Wendy May is the owner of The Oakwood, a longstanding independent family restaurant located in Winnipeg’s South Osborne neighbourhood. Since taking over the business in March 2016, May has worked to transform the café into a welcoming, community-focused joint known for affordable, home-cooked comfort food, including all-day breakfasts, burgers, Chicken and waffles, meatloaf with mashed potatoes, and classic Eggs Benedict. Housed at 660 Osborne Street in a modest strip mall setting, The Oakwood prides itself on offering scratch-made dishes at prices that rival fast-food chains, while also providing custom catering and charcuterie boards.
What is your business called and what does it do?
We are called The Oakwood (or Oakwood Café if you go by the sign) and we are an independent small family restaurant that offers comfort foods with all day breakfasts, meatloaf and mashed potatoes, Chicken waffles, liver, Eggs Benedict, burgers and much more. We also offer custom catering and charcuterie boards. Fun fact, a family of four can have dinner at The Oakwood for about the same as hitting up the drive-through. We strive to be your favourite neighbourhood joint.
What made you want to do this work?
When I moved back to Winnipeg from the UK with my husband and kids, I wanted to try something different and not just simply keep doing the same jobs I had been even though I enjoyed it. The opportunity to purchase the Oakwood came up, and after a lot of discussion, I thought what’s the worst that can happen? We got on the ownership rollercoaster in March 2016.
What problem did you want to solve with the business?
Not anything specific, but under the previous ownership, many of the items were bought in rather than made, simple things like dressings and desserts that I knew could be done better from scratch. The menu when we took over was a huge eight pages and very confusing, trying to do a bit of everything and sometimes not very well, which was too much, so gradually we honed it to make it what it is today. Fun fact #2: if there is something on a previous menu you hanker for, if you ask and we can make it, we will.
Who are your clientele/demographics?
There is no one specific demographic, which is great, and it ranges from families with young kids to seniors and everything in between. We try to offer something for everyone at a reasonable price, which broadens the range of our guests. Sometimes we nail it, and sometimes we miss the mark, but we’re always learning. We are fortunate to have a solid regular clientele who have supported The Oakwood in its various forms for many years, and without them, it would feel like something was missing.
How does your business make money? How does it work?
That is a loaded question, and since COVID, we have not really recovered financially, and we have noticed this past year that with the economic instability and uncertainty, it has had an impact on our sales. The supply chain and overall cost increase on food, utilities, wages, etc., have added another layer of challenge to an always unstable industry. The bills keep coming, even if the sales don’t, so it works by being a constant juggling act of making the money you do have keep working in the most effective way.
Where in the city can we find your profession?
We can be found in the best neighbourhood, South Osborne, hidden in a strip mall that you can easily miss if you’re driving past. We always say, ‘Do you know where the Fort Rouge Leisure Centre and Park Theatre on Osborne is? We’re opposite the Safeway at 660 Osborne.
What is the best question a prospective customer could ask a member of your profession when comparing services? Give the answer as well.
“Why should we choose you?”
My reply would be, we offer fantastic home-cooked comfort food that makes you feel like you’re going to a friend’s house for dinner. You’ll feel like part of the family (the family you like spending time with). We may not be fancy or on the cutting edge of cuisine, but we are a small independent business that has been there for over 30 years, and some of our staff have been there almost that long. You’ll also be surprised to know that coming to us will likely cost less or the same as a drive-through and some of our chain competitors. We offer fabulous food at a fair price.
What is the best part about what you do? What is the worst part?
The best and worst part about what I do changes like the wind but I would say the best part is having such a great team who have been on this ride with me since 2016 and even though I get the eye rolls sometimes (ok more than sometimes), they are truly what keeps me going and not give up despite wanting to more than once. They do the heavy lifting in making The Oakwood run, and sometimes I think it runs better if I am not there (pretty sure our team would not argue about that most of the time). Our guests, of course, are what keep the doors open and keep our team employed. Literally, without them, we would not be here. We get that dining out is a luxury, no matter what your budget and in these times, that can rightfully take a back seat to groceries and bills so we are so grateful that we are able to tick along.
That brings me to the worst part, which is always worrying about sales, paying for everything and keeping the doors open. It is hard. Really hard, and that is not likely to change until people have more disposable income to play with. There is a lot of uncertainty going into 2026, and as we always have, we will keep going until we can’t.
What is your favourite joke about your own profession?
I saw this online the other day. Owning a restaurant is how you go from making $2000 a month to making $200. There are many others, but nothing that is appropriate for print.
Where can we follow you?
You can find us online with our website, on Instagram and Facebook. Keeping up on the socials is a full-time job these days.
PAY IT FORWARD: What is another local business that you love?
I can’t just name one, the neighbourhood is full of gems so if I may, in no particular order there is Vera for amazing pizza, Friend Bakery (who we get our buns from), The Park Theatre, Park Alleys, The Haberdashery (seriously cool hats), Monticchio for Italian, BMC Tacos (if you know you know), Chocolate Zen Bakery, Osborne Florists, Black Market Provisions, Hoagie Boys and so many more. The area just gets better and better with all the independent businesses for almost everything. Oh! I almost forgot Game Knight who not only the go-to place for all things game-related, they also supply us with some of the best local beer in their Dastardly Villain series. I mean it when I say, it really is the best neighbourhood in the city to be in!
