Why We Keep Coming Back to the Winona Peach Festival - And Why It Means Everything to Us

If you live in our lush part of Ontario, you know that every August, something happens that reminds us exactly why we do what we do. The Winona Peach Festival comes around, we set up our booth in the Commercial Exhibit area, and within minutes the community finds us!

This year the festival runs August 28, 29 and 30, 2026 at Winona Park on Barton Street - just a short drive from our home in Grimsby, and we are already counting the days. The Winona Peach Festival is one of Ontario's top 100 festivals, completely free to attend, and entirely run by volunteers and not-for-profit organisations. Parking may come at a small cost, but there are shuttles in addition to parking at Puddicombe farms and various stops nearby. That spirit of community giving? It's exactly our kind of place.

IT'S ABOUT SO MUCH MORE THAN PEACHES

Yes, the peach sundaes are legendary. Yes, the peach pies and cobblers and ice cream are worth every single calorie. But what keeps us coming back year after year isn't just the food it's the people. Our kind of people.

Over the years, the Winona Peach Festival has become one of our favourite ways to meet families from all across Ontario. Families from Hamilton, Toronto, Burlington, Fonthill, and everywhere in between all gathered together in one beautiful, unhurried place. And yes, those peach sundae lines are absolutely worth the wait. We've had some of our best conversations with future clients while standing in line together, peach in hand, nobody in a rush. Just like a vacation, people come to slow down. To be with each other. We don’t know how long these kinds of festivals will last, but we hope it’s forever.

EVEN THE VENDORS BECOME FAMILY

One of our favourite things about returning to the Commercial Exhibit area each year is the vendors we've come to know and love. What started as neighbouring booths has grown into genuine friendships. These are the kind where you pick up right where you left off, year after year. There's something beautiful about that. Just like our Italian routes, the idea that the people around your table, or in this case your booth, become your extended family. That's what the Peach Festival has given us. Thank you SO much if you are one of our tried and true booth buddies!

COMMUNITY, CHARITY, AND PEACH PIE

What makes this festival truly special is its heart. The charitable peach pies and ice cream showcases are delicious (and iconic), but they also represent something we deeply believe in: that food, community, and generosity belong together. The festival is run entirely by many local not-for-profit organisations and every volunteer shows up because they love what this weekend represents. We feel right at home. Some of them have become dear clients to us too. We absolutely adore you guys!

COME FIND US FOR A GIVEAWAY TOO!

So, if you're heading to the Winona Peach Festival this August, come say hello at our booth in the Commercial Exhibit area. Every year we run a giveaway that includes a night's stay in Niagara Falls Canada, a carry-on bag, and other travel goodies. Just visit our tent and fill out a 2 line ballot in person. We'd love to meet you, talk travel, and maybe share a peach sundae. No pressure, no sales pitch, that’s not how we role, or what the festival is about. We will always love a conversation about where your family might go next though.

THIS IS WHY WE TRAVEL AND WHY WE HELP YOU DO THE SAME

At the end of every Peach Festival weekend, we drive home full of peach pie, a little sunburned, and genuinely happy, because we spent three days surrounded by community. By connection. By families enjoying each other.

That feeling of being together, and of the world feeling a little warmer and slower is exactly what we try to create for every family we send on a trip. Community at its core. We hope to see you at the festival folks! Is this up your alley, or do you prefer checking out local businesses in different ways?

Travel With The Finocchis · Grimsby, Ontario · finocchi@playcationtravel.com