Restaurateur? Who, me?

Five years and one pandemic in, Oakwood Café owner decides the job she didn't think she was qualified for is the one she should have had all along


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Yolk-stained hands up if you’re familiar with a whimsical set of Egg Farmers of Canada commercials in which actors portraying characters who are rather odd in their own right opine eating eggs for dinner is “weird.”

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Hey there, time traveller!
This article was published 24/10/2021 (465 days ago), so information in it may no longer be current.

Yolk-stained hands up if you’re familiar with a whimsical set of Egg Farmers of Canada commercials in which actors portraying characters who are rather odd in their own right opine eating eggs for dinner is “weird.”

Wendy May was met with a similar reaction in the spring of 2016 when she proposed introducing an all-day-breakfast option at the Oakwood Café, 660 Osborne St., weeks after she purchased the 56-seat nook. Some of the existing staff informed her that wasn’t possible, as the temperature the flat-top grill is set at differs if they’re preparing an omelette versus lunch and dinner selections.

Surely they could find a way around that dilemma, she offered, explaining it was her experience every grill had what she termed a “sweet spot,” not too hot, not too cool.

Wendy May in her kitchen. May moved to England several years ago, but strangely enough, began missing Winnipeg’s winters. (Mike Deal / Winnipeg Free Press)

“I grew up eating pancakes or toast and eggs for supper and to me, that was the greatest thing in the world,” May says, adding all-day-breakfast, be it huevos rancheros, French toast or (yes, please) chicken chorizo waffles, proved an immediate hit at the Oakwood, which opened as Samantha’s in the late 1980s only to be renamed for a neighboring street a few years later.

Of course, it goes both ways. Shift workers who get off at 8 a.m. think nothing of diving into a clubhouse and fries, or a heaping bowl of borscht, first thing in the morning, she points out.

“One of my goals when I took over was to streamline (the menu) a bit, by concentrating on what we do well, which is homestyle breakfast, burgers and sandwiches. Our regulars seem to appreciate the fact they can pop in for their favourite dish, no matter what time of day it is.”

If this had been any other year, May would have had a laundry list of reasons to celebrate. In addition to 2021 marking five years since she bought the Oakwood, the married mother of two daughters, ages 18 and 11, turned the big five-O in July and toasted her 25th wedding anniversary the following month. Alas, after everything she had been through owing to COVID-19, she wasn’t feeling overly jubilant, she admits.

“Never mind the end of my rope, I was… dangling by a single string around this time last year,” she says, seated near a newly painted feature wall boasting oversized, teal-and-white images of some of the resto’s most popular selections. “It’s really too bad because before all of this happened, I was just starting to relax as owner a little bit more, feeling I didn’t have to be here every second of the day; that we have an excellent staff that was more than capable of handling things on their own. Then, all of a sudden, the world went topsy-turvy and in a lot of ways, it was back to Square 1.”

Patrons relax and enjoy the food and casual atmosphere. Some customers are like clockwork: they arrive at the exact same time every day, sit at the same chair at the same table and order the same meal. (Mike Deal / Winnipeg Free Press)

May never imagined herself a restaurateur when she was growing up in East Kildonan. Her family rarely ate out and when they did, it was somewhere “posh” like Alycia’s or Kelekis, she says with a chuckle.

She attended high school at Tec-Voc, where she studied to be a dental assistant. It was a job she neither loved nor hated, she says, but at age 24, she decided a change was in order. Following a weekend soirée where she got, as she candidly puts it, “completely hammered,” she boarded a flight to England, having determined that was where she wanted to live after spending three weeks there the previous summer.

She successfully applied for a two-year work visa and about a year into her stay, while toiling as a receptionist at a London hair salon, she met her future husband, Rick, who had popped in for a trim. Picking up on her accent, or lack thereof, during their first date, he inquired what part of the United States she was from. “The Canadian part,” she deadpanned.

The couple visited her family in Winnipeg regularly, before and after their daughters were born. Although May had sworn to never dwell here again — “You could have strapped me to a lie detector machine under a hot lamp and my answer still would have been no” — she began to waver somewhat in 2012, following a stay at her brother and sister-in-law’s place in St. Vital.

“Their daughter is about 10 months older than our youngest, who was only two at the time, and I started thinking how nice it would be for them to grow up together,” she says. “Plus, even though it sounds funny to say, I kind of missed winter after however many years of watching it rain, October through March.”

The Oakwood Cafe, a South Osborne mainstay famous for its borscht. (Mike Deal / Winnipeg Free Press)

The first thing the Mays did after moving to Winnipeg was go house-hunting. When it was time to secure a mortgage they were recommended to Peter Paley, who in addition to running his own brokerage firm, was also the owner of the Oakwood Café, located directly next door in the same, South Osborne strip mall. May and Paley hit it off immediately, to the point he encouraged her to study for her broker’s license, too.

She did just that, and before she knew it, she wasn’t only working for Paley, she was asking, “Uh, what smells so good?” when scents from the Oakwood’s kitchen drifted past their desks.

From time to time Paley mentioned his goal was to eventually sell the restaurant to concentrate solely on his mortgage biz. May shrugged him off every time he said she should buy it from him, commenting, what did she know about running a restaurant? As much as he did when he succeeded his aunt there in 2006, he’d reply.

Curious, May began pulling the occasional restaurant shift. She also enrolled in a 12-month baking class being taught at Red River College, expressly to determine if that might be something she’d enjoy doing professionally. Satisfied it was, she finally took Paley up on his offer in March 2016, when she became the Oakwood’s new proprietor.

Like she said, everything was going along swimmingly before COVID struck in the spring of 2020. May and her family were vacationing in Hawaii when word of the pandemic began to spread but she assured her husband, no worries, it wasn’t going to become “a thing” in Canada. Weeks later, closed for in-person dining, she was forced to think on her feet, and fast.

John Lindenbach, kitchen manager at The Oakwood Cafe, cracks some eggs. (Mike Deal / Winnipeg Free Press)

“Pick-up and delivery had never really been a consideration here before, we weren’t signed up with any of the services… we didn’t even have proper take-out packaging,” she says. “But we were getting so many emails and messages from regular customers telling us they wanted to support us any way they could that we were like, ‘OK, we have to figure this out.’”

May credits one of her servers for a “genius” move; that was, to include a postcard in each and every takeout order asking the recipient to personally contact the restaurant directly if there was anything even remotely wrong with their meal, versus posting an anonymous review online. “We wanted to make sure they knew this was all new to us, too, and to let us know what we could improve on the next time,” she adds.

Now that capacity is back at 100 per cent, long-time patrons are trickling back in, slowly but surely. That includes a single gent in his 80s named Bob, who, pre-COVID, ate the same thing at the same table every morning, to the point if he was 15 minutes late staff were on the horn, calling to check whether he was OK or not.

May, who spends the majority of her time in the kitchen cooking and baking, mentions the menu is slowly getting back up to speed, as well, pointing out a number of popular items were temporarily dropped during the slowdown. Among those is a nod to her days across the pond: a traditional, full English breakfast, consisting of three eggs, bacon, sausages, sauteed mushrooms, grilled tomato slices, baked beans and fried bread.

“We haven’t put that one back on yet but if people ask for fried bread, we’re still happy to make it for them,” she says, describing the calorie-rich dish as slices of rye or whole wheat fried in bacon fat.

A pot of cooked beets which will be made into the cafe’s famous borscht. (Mike Deal / Winnipeg Free Press)

Checking her phone, May announces oops, she has to run as she’s due to pick up her youngest from school in five minutes. Before heading out the door, though, she promises to get around to that birthday or anniversary cake in the not-too-distant future.

“When I first bought the place I wasn’t entirely sure it was the right move, and during COVID I was almost convinced that was the case. But now that there’s light at the end of the tunnel, I can safely say I’m glad I took the risk in the first place, and that after however many jobs I’ve had in the past, this might just be the one I was meant to do, in the first place.”

David Sanderson writes about Winnipeg-centric restaurants and businesses.

Lindenbach puts together a chicken salad sandwich. (Mike Deal / Winnipeg Free Press)
Lindenbach adds fries to a chicken salad sandwich plate for a customer. (Mike Deal / Winnipeg Free Press)
The proprietor puts out some locally produced honey that she sells along with other local products. (Mike Deal / Winnipeg Free Press)
May concocts some pickled onions. (Mike Deal / Winnipeg Free Press)
May works on a possible new addition to the menu, maple bacon cinnamon buns. (Mike Deal / Winnipeg Free Press)
May’s pickled onions are a treasured treat. (Mike Deal / Winnipeg Free Press)
May, who spends a lot of her time baking, works on a possible new addition to the menu, maple bacon cinnamon buns. (Mike Deal / Winnipeg Free Press)
The Oakwood Cafe, 660 Osborne St., a South Osborne mainstay that celebrated its 30th anniversary last year, albeit not in a very celebratory fashion. Wendy May purchased the restaurant five years ago but hasn’t paused to bake herself a fifth anniversary cake, things have been such a struggle the last 20 months. (Mike Deal / Winnipeg Free Press)

David Sanderson

Dave Sanderson was born in Regina but please, don’t hold that against him.

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