Hilary and Lindsay

Proposal Ideas Chilmark, Massachusetts (Martha's Vineyard)

How We Met

Lindsay and I were introduced by a mutual friend who knew that we both shared a love of food/cooking and that we had both grown up spending a significant amount of time on Martha’s Vineyard. On our first date, we realized that Lindsay’s grandparents and my parents were neighbors and had actually known each other for years! Not only did we have our love for this beautiful island in common, but we also built sandcastles on the same beach as toddlers, learned to drive on the same road as teenagers and watched the same sunset as young adults. We had grown up together but apart and instantly felt a connection that we couldn’t ignore.

Where to Propose in Chilmark, Massachusetts (Martha's Vineyard)

How They Asked

I told Lindsay that my aunt, who lives on MV year round, was having a large birthday party over Columbus Day weekend and that it would mean a lot to my family if we could be there. At first she was reluctant to take a day off at work as she was narrowing in on the last of her vacation days but I was persistent and she finally agreed. It was so hard for me to hold myself back from shaking her and saying “Trust me, it will be worth it!”

We arrived Friday afternoon and I convinced her that we should get ready for the party and then catch the sunset on the way to the restaurant. That entire week, the weather was forecasted to be overcast with scattered showers occurring around sunset. Just my luck! But when we got there, the bad weather had passed and we were met by the most beautiful fall evening. We headed down the stairs to the beach where we had both grown up going to. We walked for a few minutes until we got to the rock where I planned to pop the question. I began trying to remember all of the things I had meant to say but only got out a lame “I still can’t believe that we have this place in common.”

Lindsay could sense the shift in my demeanor and that was the moment she realized we weren’t on the island for my aunt Jane’s birthday! She was laughing and crying and told me to get down on one knee before I even had the chance to get the ring out of my bag! I got there eventually and she said yes.

Engagement Proposal Ideas in Chilmark, Massachusetts (Martha's Vineyard)

The interaction was hysterical and so perfectly us. I had a photographer hiding on the dunes above us and she was able to catch the whole moment! My parents had stashed a cooler with champagne and oysters behind one of the rocks earlier that evening so we took our time enjoying the rest of the sunset and snapping a few more photos.

I told her we had to leave to make our dinner reservation for two. She spent the whole car ride trying to get her parents and siblings on the phone to share the news but nobody was answering! This made more sense to her when we arrived at the restaurant and she saw both of our families sitting at the table together. We both still can’t believe that I was able to pull it off!

Special Thanks

Randi Baird
 | Photographer