Bear Estate Engagement Photography | Melissa and Eddie

Cranberry Bear Estate engagement photos


I originally met these two rockers in the Dominican Republic wearing a bridesmaid dress and strumming a guitar – them, not me. See if you can spot them on this Punta Cana beach. Fast forward a few years and Melissa and Eddie are now engaged… and we’re getting our engagement photos on at Cranberry Resort’s Bear Estate in Collingwood.

So the good news is I managed to keep these two from popping twofies (two-person selfies are a thing – did ya know?) long enough to squeeze in our e-session.  The bad news, well there is no bad news – I absolutely love hanging out with Melissa and Eddie – two of the nicest, mostest fun people on the planet.  They’re getting married in beautiful Stratford next summer… needless to say I’m looking forward to the show these two entertainers put on. Until then, let’s hear their story below in their own words…

Connect with me… 
Facebook Vaughn Barry Photo Twitter Vaughn Barry Photo Instagram Vaughn Barry Photo

Cute Waterfront engagement photoWaterfront engagement photo


Melissa: Eddie and I attended the same high school in Hespeler, Ontario though with two grades between us, we didn’t cross paths at that time. We both have a strong love for music and throughout high school we were both involved in various music department classes and events. One such class included a guitar class, taken separately but taught by the same guitar teacher. Fast forward and five years later on May 22, 2010 I was reaching the end of a less than fantastic week. Enter: high school guitar teacher. At this time, this individual played live music and on this night, happened to be performing at a local Hespeler hangout called Ernie’s Roadhouse. I called up a girlfriend and her and I ventured out to Ernie’s to take in a night of music.

I vividly remember walking into a packed Ernie’s and scanning the layout for a place to sit. Enter: Edward Davis McKenna… and this is the moment I first locked with my future husband; a moment I refer to as the bridge between ‘life as I knew it’ and ‘my entire wonderful future’. Eddie strolled on over and asked if my friend and I would like a seat. I sat next to him and we introduced ourselves. Though he was there with a large group of friends, the two of us spent the rest of the evening talking, laughing, and getting to know one another.

Partway through the evening, our mutual guitar teacher called Eddie up on stage to perform vocals on the next song on the set list, a cover – Save Tonight by Eagle Eye Cherry. ‘Oh, he sings?’, I thought… *proceeds to floor me with talent*… ‘WOW. Yes, he sings’. I like to think he was singing only to me because that’s exactly how it felt. Blown away by the initial wonderment of the early evening and bonus talent of the late evening I spent the summer of 2010 promptly attending every gig with Eddie’s name on it… 7 years later, I think I’ve earned the title of #1 fan and am still attending his gigs with the same excitement I felt that night.

daisy flower

Eddie: Melissa and I met at a mutual music teacher’s show at a bar on Queen Street in our home town of Hespeler. Melissa and her friend were chairless and I found them seats and introduced myself. We continued the night together, talking and enjoying the music. A short time later, the musical entertainment invited me on stage to sing a song. From what I hear, this truly impressed the love of my life.


Melissa: I would say our first real date occurred one night after one of those 2010 summer gigs… Tim Hortons, 2AM. I remember tea (we loved tea… we still love tea). For me, that night holds the memory of our first kiss. We were fairly inseparable from this date forward.

Eddie: Tim Horton’s and green tea in the parking lot listening to Ray Lamontagne. We talked music, we talked life, and we shared our first kiss.

Guitar engagement photo


Melissa: At the risk of sounding like a cheese ball… always. I don’t recall a specific day or time, I just know I always knew I was going to be with this person. Ever since I’ve known him, I’ve referred to our relationship as the only thing in life that I know for sure.

Eddie: Early. It wasn’t long after we began dating that I shared how I truly felt about this girl. We were walking home one evening when I admitted that I never wanted to spend another moment away from her. We painted her bedroom wall with the words, ‘Your heart is my new home’; both a statement of my feelings and a song inspired by and written for her. Melissa inspires me every day and I continue to become the person that I want to be with her by my side.

Engagement ring photoBlack and white engagement photo


Melissa: Eddie’s family is of Scottish descent and much of his extended family lives in Scotland. Having visited a number of times in his life, it was always something he wanted us to experience together. June 23, 2016 we ventured out with his father and sister and boarded a plane flying over the pond to Bonnie Scotland. Unbeknownst to me, Eddie had purchased a ring nearly a month prior, asked my father, and informed every person in our immediate families and a good number of our friends. His sister, Jackie, held onto the ring and stored it through airport security.

I’m convinced the three of them (and everyone I know) may be professional actors because I never once sensed a thing, let alone sensed anything amiss amidst what I would later learn to be their apparent overwhelming anxieties through airport security (…what if Jackie’s purse is emptied and the ring is discovered? What if Melissa needs something in Jackie’s purse?… etc.).  Fortunately, all went according to plan. We landed in Glasgow on June 24th around 8AM Scotland time and from there, set off to a cousin’s home in Stirling – our destination for the next few days. Though we had been awake nearly 24 hours, due to the time change we knew we had to stay awake until evening to avoid any serious jet lag. While everyone else was running on adrenaline, unaware of the coming event, I was running solely on a welcoming Scots breakfast – sausage on a bun. After breakfast and just prior to departing the house for our first tourist destination – the Wallace Monument.

Fun pre-wedding engagemetn photo

Eddie asked me to change into a specific fancy outfit he knew I had packed. In my experience, on an airplane one wears airplane clothing – comfy, elastic airplane clothing. Still dressed in said airplane clothing, I looked at him like he’d gone mad because who in their right mind is wearing a fancy outfit to climb a tower of narrow winding stairs? Only later did I learn that he had an outfit picked out in which he planned to propose and thought it would be nice if we looked a bit fancy. However, once I shut down the stair hiking fancy outfit idea, he did some quick thinking and remained in his own airplane clothes so as not to appear suspicious.

We set off to the Wallace Monument and in true Melissa fashion, I began taking as many photos as a DSLR holds (1 trillion, I think). While I was busy photographing every rock and pebble (no phony distractions required here), Eddie and Jackie deviated away from the group to the top of the Monument while I meandered behind with Eddie’s dad and cousin. Once I reached the top, so focused on the photography of rocks, pebbles, and highlands and entirely unaware, I briefly acknowledged Eddie with an absent nod and looked straight past this very familiar man down on one knee beyond to the breath taking scenery. It was then that my brain caught up to my eyes and I became engulfed in shock and lost all reasonable speech. Atop a tower, the man of dreams and my reality asked me to marry him. Amidst the sounds of sobs and Scottish bagpipes, I replied, ‘YES!’… and in our ‘fancy’ airplane clothes, we were engaged.


Eddie: Some things just fall into place. In 2016, we were scheduled to head out on a family vacation to Scotland. When you have someone you want to give the world to, where do you go to express that? For me, my favourite place in the world – the Wallace Monument in Stirling, Scotland. A tower that overlooks Scotland’s beautiful valleys and highlands. I raced ahead to the top of the tower before she knew I’d left the group. As she attempted to capture the scenery during her climb, I, down on one knee patiently waited at the peak with my promise to her of love and lifetime devotion.

pre-wedding engagement photography at Cranberry Resort Bear EstaCranberry Resort Bear Estate photographyFireman pose engagement photo


Melissa: Eddie is an individual that everyone loves and looks forward to being around; within moments he can change the atmosphere from black and white to double rainbow status. His character is loud and his presence is known. In every definition of the word, Eddie is an entertainer. He is everyone’s friend and he is always in your corner. He is passionate about creativity, love, and family and I’ve never met another soul alike.

Eddie: Oh man! One thing!? What do I choose? Would it be her attention to detail, her love for our families and friends, her willingness for adventure? I would actually have to choose her big, beautiful smile. Every day of my life, I will hunt for that smile.

Sunset silhouette engagament Collingwood


Melissa: Is ‘everything’ an answer? I’m looking forward to the… everything. Aside from the everything, I’m most looking forward to Eddie’s reaction when we see each other for the first time that day.

Eddie: Her big, beautiful smile… finally being able to call her my wife and being able to celebrate what she means to me with as many of our friends and family as we can squeeze into our venue.

Sunset silhouette engagament photo



Bear Estate Engagement Photography in Collingwood, Ontario
Article Name
Bear Estate Engagement Photography in Collingwood, Ontario
A beautiful Cranberry Resort Bear Estate engagement photo session in Collingwood, Ontario.
Vaughn Barry
Vaughn Barry Photography
Vaughn Barry Photography
Pin It
Vaughn Barry

Vaughn Barry

Wedding Photographer at Vaughn Barry Photography
Outdoor Muskoka, Barrie, Collingwood and international destination wedding photographer based in Severn, Ontario (lower Muskoka). When I put my camera down you'll find me with my beautiful wife and 2 daughters or behind the bench as a local hockey coach.
Vaughn Barry
no comments
Add a comment...

Your email is never published or shared. Required fields are marked *