The Most Romantic Towns in Ontario

These five Ontario real estate markets are sure to get you and your significant other in the mood for love.   

By Josh Sherman | 4 minute read

From snowy mountain retreats to rolling vineyards, the most romantic towns in Ontario have something for everyone.

Valentine’s Day is just around the corner, and in anticipation of the universal celebration of romance, Wahi spoke to local Realtors about some of the most romantic towns in Ontario.

“It depends on what your definition of romantic is, but I view it as a great activity during the day and a glass of wine and a fire going in the fireplace in the evening,” Shawn Woof sales representative and senior vice president at Sotheby’s International Realty Canada, tells Wahi.

The following five Ontario towns are the perfect setting for that and a whole lot more. 

1. The Blue Mountains: “A Getaway Place”

The town: The area in and around the Blue Mountains isn’t just a ski destination (though it does boast north of 40 ski and snowboard trails). Located on the southern shores of Georgian Bay, the broader region is brimming with spas, resorts, beaches, and more. “There are definitely some romantic places,” says Janet Piotrowski, a Broker at Royal LePage Locations North. “Scandinave Spa would be a great one — You can get a couples massage and then go and use the water facilities,” she says.

Just 10 minutes from the slopes, the town of Collingwood is bustling year-round. “There’s some great little boutique-style hotels and some really nice restaurants,” says Piotrowski, who wrote A Foodie’s Guide to Celebrating Special Occasions in South Georgian Bay. “This is a getaway place — and its year-round.”

The market: From historic red-brick homes in downtown Collingwood’s heritage conservation district and large country estates closer to the mountains, to waterfront condos, the area boasts properties of all kinds — and for all kinds of buyers, too. “[There are] condos near Blue Mountain Village that you’re allowed to rent out on a short-term basis for people who are looking for investment properties,” Piotrowski tells Wahi.

Be prepared to pay a premium in the Blue Mountains proper. The median price of a home in the Blue Mountains was pushing a million dollars ($980,000) in January, according to Wahi’s analysis of data from Information Technology Systems Ontario.

2. Muskoka: Cottage Country

The town: “The romanticism of the area isn’t based in a town,” says Woof. “It’s based in what you can do,” he continues. On that front, the District Municipality of Muskoka, where he lives and works and which encompasses what most Ontarians think of as Cottage Country, impresses. From golf, boating, and al fresco dining in the summer, to snowmobiling, skiing, skating, and ice fishing in the winter, Muskoka is a romantic backdrop for near-endless activities. “There’s much more activity in the summer, but if you’re looking for a quiet winter wonderland getaway, with that romantic twist — or family-focused — Muskoka’s a great option, especially if you’re a winter-lover,” Woof notes.

In the Town of Bracebridge, known colloquially as Muskoka’s Downtown, couples can wine and dine as well as stock up on supplies for a cottage getaway. “There’s definitely great restaurants and great shopping year-round — and all of your cottage essentials can be had in these towns,” says Woof, who also highlights Huntsville, the largest town in the region with a population in excess of 20,000.

The market: Muskoka is synonymous with luxury listings and celebrity sightings, and properties can get quite pricey. However, you don’t need to be part of the 1% to own a piece of Cottage Country. “There is a misconception that Muskoka is only for the ultra-rich,” says Woof, who acknowledges that there are some stunning multi-million-dollar cottages on Lake Joseph, Lake Rosseau, and Lake Muskoka, or the Big 3. “If you’re open to a smaller lake, there are more modest cottages in the $1 million range, and if you’re open to travelling a little bit farther — outside of a two-hour-driving window from Toronto — there are some areas which offer tremendous value and a similar cottage experience.” 

3. The Distillery District: “A Little Village” in the City

The town: OK, Toronto’s Distillery District technically isn’t a town — but the neighbourhood’s got all the charm of one. “It’s kind of like a little village,” says Jo Citro, a Realtor at Royal LePage Terrequity Brokerage who is representing a penthouse listing in the neighbourhood.

Couples desiring a romantic night on the town have no shortage of options in the Distillery District, once home to a large whiskey producer, whose red-brick facilities still stand today. “Tt’s got the old and new in it — a really great combination of both,” Citro tells Wahi. “If you love art and great food… and bakeries… and coffee, you couldn’t ask for more.”

The market: Those looking to buy in the area can expect to find prices slightly more affordable than the downtown core (by about 5% to 10%, Citro estimates) without sacrificing access to amenities. “It’s good value, still,” says Citro, who expects the area will only become more attractive as the nearby Portlands are developed. “The portlands are going to bring a great amount of services, schools, expanded transportation, et cetera to the whole area.”

4. Niagara-on-the-Lake: Wine Country

The town: Ask Andrew Perrie, a Realtor and CEO of The Fine Estates Team, about the romantic attractions in Niagara-on-the-Lake, and doesn’t know where to begin when asked “You’ve got the wineries, of course,” he begins. “It’s about finding those wineries that offer such a one-on-one experience, such as Perridiso Estate Winery,” he suggests. The estate winery is based out of a beautiful home set on 30 acres of rolling vineyards, he says, and offers an intimate experience. “It really offers that one-on-one attention where you get to actually sit with the winemaker as he’s tasting it with you,” he says. “A lot of people get married there.”

Meanwhile, over on Queen Street, the community’s main strip, there’s almost too much to take in. “It’s the most charming downtown area you’ll probably see in all of Ontario — and maybe even Canada — I’d say,” says Perrie, who has lived in the area for the past eight years. .  “You have five-star restaurants, you’ve got small diners, you also have a Christmas store that’s open all year round, it’s just incredibly romantic,” he says. There’s even a chocolate factory, he says, quipping, “Strawberries covered in chocolate, anyone?”

The market: “Niagara-on-the-Lake has a little bit of something for everyone,” says Perrie of the local real estate market. Around Queen Street, you’ll find custom and heritage homes. For a more suburban lifestyle, check the towns of Virgil or St. David’s, where there are more recently built subdivisions. “They offer an amazing family experience,” Perrie tells Wahi. 

5. Stratford: “The Festival City” 

The town: “It is the festival city,” Paul Schumm, a Realtor with Royal LePage Hiller Realty, tells Wahi, of Stratford. “It has the high culture of Shakespearean plays and arts and festivals,” he says. Notably, each year from April to October, the riverside town hosts the eponymous Stratford Festival, an acclaimed theatre festival, attracting lovers of the arts from all around the world.

There’s more to the town than theatre, though. “It’s just not all Shakespeare,” says Schumm, who mentions lots of other local entertainment, from comedy to dragon-boat races on the river. “We have a lot of great restaurants as well,” he adds.

In the winter, the town’s charming downtown glows with colourful lights, creating a perfect romantic backdrop for a weekend getaway. For some, the charms and romance of the town inspire them to relocate altogether. “People love to retire here, he says, adding that Stratford isn’t just a sleepy retirement community. “You have middle-aged people, and those just starting out,” he says. 

The market: If you’re considering a move, the town is friendly to first-time homebuyers. “It’s a very affordable market if you’re coming from one of the bigger centres,” says Schumm. “It’s got a small-town feel but has big-city amenities, is what I find,” he adds. “you’re going to be able to get from one side of the city to the other within 10-15 minutes on any given day.”