Footwear Wisdom from a Winery Season in The County

When you think about working as a tasting room hostess and tour guide at a winery, you probably imagine swirling glasses of Pinot Noir or strolling through sunlit vineyards with a pour of Chardonnay in hand (and it sadly does not include stomping grapes barefoot as my misleading title image suggests!). But my first season working in Prince Edward County taught me something far less glamorous and far more practical: if you don’t have the right shoes, even the best glass of Cab Franc won’t save you.

I went from sitting on my butt 100% of the day at my soul-sucking federal government job to suddenly working on my feet from morning till night at a spectacular winery in Prince Edward County. And let me tell you: my feet did not sign up for that plot twist.

That first week? Brutal. I was hosting tastings at the bar, carrying trays of wine glasses up and down a winding staircase to the basement dishwasher, leading walking tours across the estate, lugging cases of wine out to cars, and even shuttling giant tubs of gelato down to the freezer. At a dress size 22, my feet were already putting in extra work just to keep me moving. Add a full day of winery hustle, and they were staging a protest.

But necessity is the mother of invention (or in this case: survival). I had to figure out my footwear game, fast. And here’s what I learned.

1. The Midday Shoe Swap = Life Saver

No matter how supportive your shoes are, your feet get tired when you’re standing and moving all day. The single best trick I picked up? Change your shoes at lunch.

Even if both pairs are great, the shift in fit and support makes your feet feel brand new. My break routine was heaven: grab my lunch, slip off my shoes, and find a perch. Sometimes it was a retaining wall near a row of grape vines (with a cheeky little rabbit buddy who liked to hang out). Other times I’d sneak down to the dock, dip my feet in Lake Ontario, and let the cold water work its magic. After that reset—and fresh shoes—it was like starting a whole new day.

2. Running Shoes Are Not the Enemy

I used to resist running shoes because I had flashbacks of those 80s office ladies in shoulder pads and chunky white sneakers. Not a look I aspired to.

But at the winery, I gave in. And honestly? Game changer. I bought a pair of all-black Brooks runners, and they became my workhorses. Comfortable, supportive, and low-key stylish. And today, with the rise of the maxi dress + pristine white sneaker trend, running shoes are officially cool. Pair them with a flowing skirt and suddenly you’re not just practical—you’re fashionable.

3. Two Different Styles = Double the Support

It’s not just about having a backup pair of shoes—it’s about having two very different kinds of shoes. Think of it as cross-training for your feet.

At the winery, my everyday anchors were the sturdy black Brooks running shoes, while my backup was a pair of polished wide-width Clarks with a totally different fit. Swapping between the two gave my feet new angles of support, so they weren’t locked into the same pressure points all day. That variety was key to getting through long shifts.

If you’re traveling or working long days, pack two different styles. Your feet will thank you.

4. My Personal Shoe Hall of Fame

Since those winery days, I’ve tested a lot of footwear. Here are my current faves for exploring cities, wandering vineyards, or just making it through a long day on your feet:

And speaking of Merrell… I also have a pair of solid, comfortable Merrell winter boots. They’re already on my packing list for my Christmas trip to Quebec City — but that’s a story (and a blog post!) for another day.

The Last Step

That season in The County gave me more than just an appreciation for Pinot Noir and Cabernet Franc — it taught me that the right shoes can make or break an adventure. Whether you’re exploring vineyards, strolling city streets, or wandering new places, your feet deserve as much thought and care as what you pour in your glass. 

I’m working on my first Songwood Travel guide (starting with Ottawa!) and it will feature gentle walking itineraries where having the right shoe strategy makes all the difference. Follow me on Instagram or Facebook for updates, sneak peeks, and more comfort-conscious travel tips.