A decade after establishing the Drake Hotel and turning it into a bastion of cool, Jeff Stober, the city's hippest hotelier, is expanding his empire.
In some ways, the new Drake Hotel will be indistinguishable from his Queen Street boutique hotel/hotspot when it opens early next year – the art will be meticulously curated, the playlist handpicked by someone who knows better.
But anyone wanting to bask in the retro cool of the new property will need to do more than step off the 501 streetcar. They'll need to get in a car and drive 207 kilometres to Wellington, a picturesque village on the edge of Lake Ontario in Prince Edward County.
It's a long way from downtown Toronto, and represents an enormous challenge for Mr. Stober. Many deep pocketed investors have tried to bring cool to the county, only to find themselves thwarted by suspicious locals resistant to change and the fickle whimsies of the weekend jet set.
And if he does manage to win over the locals – a difficult task for anyone, let alone a dot-com millionaire who runs artsy hotels in the big city – his success could attract more ambitious, out-of-town interlopers anxious to develop another rural getaway of Torontonians desperate to spend the weekend anywhere other than the city.
For the village's 1,700 residents, most of them retirees who fled cities such as Ottawa, Kingston and Toronto for a quieter life, it's a pressing concern.
"We haven't done a good job of welcoming development over the last 20 years," says real-estate agent Jim Wait. "The community has always been a bit scared of what might happen. They are afraid this place could get turned into a Muskoka or Collingwood."
Mr. Stober brushes that all aside as he sits in the lobby of the Drake, somehow appearing both relaxed and tightly wound at the same time. His purchase of the former Devonshire Inn for $1.3-million should be seen as an isolated event in the village's history, he insists, not be watched as a barometer of the region's cool.
"We think the benefits to the county are multiple, never even mind all the eyeballs we'll bring by coming," he says. "We will authenticate our commitment to the local community, and locals who are interested in dining, in hearing music or seeing art will feel most welcome and appreciated."
An urban oasis in the country
The 52-year-old Mr. Stober, who started a headhunting firm in his early 20s and sold it at the height of the tech bubble, has been planning to expand the Drake brand from the minute he finished renovating the Queen Street location and flung open its doors in 2004. It's an eclectic mix of old and new, with locals drinking coffee at the bar in the morning and dancing maniacs from across the region spilling in at night.
Later this year he plans to knock down the eastern walls, allowing the property to spill into the adjoining lots he has been buying up for the last decade. He's also built two Drake General Stores, one on Bathurst and another on Yonge Street. The quirky shops offer a curated selection of curiosities, and a third location will be included in the Queen Street renovations.
His presence in the area was initially bemoaned by many who feared gentrification and worried about the hordes of partygoers the Drake was attracting to a region that was once better known for hookers than hipsters.
"It's funny when you look around here," he says, turning his head to look out at the lunchtime crowd walking past his Queen Street windows. "Everybody else is growing up, but we're the ones who are being true to our history and expanding outwards instead of upwards. That's so important to us, to maintain the history of the neighbourhood."
His experience along Queen Street has informed his approach to the county. He spends a lot of time talking about how the Drake Devonshire Inn, as it will eventually be called, will draw from the county's richest traditions when it opens and provide a cultural hotspot just as accessible to the locals as to vacationers looking for a good time.
"This isn't about building something for ourselves," he says. "This belongs to everyone."
As ambitious as his Toronto plans are, he's always wanted to build something in the country. He grew up visiting Quebec's Eastern Townships, a rolling countryside that draws tourists from the Montreal area year round and is markedly similar to Prince Edward County. Both regions, he points out, were settled by British subjects who opted to flee the United States rather than fight for its independence in 1775.
"I always thought it would be so positive to do something in the countryside," he says. "We had several ideas and looked at a lot of different things, but this site spoke to us and we decided it was the best fit."
Buying the former Devonshire Inn wasn't his first choice. He originally scoured the countryside – he pointedly avoids using the word "rural" because he worries the term comes loaded with judgment and presumptions – for a farm, with the intention of creating a weekend getaway that would see guests eat food that was grown onsite and pitch in with some of the day-to-day chores.
Inside, the six-room inn will trade doilies for coasters, and offer its guests locally sourced food and wine from down the road. There will be an old-school games room where visitors can play pool or backgammon as they listen to the waves lap up against the shore.
"We think of it as summer camp for grown-ups," he says, though it will operate year round.
Innkeeper-to-be Chris Loane is a veteran Drake employee, and also a veteran of Toronto's indie music scene, who will draw on his deep connections to attract musicians to play small, intimate sets.
"I left the corporate world appreciatively and happily," Mr. Stober says. "The point I would make is that we had offices in many cities and I was able to transport our DNA very effectively. That has everything to do with your people, and this is no different. They understand what we stand for, and will bring that with them to this new experience."
Converting the locals
There's no guarantee people will flock to his small, six-room hotel no matter how cool a property he develops. Other tastemakers have been drawn by the region's underdeveloped charm, only to find themselves surrounded by resentful townies and longing for the warm embrace of King Street West in the summer.
Mr. Wait, who grew up in the area, says the anti-outsider mentality has softened in recent years, as the locals come to realize the only way to maintain their quality of life is to build their municipal tax base. The region has seen trends come and go – barley farming during prohibition, tomatoes in the 1970s – and many residents have come to realize that despite the best efforts of wide-eyed developers, things never actually change that much.
"I've lived in the county all of my life and nothing changes really quickly," says the real-estate agent. "Folks that moved here in the last two years think that there are all kinds of big changes [coming] but it's always been more gradual than that. Things come, things go. You'll see a new restaurant come in and be at the top of its game and everyone says it's the greatest thing since sliced bread, and then the next one comes along and that's that."
The region's largest cities – Belleville and Trenton – are largely blue-collar centres struggling as manufacturers close and throw hundreds out of work. The region has suffered several recent setbacks, including cardboard maker Norampac's decision to close a local plant and Parks Canada cuts that could leave dozens more unemployed along the beautiful Trent-Severn Waterway.
Economic development officials have spent much of the last two decades rebranding the area with tourism in mind, mindful of the need to diversify. They've got a lot to work with – Lake Ontario is at its most dramatic near Sandbanks National Park, dozens of wineries dot the landscape and the region's farmers provide a smorgasbord of organic and meticulously cultivated crops.
While the region has attracted its share of high-end restaurants, not all have found success. One noted failure was Harvest, founded by Toronto chef Michael Potters and closed within five years of its much heralded opening. Mayor Peter Mertens says businesses come and businesses go, but it hasn't been a lack of clientele that has determined their fates.
"It generally hasn't been because of product offerings," he says when asked about Mr. Stober's prospects. "In a lot of cases it can be difficult on families, and that usually doesn't have anything to do with business plans. Whether you're a high-profile person or not, it takes a lot of work to make something like this a success and it doesn't happen overnight."
For Mr. Stober, success is something of an afterthought. He appears bored by questions about profits and brand, and waves off questions about the broader corporate world.
"Who will the customer be? We don't know," he says. "All we know is that we can prime the canvas, and then wait to see who makes it their own – that alone will be one of the best artistic moments."
Editor's Note: Belleville and Trenton Ont. are in Quinte region, not Prince Edward County. Incorrect information appeared in Saturday's paper and an earlier version of this article.