From the Gym to the County
The gainz she’d been envisioning turned out to be a gain of an entirely different kind. “Somewhere between the squats and the small talk, we both realized this was not going to be a long-term trainer-client relationship. Instead of counting reps, we decided to start counting dates. So technically, I set out to hire a personal trainer… and accidentally ended up with a boyfriend instead.”
Prince Edward County had always been their favorite place, and they often went there to reconnect and relax. And, after Jason surprised Allana with a trip there, it also became the place where they’d gotten engaged. So, when they began planning their wedding, the County was the only place in the world that felt right for their next step together.
When they found their venue, 100 Acre Wood, everything came together. “It reflects so much of what we love, especially the focus on food, warmth, and bringing people together. The owners, Mary and Kevin, used to own the Woodlot in Toronto, which is incredibly meaningful to us because it’s where Jason gave me my first promise ring. That connection made the choice feel really full circle.”
Next on the List: The Dress
When Allana began her quest for a timeless wedding dress, she had something specific in mind. “I always imagined myself in a lace, flowing gown, something romantic but still effortless.” At the same time, “Comfort was really important to me since I knew I’d be wearing it all day.” At our flagship Toronto bridal shop, she met her match in a bespoke gown. “Going the custom route felt like the perfect way to bring that vision to life while making sure it truly fit me in every sense.”
Our sweet bride shares more about their engagement and how they incorporated family tradition into their day below!
How did you and Jason meet?
Back in 2010, I was on a very noble quest to improve my fitness and find a personal trainer. My friend Richard casually mentioned that he knew a guy who had just moved from England and started personal training. Very professional. Very promising.
So, Richard introduced us, and we booked a session. One session. That’s all it took. Somewhere between the squats and the small talk, we both realized this was not going to be a long-term trainer-client relationship. Instead of counting reps, we decided to start counting dates.
So technically, I set out to hire a personal trainer… and accidentally ended up with a boyfriend instead.
How did you both know you'd met your match?
Jason: I knew she was the one when she went to Australia for two months and I realized life without her was simply not an option. Despite a brutal time difference that tried very hard to end us, we talked constantly and somehow made it through on sleep deprivation and love alone.
Allana: I knew the moment I met him. No jet lag, no long-distance test, no dramatic realization needed. I just knew.
How did you get engaged?
Jason surprised me with the most beautiful weekend getaway to The County. He planned everything, from a stunning stay at The Royal in Picton to days spent exploring wineries, wandering through charming little towns, and slowing down together by the pool. It felt special from the very beginning.
On Saturday, he suggested we go to Slake, so we grabbed a couple of beers and headed to Sandbanks for a hike. As we climbed the hill, I noticed he seemed a little nervous, but I brushed it off, never thinking that this was the moment.
As the sun set, he dropped to one knee and asked, “Allana Laura Cowley, will you marry me?” In that moment, everything felt perfectly still, and completely right.
We celebrated with the help of some kind strangers who captured the moment for us, and later that evening, Jason surprised me once again with a beautiful dinner at Bocado. Between the endless champagne and the overwhelming happiness, it was a weekend I will never forget.
Any special ways you incorporated your family or family history into your wedding day?
Tell us about your outfits! How did you choose your gown?
I always imagined myself in a lace, flowing gown, something romantic but still effortless. Comfort was really important to me since I knew I’d be wearing it all day, so going the custom route felt like the perfect way to bring that vision to life while making sure it truly fit me in every sense.
Jason’s tux was also custom from Garrison’s, which made it feel just as personal. He added a fun, unique touch with a custom design on the inside, a little detail that made it feel distinctly his while still looking classic on the outside.
Why did you decide to get married where you did?
Why we chose The County:
Prince Edward County has always felt special to us. It’s where we go to slow down, reconnect, and just be together. Every time we’re there, it feels easy and familiar, and it’s also where we dream about one day having a home of our own. Getting married there felt like choosing a place that represents both our relationship now and the life we’re building together.
Why we chose 100 Acre Wood:
100 Acre Wood felt right the moment we found it. It reflects so much of what we love, especially the focus on food, warmth, and bringing people together. The owners, Mary and Kevin, used to own the Woodlot in Toronto, which is incredibly meaningful to us because it’s where Jason gave me my first promise ring. That connection made the choice feel really full circle.
The space is intimate and welcoming, the staff genuinely care, and everything about it feels thoughtful and personal. It didn’t feel like just a wedding venue. It felt like a place that already held part of our story, which made it the perfect place to celebrate the next part of it.
What was the funniest moment of your day?
One detail you couldn't live without?
Allana: I couldn’t have done without the getting ready time at Cressy House. It was such a special, calm part of the day where I got to be surrounded by family and friends, soaking in the excitement before everything began.
Jason: The food from 100 Acre Wood, hands down. It was incredible and such a memorable part of the celebration.
What part of your wedding day was most important to you?
Jason: Watching my wife walk down the aisle to the sound of bagpipes was unforgettable. It was such a powerful, emotional moment and easily my favorite part of the day.
Allana: Our first look before the ceremony meant everything to me. Having that quiet, intimate time together before the celebration began allowed us to really be present and soak in the moment, just the two of us.
Allana + Jay’s Toronto Wedding Vendors
wedding dress: Lea-Ann Belter Cressida via the flagship Toronto bridal shop
| photographer: Tara McMullen Photography | getting ready venue: Cressy House | wedding venue: One Hundred Acre Wood | planning: Bliss Toronto | florals: Dahlia Thalia | invites + menus: By Modern Social | hair + make up: All Dolled Up Studio | film lab: C41 Film Labs
Were you a Lea-Ann Belter bride? We’d love to feature your day! Share your pictures and details with us.
