Collingwood travel guide 2023: Eating, drinking and shopping

Chris and Tammy Millsap, the new hoteliers behind it the Dorchester, have had a lifelong association with Collingwood, Ont. Tammy’s father is originally from the town of Georgian Bay, and the husband-and-wife duo was born and raised nearby.

So the pair have had a front row seat to Collingwood’s transformation from a place known as a side destination for Blue Mountain skiers to a picturesque vacation spot in its own right, drawing weekend trippers (and out-of-towners looking to relocate) . “It has an elegant historic feel to it,” Chris says, while Tammy adds that the homey town is “hip and cool too.”

That’s why, when the landmark building next to Tammy’s home decor store, At Home Interiors, became available, the couple saw it as an opportunity to become a bigger part of their growing community. Dating back to 1895, the building started as a hotel – one of Collingwood’s first – before being transformed into apartments, then back into a hotel called Dorchester and then back into apartments.

When the Millsaps got their hands on it a few years ago, they reclaimed the name, restored the original brick facade, renovated and restyled the space, and last December reopened their version of the Dorchester, with 30 rooms and a retro-cool Roaring ’20s-inspired aesthetic.

When they’re not working on the hotel, you’ll find the Millsaps visiting some of their favorite local spots. Here are just some of their recommendations for your next trip to Collingwood.

For a cool hangout: Gibson & Company

As soon as you walk down the stone alley to enter, everything about Gibson & Company exudes effortless cool, as the Millsaps describe it. Part café (serving excellent coffee and light bites like avocado toast), and part wine and whiskey bar with vintage vibes, this is the place to hang out, get some work done at noon, or have an after-dinner drink, according to Tammy . “There’s a really cool, low-key vibe there,” she says.

For trendy shopping: Fashion house Metra

Tammy’s favorite place to shop in Collingwood is this adorable boutique, bustling with everything from dressy casual to full-on glam. Many pieces come from Canada from brands like I Love Tyler Madison and Montreal-based Soia & Kyo, but it also stocks labels from Europe (think Danish clothing brand Ichi). “My whole wardrobe is from Metra,” says Tammy. “I love everything about it. There is something for everyone in it.”

For exploring the art scene: Butter Gallery

If you want a weekend activity or fun date idea, look no further than Butter Gallery, the Millsaps suggest. The space specializes in showcasing contemporary pieces from artists across Canada, but is particularly geared toward Ontario creatives, including Toronto abstract landscape artist Shannon Barr and Ottawa’s Clara Kim, whose work often depicts animals. (If you’re traveling with furry friends, Butter Gallery welcomes you to visit with dogs.) It also stocks a selection of locally made jewelry. “It’s really beautiful when you walk in there,” says Tammy.

For an idyllic wine tasting experience: Georgian hills vineyards

Find this small-scale winery about 20 minutes outside of Collingwood. “They have great wine and a country charm,” says Chris of Georgian Hills Vineyards, which offers a vibrant selection of red, white, sparkling, and natural wild-fermented options, as well as crisp ciders (under the Ardiel Cider House label). The Dorchester is also partnering with the winery on an activity package, which offers hotel guests a helicopter ride to the vineyards and an on-site tasting.

For a cosy, romantic dinner: Tesoro

Walking into Tesoro, a classic Italian restaurant with a neighboring market, feels like a warm hug, say the Millsaps. For them, an evening at Tesoro guarantees a delicious meal (the lasagna and the spaghetti pomodoro with baked Sicilian meatballs are outstanding) in a relaxed environment that is also handy child-friendly if you are with the whole family. “It’s small but cosy,” Tammy describes. “The lighting is great and it’s very romantic.”

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