Proposal in Erin by Hillsburgh Pond

Erika and Andrew’s surprise proposal in Erin was one of those special sessions that required careful planning, family involvement, and a believable story to keep the surprise intact. What Erika thought would be another couples’ photo session quickly became one of the most emotional moments of their relationship, photographed around Hillsburgh Pond and the beautiful Elora Cataract Trailway.

The proposal was the result of a long connection between me and their family, making this session even more meaningful to me. With Andrew’s family helping behind the scenes, we were able to create a completely natural experience that allowed Erika to enjoy the moment without knowing what was about to happen.

Surprise Proposal in Erin at Hillsburgh Pond

Erika and Andrew’s Proposal in Erin was a carefully planned surprise proposal photographed by DA Photography near Hillsburgh Pond and the Elora Cataract Trailway. Andrew contacted me in advance to organize the surprise, with help from his brother and sister-in-law, who helped create a believable reason for the couple to meet for a photo session. Erika believed she was simply having another couples’ photography session, similar to one we had done previously.

The proposal took place during golden hour near Hillsburgh Pond, behind the Hillsburgh Library in Erin. With their two dogs included in the session, I photographed the couple naturally before positioning Erika so Andrew could surprise her with the engagement ring. Once Andrew got down on one knee, I stepped back and documented the emotional reaction as the surprise unfolded naturally.

After the proposal, we continued the engagement photo session along the Elora Cataract Trailway, using a wooden bridge, open fields, tall grass, and warm backlighting to create more relaxed and romantic images. The combination of the natural surroundings, their dogs, and the newly engaged couple created a gallery that reflected both the surprise and the excitement of the moment.

This Proposal in Erin became part of a longer relationship with Andrew and Erika’s family. After photographing their surprise proposal, I later photographed their 1 Hotel Toronto wedding, continuing a family connection that began more than a decade earlier.

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The Family Story Behind This Proposal in Erin

To connect this proposal to how I met my couple, I had to go back more than 10 years to describe the amazing bond I share with their family.

I met Adam, Andrew’s brother, and his wife, Christina, many years ago when I photographed their young family at Loafer’s Lake in Brampton.

We had an amazing time, and since then, I have had the pleasure of capturing the arrival of their second son and their new addition to the family, their lovely daughter.

As I moved to Guelph and they relocated to Erin, I was able to keep in touch with them. A couple of years ago, after our fall session with the family, Adam shared my contact details with his brother Andrew when he met Erika to do their winter couples’ photo session. They had met a couple of months earlier, and that session was a genuine couples’ shoot. Andrew had presented it as a Christmas gift to Erika.

During that session, I met Andrew and Erika for the first time, and we connected perfectly. The next time Andrew contacted me was at the beginning of planning this surprise proposal in Erin, just behind his brother’s house.

To make things less obvious, Andrew and Christina had scheduled their family photo session right before Andrew and Erika arrived, so I was able to connect with them again and capture some new and updated family photos.

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Close up photo of a puppy during an engagement session

Photo of a puppy during an engagement photo session

The Couples Session Before The Surprise

When Andrew and Erika arrived, they brought with them the two lovely dogs that I had met a couple of years earlier.

As we planned with Andrew, he wanted to pop the question midway through their photo session, so we captured some pre- and post-proposal images.

The location where we did their photos was right behind Hillsburgh Library, next to Hillsburgh Pond in Erin. We had beautiful views of this part of the Elora Cataract Trailway, which made the photo session very colourful and vibrant.

As we started the session, I listened to what Erika wanted, knowing that their style is more candid and less posed. Having worked with me before, the two of them were relaxed, and we took photos by the pond, including their dogs in most of the images.

Erika couldn’t predict what would happen, and Andrew was a bit nervous as the big moment approached.

It was later in the afternoon, right before golden hour, and the sun was coming through the branches and the remaining leaves on the trees. It was a great location for their proposal in Erin, and I was excited yet nervous because I did not want to miss the amazing lighting I was experiencing.

Proposals by Hillsburgh Pond in Erin

Erin Proposal by Hillsburgh Pond

Proposal at Elora Cataract Trailway

 Proposal by Hillsburgh Pond in Erin

Erin Proposals

The Proposal in Erin by the Hillsburgh Pond

At one point, Andrew had to use the nearby washroom at Hillsburgh Library while I continued working with Erika and their two dogs.

They were so connected to Erika that I was able to recreate some of the photos that we took a couple of years ago when they were little puppies.

Andrew, in the meantime, had gotten the ring box and was coming back to the location where we were waiting for him.

This was the sign that their surprise proposal in Erin would happen in a couple of minutes.

As I positioned them so Erika could be turned with her back to Andrew, he went down on one knee, and I asked Erika to turn so I could take the photo. I did all of that so I could buy Andrew some time to open the ring box and get down on one knee.

I knew that once she saw the ring, most of the photos would be candid and documentary, so I stepped back and let the moment unfold naturally.

Writing this post, I still have chills and happy tears from the emotions I captured at that time.

Erika was so surprised that only the tears in her eyes could tell the right story. At the same time, the dogs were a bit confused, not knowing why their human mommy was crying while Andrew was down on one knee.

With so much excitement and fast-paced moments, my stepping aside gave my couple time to enjoy and reflect on the moment without me with the cameras up in their faces. From a safe distance, I captured this amazing moment in their lives and preserved it in great photos.

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Photo of an engagement ring have been sown to the dogs

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Engagement Photos Along the Elora Cataract Trailway

As Erika received the ring, she was happy to show it to their fur babies, while Andrew breathed heavily as the weight of this moment lifted from his shoulders.

“You did amazing,” I said to him in a quiet but reassuring voice.

As the surprise element of this proposal in Erin was behind us, I wanted to create some more romantic and intimate images that would be even more meaningful after the engagement ring.

We moved to the other side of Hillsburgh Pond, away from the pond and towards the Elora Cataract Trailway.

Here, I noticed a wooden bridge next to an open field, and I was already planning how it would work for my couple.

As I sat them down on the bridge, I was able to create some amazing images of them, now in a more relaxed atmosphere.

As we stood up, Erika saw the fields with the amazing tall grass, perfectly backlit, and asked me if we could go there. “For sure,” I replied, as I had already had that in mind, but now, coming from my couple, it was way more meaningful to them.

As I posed them in the field, I enjoyed the vibrant look of this serene location, and now, coincidentally, the two of them in it created picture-perfect scenery.

In the fall, the sun sets much earlier than in summer, so I did not want to run out of sunlight, because that would mean it would be cold for all of them as well.

As we were coming back to the cars, I took many pictures of them and their dogs, so we had completed everything that we wanted.

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From Proposal in Erin to Their Toronto Wedding

Andrew couldn’t wait to share the news with his brother’s family, who were patiently waiting at home for the couple to arrive. They had been so supportive and helpful with this, so Andrew and Erika couldn’t wait to share the news with the rest of the world about this surprise marriage proposal in Erin.

I was happy that we were able to plan, organize, and complete this proposal in Erin. My client wanted it, and I went home eager to finish those photos in no time so I could share them with my couple, who would then share them with their friends and family.

The following year, Erika and Andrew booked me for their Intimate Wedding at 1 Hotel Toronto in Spring, and I was thrilled to document their amazing city-vibe wedding.

Meeting their family again was very special for me because I was their family and wedding photographer, which they all enjoyed and respected.

Having a chance to work with the same family over and over is a true blessing. I connect with everyone and, over the years, capture their family’s growth and present it to them in the way they have shown me. I always feel the vibe of each session and showcase it as it is, keeping my clients’ likes and needs in mind.

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My Approach to Surprise Proposal Photography

Photographing a surprise proposal is very different from photographing a regular engagement session. My job is not only to create beautiful images, but also to protect the surprise, understand the location and lighting, anticipate the moment, and give the couple enough space to experience it naturally.

I don’t want a proposal to feel like a staged photo session. Once the question is asked and the surprise happens, I step back and allow the couple to experience the moment together while I document their genuine reactions.

The best proposal photographs are often not the perfectly posed images. They are the photographs that bring a couple back to exactly how they felt when the question was asked—the surprise, the tears, the laughter, the excitement, and the first moments of realizing that their lives are about to change.

After the proposal, I also like to continue the session while those emotions are still fresh. This gives the newly engaged couple an opportunity to relax, enjoy their engagement, and create beautiful portraits without making the entire experience feel overly staged.

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Proposal in Erin — Session Details

  • Location: Hillsburgh Pond, Erin, Ontario
  • Nearby location: Hillsburgh Library and the Elora Cataract Trailway
  • Photography: Surprise proposal and engagement session
  • Season: Fall
  • Time: Late afternoon and golden hour
  • Pets: Two dogs included in the session
  • Photography style: Candid, documentary, natural and romantic
Frequently Asked Questions About Proposals in Erin
  • What are some good locations for a surprise proposal in Erin?

Erin and the surrounding area offer many beautiful natural locations for a surprise proposal, including parks, trails, ponds, open fields, and quieter outdoor spaces. Hillsburgh Pond near the Elora Cataract Trailway worked particularly well for Andrew and Erika because it provided a natural setting for a couples’ photo session while also giving us beautiful scenery for the proposal and engagement photos afterward.

  • Is Hillsburgh Pond a good location for a proposal in Erin?

Hillsburgh Pond can be a beautiful choice for a proposal because of its natural surroundings, walking trails, water views, and nearby open fields. For a surprise proposal, I also look for locations where the couple can move naturally without making the proposal feel staged. In Andrew and Erika’s case, the area allowed us to photograph their couples’ session first and then transition naturally into the surprise proposal.

  • What is the best time of day for proposal photos in Erin?

Late afternoon and golden hour can be excellent for proposal photography because the softer light creates more flattering and romantic images. The exact timing depends on the season, location, and the type of photographs the couple wants. I usually plan enough time before the proposal for natural couples’ photos and then continue photographing after the proposal while the emotions are still fresh.

  • How can you plan a surprise proposal without your partner finding out?

The most important part is creating a believable reason for being at the location. A couples’ photo session, family gathering, walk, picnic, or another activity can work well. I also recommend planning the exact proposal location and timing in advance, communicating privately with the photographer, and keeping the plan simple enough that it does not attract attention. For Andrew and Erika, the couples’ photo session was a natural explanation because we had already photographed together before.

  • Can we include our dogs in a proposal or engagement photo session?

Absolutely. Dogs can be a wonderful part of a proposal or engagement session, especially when they are an important part of the couple’s life. I usually recommend photographing some images with the dogs before the proposal so they can be included naturally without becoming a distraction during the actual moment. After the proposal, we can continue with both dog-friendly and couple-only photographs.

  • Can engagement photos be taken immediately after a surprise proposal?

Yes, and I often recommend it. Once the proposal has happened, the couple is usually experiencing genuine excitement and emotion, which can create beautiful natural engagement photographs. We can begin with candid reactions and gradually move into more intentional portraits as the couple relaxes. This also means the proposal and engagement photos can become part of one complete story.

What Makes a Great Surprise Proposal Photo?

A great proposal photograph isn’t simply the moment someone gets down on one knee. It is the complete story—the anticipation, the surprise, the reaction, the engagement ring, the hugs, the tears, and everything that happens immediately afterward. I deliberately step back after the proposal so the couple can experience the moment without feeling like they’re performing for the camera.

Thank you, Erika and Andrew, for choosing me to capture your life milestones. I’m thankful and honoured to be part of your story. I will be waiting for our next session whenever you are ready.

Photos taken by Dragi Andovski, published ©2026 DA Photography
Engagement photography location: Hillsburgh Pond and Elora Cataract Trailway, Erin, ON.

Check this surprise proposal blog post and another amazing engagement session after proposal in fall. View our post ” Elora Mill Proposal: How It All Came Together Perfectly” for some inspiration if your planing an proposal or engagement photo session.

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