Around this time every year, someone leans on the front desk, looks out at the grey sky and asks, "so what do people actually do here in November?"
Honestly? Some of our favourite things. The leaves are down, the ski hills are still waiting on snow, and town gets quiet in the nicest way. The patios are stacked away, the restaurants get cozy, and you can walk into most places without a wait. It's the season locals keep a little bit to themselves.
So here's what we tell people when they ask. Consider it the late fall list.
Coffee first, then the water
Every good day here starts the same way: a coffee and a walk. Gibson & Company is about four minutes from our door, and if you want a pastry with it, Espresso Post is right around the corner.
Photo: Espresso Post
Take it down to the bay. The waterfront trail runs right along Georgian Bay, and if you keep going you'll end up at the little lighthouse at Sunset Point Park , about fifteen minutes on foot. The bay goes steel-blue this time of year and the wind has opinions, so bring a hat. You'll have most of it to yourself, and the coffee tastes better for it.
Photo: Roman Zelvenschi
When it rains (and it will)
Late fall weather keeps everybody humble, so we always have a rainy-day plan ready.
The Collingwood Museum is four minutes away in the old 1873 train station, and it's where you'll learn this town used to build ships, big ones. It's open Tuesday to Saturday, and it's a good hour.
After that, wander downtown. Pop into Little Brothers for a vintage jacket you didn't know you needed, then Bishop Consignment if you're feeling lucky on the designer front. Our last stop is always Dags & Willow . They have the biggest artisan cheese selection in the area, and a board from there plus a bottle from downstairs is our idea of a perfect room-service night.
Photo: Collingwood Downtown BIA
Photo: Dags & Willow
Saturday, take the drive south
If you only leave town once, make it Creemore on a Saturday. It's about thirty minutes, and the farmers' market is on at Station on the Green from 10 to 2. Grab something from the pastry case at YF Patissier Chocolatier, walk Mill Street, and finish at Chin Chin , the tiny wine bar and shop a sommelier and his wife opened a couple of years ago. Sit by the stove. Stay for one more.
Photo: YF Patissier Chocolatier
Photo: Chin Chin
On the way home, pull over in Nottawa. Nottawa General lives in the old red-brick general store, and the Nottawa Cottage Bookstore is in the little cottage out back. We've never once left without a book.
Photo: Nottawa General
And if you've timed it right, swing by Devil's Glen on the way back. The lookout over the Mad River valley turns gold right before sunset, which after the clocks change on November 1 is around five.
Photo: Mathias Buytaert
A night out (or two)
This is the season this town comes out to the theatre. The Gayety is a short walk up Hurontario, and the fall lineup leans hard into tribute nights. Grace 2 plays the Tragically Hip on October 23, and Sinatra in Love with Jeff Madden is on November 8. Fleetwood Mac Mania does a matinee and an evening show on November 7.
Over at the Simcoe Street Theatre, Gaslight's If These Walls Could Talk runs October 24 to 30: four short plays written by locals about the old buildings and the people in them. Fitting, since you'll be sleeping in one.
Here for Halloween? The Black Harvest Festival takes over downtown on October 31 from 11 to 3, and Rocky Horror plays the Gayety that night. Costumes very much encouraged. The next afternoon, head to the Pumpkin Drop at the Nottawa fire station, which is exactly as fun as it sounds.
A few more we've got circled: Elliott BROOD at the Avening Community Centre near Creemore on November 6 and 7, and the Christmas Craft Show in Stayner on November 7 if you want a head start on gifts.
Where we'd eat
When guests ask where to book, these are the answers we give first.
Lore is the sister restaurant to The Pine in Creemore, and it's six minutes from our door. It's the dinner you dress up a little for. Bocado is also about six minutes away, with seasonal, Spanish-inspired plates and a very good cocktail list. For a slow lunch, Poppy's is the French bistro of your dreams.
Photo: Lore
Photo: Bocado Collingwood
Worth the five-minute drive: The Judge , a sixteen-seat pasta bar where chef Jonathan Gushue makes everything by hand. Book ahead. Seriously.
Photo: Pamela
Nightcap at Bar Gondola , six minutes away, if you're not ready to call it. Text us before you go and we'll help you land a table at any of these.
And then, come home to the heat
Here's the real secret of late fall: it's the best season for the sauna. Ours runs from 8am to 9pm, and there's nothing like stepping out of the heat into air cold enough to see your breath, then doing it all again.
Next door, our movement and wellness partner Everlove runs yoga, pilates, strength and recovery classes all day. Add unlimited classes to your stay for $60 per person, or book a massage for $120. Your legs will thank you after all that walking.
Then come down to Brooky's , our lobby wine bar, for a glass before dinner or after. On Sundays every bottle is half price, which, if you ask us, is the best argument for a Sunday night stay.
Plan the weekend
Somewhere Inn Collingwood is ten rooms and a wine bar in historic downtown Collingwood, a short walk from everything on this list and about two hours from Toronto.
And when you check in, ask. We live here. We'll happily tell you which show is worth it, which table to book, and where the bay looks best on a grey afternoon.
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, walk these streets, and eat here. We love our backyard and can't wait to share it with you.
Come see it for yourself.
A thermal cycle, Brooky’s Wine Bar and ten rooms in historic downtown Collingwood.
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