That, and you can get better acquainted with what makes this region tick by getting more familiar with YDH’s natural side, and simultaneously visiting the sites, restaurants, breweries, wineries, and shops that give this region its flavour.

Where is York Durham Headwaters?

York Durham Headwaters (or YDH) are three regions that are close enough to Toronto to only be a short drive away, but far enough away that they offer a pleasant reprieve from the hustle and bustle of Canada’s largest city.

If you’re based in and around the Toronto area, you’ll recognize many of the cities that the region is known for. Cities in Durham Region include the likes of Oshawa, Uxbridge, and the ever quaint Port Perry. York is headlined by the likes of Markham, Vaughan, King City, and Richmond Hill. And last, but certainly not least, you may recognize cities like Caledon and Orangeville from the Headwaters Region.

The cities serve as a reference point, but it’s often what you can find in between the population centres that makes this region one of my favourite in the province.

Cycling Routes to Consider in YDH

Below, I’m going to highlight some cycling routes that I feel showcase the essence of YDH, in both an urban and rural capacity. I’ll start off with three cycling routes that I’ve done recently.

The Mono to Merlot Route (Headwaters)

The Mono to Merlot route is a brainchild of this recent collaboration that I did with YDH, and it’s centred around photogenic stopping points, restaurants, and wineries - never a bad combination if you ask me.

The entire route takes about 2.5 hours for the average biker, but quick cyclists (20+ kph average) can likely tackle this in closer to 2 hours or 2 hours and 15 minutes. The Mono to Merlot route is give or take 45 kilometres in length.

I’ll run through the stops in detail, but here’s a Google Map for those who are literally sitting on the saddle, ready to get rolling! I should also note that you can add stops to the map (or remove them) to find a route that fits your desired length.

Mono Cliffs Provincial Park: I met Bri at Mono Cliffs Provincial Park before the day of riding, so that I could put the bike shoes aside for a second, and put on my hiking shoes. Mono Cliffs is located on the Bruce Trail, so you know there’s going to be no shortage of good hiking. We spent a little less than an hour there, and it was an hour well spent. Head here to see some of the trails on offer. The parking lot here is also where you can park your car, then return to it at the end of the route.
The Mono Cliffs Inn: It’s just a short ride up to the Mono Cliffs Inn, but it’s an ideal spot to grab a bite before a big ride. I’m not even going to hold back - I loved this place. So much so that I wrote a full article about why I feel the Mono Cliffs Inn is the epitome of fine country dining in this province.
Windrush Winery: A very underrated winery that has, in my humble opinion, perfected the bold red. I put together a full feature on Windrush Estate Winery over on We Explore Canada that has been popular since it was published and really dives into what makes Windrush, Windrush.
The Schitt’s Creek Motel: My gosh, who doesn’t love the magic that is Schitt’s Creek? The motel that so much of the action is centred around in the show can be easily found, especially if you want to pull over your bike for a moment before heading in or out of Goodwood, Ontario. I’d also recommend stopping into Annina’s Bakeshop & Catering, which is an iconic cycling stop in this province. Our most popular article over on Ultimate Ontario covers the Schitt’s Creek filming locations, if you’re interested!
Adamo Estate Winery: In truth, when we headed there, I found the winery a little overwhelmed with trying to find a rhythm with their newly launched menu and newly hired staff. It’s a brilliant location, they make good wine, and Adamo has no shortage of potential, but I do want to return to see how they’re faring. It’s a small batch, boutique Ontario winery where I have had good experiences in the past, but my last visit did leave me wanting more if I’m being perfectly honest.
BONUS - Maple Grove Farms: If the ride wasn’t quite enough for you, head up to Maple Grove Farm & Market in Mulmur, Ontario. It’s just down the road from Mrs. Mitchell’s restaurant, a favourite of Bri and I.

The Holland Loop (York Region)

In fairness, this is a bit of an edited version of the original, but you can find the route, more or less, that I did right here. Depending on how you want to ride, and where you want to stop, it’ll be between 50-65 kilometres, and take you 2.5-3.5 hours.

Here’s where I stopped, and what I’d recommend.

The Roost Cafe: This is one of my favourite cafes in Ontario, and I simply can’t recommend it highly enough. Anytime I’m in and around King City, I’m stopping here, and I’d encourage you to do the same. It’s a cozy neighbourhood cafe in a century home, and I couldn’t help but write a full article about The Roost Cafe for Ultimate Ontario after my experience there.
Pine Farms Orchard: This place is an institution, and they can trace their history back to 1948, when they planted their first tree. This was one of the orchards that signalled to Ontario that apple orchards could be a popular attraction in an area, and in effect, it changed Ontario tourism. Of course, I couldn’t help but put together a feature on Pine Farms Orchard as well. Hey, nobody can ever say I don’t work hard for my readers across my respective sites!
The Schomberg Pub & Patio: A historical house with a tree shaded patio in an even more historic town. Cycling, well it makes you hungry, and the Schomberg Pub & Patio sure knew what to do about that. I’d recommend eating here, and then spending some time walking up and down the main street.
Holland Marsh Winery: Holland Marsh Winery is a boutique winery in Newmarket that is demonstrating that one of Ontario’s premiere areas for growing other vegetables, the Holland Marsh, can also be used to grow grapes. I’m not necessarily sold on the interior and general vibe (though, in fairness, I didn’t spend too much time there), but I did really like their Select Cabernet Baco.
LOCALE King City: I changed out of my biking gear, put on some less tight clothes, and Bri and I had a lovely date night here. They’ve got local beers on tap, and an excellent, eclectic menu. We had the Spaghetti Frutti Di Mare and the Branzino (seared sea bass fillets), both of which were exceptional.

Other spots you could include would be Grackle Coffee (Schomberg), Round the Bend Farms (Kettleby), and if you’re looking to extend the ride after my last stop here, head to Rosie’s Bar (Aurora).

Scugog Country Cruise (Durham)

In exploring Durham by bike, we used the Scugog Country Cruise (a 28 km or so route) as a guide, then built some extra stops around it.

White Feather Country Store: Welcome to Durham Region’s largest country store! They like to say that “White Feather has everything from fresh apple fritters to home decor!” Personally, I was (not surprisingly) enamoured by the sheer scope of their baked goods section. I wanted to buy literally everything. So, word of warning - arrive with an appetite. It’d be a mistake not to try one of their famous apple fritters, by the way!
Ocala Winery: Ocala Winery is Durham Region’s only grape grower, plus they’ve got a 100 year old apple orchard on the property. In all, they make over 30 varieties of wines. You’ll have some more classic variations that are grape based, but they also dapple very heavily into fruit wines if that’s your thing.
Willowtree Farm: They’ve been family owned and operated since 1969, and this is a place that does this the right way. The McKay family works about 600 acres to bring over 30 different fruits and vegetables directly from their fields into your shopping bag. They also have ample antibiotic and hormone free meat available as well. This is a bit of a hidden gem as far as I’m concerned. We ended up with a bunch of stuff to bring home with us!
Marwan’s Global Bistro: This Port Perry institution is a place that Bri and I usually stop every time we’re rolling through the town. It’s right on the main street in the downtown core, and they offer internationally inspired food (some of the best butter chicken in rural Ontario, without question), as well as a nice selection of local beers on tap. If you’re hungry, I’d recommend starting with their Old Flame and Cheddar Cheese Soup.
Explore Port Perry: This isn’t necessarily a “stop” on the cycling route as much as a recommendation that after you dine at Marwan’s, you take a moment to explore Port Perry. I actually put together a guide on Port Perry to help people get the most out of their visits to one of Ontario’s prettiest towns.
The Scugog Shores Museum Village: This museum showcases what life was like in Scugog from the mid to late 1800s. For reference, they typically open for the season in late May, as it’s an outdoor museum in many respects. That being said, if you’re cycling in York Durham Headwaters, there’s a decent chance it’s not winter anyhow and the Scugog Shores Museum Village will be open.

If you want to lengthen or customize your route a little bit, you can tack a visit to Linton’s Farm Market (Oshawa) onto the tail-end of this.

More Cycling Options in York Durham Headwaters

First and foremost, you should know that YDH is continuing to build out a cycling section on their website as they continue to become known as an Ontario cycling destination. You can find that here.

Here are a few spots that you might want to consider that are mentioned:

Cold Creek Conservation Area ( Nobleton, Ontario - 6.6 kilometres of trails)
Durham East Cross Forest Conservation Area (Nestleton Station, Ontario - 7 kilometres of trails)
Kortright Centre for Conservation (Vaughan, Ontario - 16 kilometres of trails)
Albion Hills Conservation Area (Caledon, Ontario - over 50 kilometres of cycling terrain to cover)
Lynde Shores Waterfront Trail (Whitby, Ontario - about 12 kilometres of trails)
Elora Cataract Trail (Between the towns of Elora and Forks of the Credit - 47 kilometres of trails)
Bartley Smith Greenway (Vaughan, Ontario - 15 kilometres)
Caledon Trailway (Spanning Caledon from Terra Cotta to Palgrave - about 34 kilometres)
Michael Starr Trail (Oshawa, Ontario - 5 kilometre trail)
If you’re looking for something a little larger, the Terra Cotta Loop is 134 kilometres in length. You can check it out here, and there’s also some info about the Creemore Gravel Trail and the Oro-Medonte Rail Trail.

That’s a wrap on my coverage of some premiere cycling options in York Durham Headwaters. As always, I hope the time I’ve put into creating this content pays off in spades for you, and encourages you to get out, explore, and form a greater appreciation and attachment for this region.

We want to humbly thank York Durham Headwaters for hosting us as media. All opinions are completely our own.

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