Inn at Perry Cabin Surprise Proposal | Madeline & Kenneth



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Engagement Session, Portraits, Proposal, Weddings

Kenneth and Madeline’s Mother contacted me about 3-4 weeks before the big day. They wanted to plan a surprise proposal at St. Michael’s famed Inn at Perry Cabin (about 20 minutes from Easton, Maryland). The trick is that Madeline has been throwing some hints at Kenneth so the challenge was how to get her to the Inn at Perry Cabin without her suspecting anything. She saw the Inn at Perry Cabin in a magazine a year ago and had been hoping to visit.

After a few meetings we settled on a plan. Kenneth told her they were meeting a friend for dinner at the Inn at Perry Cabin. He had his friend send text messages to confirm the dinner and even had the friend call 10 minutes before 5:45pm so say he was running late and that they should walk the grounds until they arrived. What Madeline didn’t know is that I was sitting in those white adirondacks, with cameras in my lap waiting for Ken to make his way to the spot we picked out.

Even from a distance I heard her exclaim “ARE YOU SERIOUS!” It was such a beautiful moment. They shared a hug as their dog, Senator sniffed around wondering why everyone was so excited. Madeline’s beautiful ring is such a testament to Kenneth’s love and attention to detail. The custom ring a fancy yellow radiant cut diamond with brilliant round cut diamonds in the halo and band. They are French pavé set in platinum. The ring was inspired by Madeline’s mother’s ring which was also a yellow diamond.

We strolled around the grounds of the Inn, letting the moment sink in. One of the best things about the Inn at Perry Cabin is the range of their property-nantucket grounds, romantic gardens that gives way to a view of the water. The Inn at Perry Cabin also has a fleet of sailboats and yachts you can charter and Kenneth had arranged for a romantic private cruise aboard one of the yachts. It may have been grey on shore but as we got further out on the bay, the setting sun turned the sky to soft pastels. They shared champagne, chocolate strawberries and puppy cuddles as the the news settled in- they are engaged! It was a perfectly planned proposal, but oh Kenneth wasn’t quite done yet. Their romantic dinner would conclude with an evening spent at the Inn!

Congratulations Kenneth and Madeline (and Senator)!

Vendor Credits

Photography | Silver Orchard Creative
Venue | Inn at Perry Cabin
Charter | Down Easter Yacht Charters
Rings | Harry Merrill & Son Jewelers

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