A Madeline Island Proposal

How do you plan a surprise proposal without your sweetheart catching on? Pop the question on vacation, of course! It seems that every year we hear about a handful of lucky couples who get engaged over Apple Festival weekend here in Bayfield. It is, after all, the perfect opportunity to come visit this beautiful area with your significant other, family and friends. What better time to get down on one knee than on a crisp fall day with apple orchards, wineries, and the beautiful Lake Superior all around you?

Read all about Tyler and Delaney’s proposal that happened while they were visiting Bayfield and Madeline Island the weekend of Apple Festival!


Tell us a little bit about yourselves and how you met.

My fiance, Tyler and I met a long time ago in middle school. We started dating during our junior year of high school, and were fortunate enough to both decide to go to the University of Minnesota- Twin Cities campus after we graduated. We continued dating throughout our college careers. We both graduated in 2015, and he accepted a job as an engineer while I moved on to attend the College of Pharmacy at the U.

What made Tyler choose this area?

My parents have gone camping on Madeline Island during Apple Fest weekend with some of their friends and family every year since before I was born- I think it’s been about 28 years. I had never been to Bayfield or Madeline Island, so Tyler and I thought it would be fun to go with them one year. Although I was a bit hesitant about going due to the weather (it’s cold in October!), Tyler was adamant we go so I gladly followed. He had been to Madeline Island before as his relatives have a cabin on it, so he knew it would be a wonderful spot for a proposal. 

Tell us about your Bayfield/Madeline Island trip and your proposal!

We went to Bayfield on the Saturday of Apple Fest weekend and wandered the festival during the day, eating, drinking, and seeing the sights with my family and friends. After a bit, we decided to get on the ferry and head over to the island. We made a stop by Tom’s Burned Down Cafe and then Tyler and I went off on our own to explore the island.

After walking a while, we came across a beach and went and sat on a bench to watch the setting sun. He reached into his pocket, got down on one knee, and said the words I’d been waiting to hear for about 6 years: “Delaney, will you marry me?”

We then went to our campsite to celebrate with my family. Tyler had told my parents of his plan a few weeks earlier, so they were prepared with champagne to pop as we celebrated our engagement all night!

Are there any recommendations you have for someone looking to propose in the Bayfield area?

I certainly recommend proposing by the water, it’s so beautiful and adds that “special something” to a proposal. It also adds a little extra romance to have plans as a getaway, so that some time can be spent just the two of you before the overwhelming amount of well wishes are sent from friends and family once you make your announcement. Of course, I’m partial to planning a camping trip for the proposal, but that’s just because it was my fairytale come true!

If you are planning a Bayfield proposal, wedding or honeymoon take a look at our resources and inspiration page!


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