Hilltop Proposal Story | Boston Wedding Photographer

As a Boston area photographer, I have the honor of documenting many types of stories. Engagements, weddings, births, birthdays, family milestones….and proposals. Do you remember your proposal story? Seeing someone get engaged always triggers fond memories of my own. Seeing my little sister get engaged and being able to document the whole thing was the ultimate privilege.

The Set Up

When her fiance contacted me a few months ago to discuss rings, I was sworn to secrecy. He knew she would want to be around her family when it happened (I mean, who wouldn’t want to be around us?!). A Spring break visit to her nephews was the perfect cover story. The original plan was to spend the day in Boston seeing the sights and end with a proposal in the Boston Public Garden. Mother Nature had other plans. With a washout predicted, Marcus and I had to come up with a second plan.

My oldest attends preschool at a farm school with a beautiful trail on the property. Plan #2 was to pick him up from preschool, hike to the top of the hilltop where my parents would be hiding, and surprise her with the proposal. All week I nervously checked the forecast. In typical New England fashion, rain was predicted initially. Luckily, it changed the evening before to partly cloudy. That morning, the plan went into motion. I nervously stashed a bottle of champagne, two glasses, and the diamond ring in my diaper bag. Her fiance and I convinced her to dress up a bit so we could do a couples photo shoot for my website while we were out. I suggested she wear my red boots…a pop of red would be perfect with a dreary March backdrop!


The Proposal

Confident that I had avoided the ugly-outfit-for-proposal snafu, we embarked on our adventure. In classic two-year-old fashion, my middle child was having a meltdown after pick-up. Auntie Taylor suggested we skip our hike and go home. Marcus and I exchanged nervous glances and hurriedly said “he’ll be fine, we are already here, let’s just do it!”. As we began the trek up the hill, I could see my father’s shiny bald head (sorry Dad!) peeking over the top of a huge boulder and then disappearing. My oldest sprinted ahead to the rock and disappeared behind it. My parents later told me that he nearly fell over in shock when he saw his grandparents hiding behind it.

When we reached the summit, they emerged surprising Taylor who thought they had just come for a surprise visit. Marcus called her over and then suddenly she realized what was happening. I’ll let the photos do the rest of the talking for me but we could not be more thrilled for these two and love Marcus like part of our family already!

PS- I learned I can take decent photographs while also crying. Did I mention that we are Italian? There were lots of tears all around.


My sister told me later that she was so happy that she has these photos to look at because in the moment it’s hard to focus on everything that is going on. I couldn’t have been more thrilled to be able to show her what happened and help her forever remember with these images.

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Are you or someone you know proposing in 2019?

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