One of our favourite questions from guests is “where should we go for a bike ride?” There are dozens of good answers around here. These are the two we give first.
South Georgian Bay is a string of small towns with genuinely good cafés between them, connected by rolling concession roads and a shoreline trail. Riding it is a reminder that days off are supposed to feel like this.
Here are the two rides we send people on from Collingwood.
Creemore, 23 km each way
A small town on the Mad River that seems purpose-built as a cycling destination. The ride there is half the reason to go: quiet concession roads, farms, bush, and hills that build steadily. There is a real climb into town at the end. What you get for it is the Niagara Escarpment on one side and open countryside on the other, and you will stop for photos more than you planned to.
Roll in and go straight to Bank Café at 179 Mill Street, in one of the town’s old bank buildings. The pastries go early for a reason, the sandwiches are made that morning, and the coffee is what you want before turning around. Their carrot cake is worth timing your ride around.

Arriving later in the day, stop at Chin Chin instead, the independent wine shop a few doors down. If beer is more your speed, Creemore Springs Brewery is one of the most recognizable breweries in the country and it is right there. Seeing where it is made is part of the trip even if you have had it a hundred times.

Thornbury, 21 km each way
For lakeside riding, this is the one. Most of the route follows the Georgian Trail, an old rail line turned into crushed gravel path running between forest, wetland and glimpses of the bay. It is flat, forgiving for recreational riders, and the kind of surface where the kilometres go by without you noticing.
In Thornbury, our first stop is almost always Good Grief Coffee Roasters on Bruce Street South. The house-made glazed doughnuts have a local following, and after a morning on the bike you will understand it immediately. We have sent a few hundred guests there and have yet to hear a complaint.

On a hot afternoon, go to Pom Pom instead. The scoops are the draw, but it is the dairy-free mango that keeps us going back. It tastes better after 21 km, which is a fact of physics we are not going to question.
Heading home, skip retracing the whole Georgian Trail. Take the farm roads through Ravenna instead: apple orchards, rolling fields and almost no traffic. It is a completely different view of the same region, and during apple season it is hard to ride more than a few kilometres without stopping.
End the day at Somewhere
After a full day on the bike, the best thing on earth is a helmet coming off and a glass of wine going in your hand.
Which is convenient, because Brooky’s, our wine bar, is on the property. Come in still in your kit if you like. We will find you something cold and something to eat, and nobody here is going to comment on the tan lines.
After that, the gardens do most of the work. Somewhere Inn Collingwood is ten rooms, built for the part of the day where you stop moving. Sink into the bed, sit outside while the light goes, and let tomorrow’s ride be tomorrow’s problem.

Plan the weekend
Somewhere Inn Collingwood is ten rooms and a wine bar, minutes from the Georgian Trail and about two hours from Toronto. Ontario’s top rated boutique hotels, with 400+ five-star reviews across Google, Expedia and TripAdvisor.
And when you check in, ask. We ride these roads. We will happily point you at another café, a better detour, or the one gravel section nobody puts on a map.
From the Front Desk is our ongoing series on the places we actually send people. Written by the team at Somewhere Inn Collingwood, who live here, ride here, and eat here. We love our backyard and can’t wait to share it with you.