Cathy and Kevin’s waterfront engagement photo session in Oakville took place across four meaningful locations, each reflecting their personality and connection. We began at Westwood Park for candid, natural photos in soft afternoon light. From there, we moved to Tannery Park on the quieter side of Oakville Harbour, where the marina backdrop inspired some of their most intimate images. At Gairloch Gardens, we embraced the vibrant rose garden and glowing sunset before finishing at John Cabot Catholic Secondary School in Mississauga—the place where their story first began. The session blended natural, unposed moments with beautiful waterfront scenery, creating a diverse and heartfelt collection of engagement photos.

I first met Cathy at her sister’s wedding a couple of years ago. During Dorota and Glenn’s wedding, Cathy was the maid of honour, and that’s when we were introduced. I met Kevin later that night—he was absolutely rocking the dance floor.

When Cathy reached out to book me for their Ancaster wedding, I was so excited because they were such a down-to-earth couple and truly wonderful people to work with. While planning their engagement photos, Cathy mentioned that they really wanted some waterfront photos. It didn’t surprise me at all, since Dorota and Glenn’s engagement photos were taken in a similar setting—just on the opposite side of Lake Ontario at the Scarborough Bluffs.

The First Location of Their Waterfront Engagement Photos

For their first location, Cathy asked me to meet them at Westwood Park, a cute little park in Oakville. Since we had planned their engagement photos for mid-afternoon, it turned out to be the perfect time to start the session there.

From our earlier conversations, I picked up that neither of them was much of a “poser,” so I knew natural, candid, unposed images were the direction to take. To achieve that style, I needed to connect with both of them so the nervousness could lift and I could capture those spontaneous moments.

The park was empty, which I loved—especially knowing they were feeling a bit nervous. In a small park like Westwood Park, I always try to pair each scene with the lighting that complements it best. On this summer day, the sunshine was bright but not overpowering.

I decided to work here using only available light, saving the off-camera flash for later in the day. The vibrant colours of the gardens were fantastic, and starting the session in this spot turned out to be the perfect choice.

As I used every corner of the park to give them a unique perspective on their chemistry, I could see their initial uncertainty and fear of being photographed slowly fade away. That was the perfect moment for us to move on to the second location for their waterfront engagement photos.

Tannery Park Photos in Oakville, Lakeshore Area

Although I had never photographed on that side of the Oakville harbour before, I often work on the opposite side, near the lighthouse and my favourite spot, Erchless Estate.
Once we arrived, I immediately saw this part of the Waterfront area in a completely different light.

This side of the harbour was quieter, with less foot traffic, making it perfect for more intimate photos.
Seeing what Cathy and Kevin envisioned here, I focused on completely candid coverage—letting them walk naturally and, from time to time, guiding them into spots that showcased the beauty of their waterfront engagement photos.

Eventually, we reached a shaded area directly across from the harbour, using the marina and the boats behind Cathy and Kevin as our backdrop.
It was here that I captured one of their most intimate photos. They were so relaxed at this point that the images looked completely different from anything we had taken earlier at the park.

Feeling happy with how many unique photos we created in this spot, we decided to head to two more locations.
The first was one of my absolute favourite places in Oakville—Gairloch Gardens.

Waterfront Engagement Photos at Gairloch Gardens

We arrived at Gairloch Gardens, and knowing I can easily get lost in this place, we set a timer to work on the sunset photos while still leaving enough time to travel to the last location, which was very special to them. That location was John Cabot Catholic Secondary School in Mississauga, where they both met.

Now already in tune with our favourite poses and the way we interacted with each other, I started working in the rose garden to give them a look that wasn’t present in the previous waterfront engagement photos.

I was excited to move from scene to scene quickly because we had already established a rapport that worked well for all of us.

I took Cathy and Kevin to my signature spot within Gairloch Gardens. Once we finished the very last photos there, the sun set, giving us just enough time to arrive at the final location for their waterfront engagement photos.

As the full moon rose on the horizon, it extended the twilight, and I was rushing to reach the school and capture some of it in our photos.

Arriving at the school for the final set of these waterfront engagement photos felt like just another stop for the day, but this location was deeply meaningful to my couple. It held unforgettable memories from their time here, along with the feeling of being fully present in a place that mattered to them.

The High School Love Revisited

Both of them were so happy, and I found myself unsure of what to photograph first. Twilight had turned the sky a deep blue, and I needed to work quickly to decide on my angles and set up my off-camera lights.

I knew I wanted to capture the school name in the photos. For the second set, I focused on the school entrance and the silhouettes of my couple. The final images I aimed for were of them walking away from the school grounds, using a high ISO and adding a touch of motion blur to their steps.

I converted these into black and white as the last images of the session, knowing I wanted to end their Waterfront Engagement photos with that symbolic walk. I became so absorbed in capturing the final shots that when we finished, I suddenly realized I had been working in a very dark area, illuminated only by the full moon overhead.

Cathy and Kevin felt thrilled that we could include four unique locations for their waterfront engagement photos, which gave them a fantastic variety of images.

I can’t wait to photograph their wedding once they set their date.

Check Erika and Stan’s engagement at Gairloch Gardens. View our post “Oakville Engagement with a Romantic, Artistic Glow” for some inspiration for your engagement photos with multiple locations.