Bayfield Summertime Proposal

Many couples, families and friends plan trips to Bayfield every year. Whether you’re a first timer or you travel here every summer, the Bayfield area is a perfect destination for your getaway. What better way to propose to your sweetie than surprising them during your vacation!

Matt and Jenn live in Milwaukee and planned a summertime trip up with their closest friends. Jenn had no clue that Matt had another reason for their trip- to propose to her! We spoke with Jenn all about their trip and proposal, we hope you enjoy it!

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

Matt and I met in 2010 at Valparaiso University in Indiana. I was a freshman in college at Carroll University in Wisconsin and took the train through Chicago to visit a friend that ended up being in the same fraternity as Matt. Matt was so sweet, he offered me his coat when I was cold and (reluctantly) watched Friends with me. As they say, the rest is history. Matt graduated in 2012 and moved to Milwaukee so we could begin our forever together.

What made you choose Bayfield for your trip?
This is a fun story. So we were sitting in one of our favorite Milwaukee bars with Matt’s childhood friend Pat and his wife Meghan planning out our summer. It was the dead of winter and we wanted to road trip somewhere fun! We planned a trip to Bayfield to kayak the Apostle Islands. The weekend was all set in July, I was in charge of the playlist (bad idea), and we were excited. Somewhere between that January weekend and July, unbeknownst to me, Matt decided to bring a ring!

Tell us about your Bayfield trip and your proposal!
Early one Friday morning in July we picked up our friends, packed the car, grabbed coffee and set out north! Even just the road trip up was a blast as we climbed further and further north and made note off all the gorgeous scenery and local color.

Emily, of Lace & Brass Events, is a long time friend of Matt so he reached out and consulted with her on best places to stay, eat, things to do, candy shops to eat everything at, etc. She was instrumental in not only planning a wonderful vacation getaway but also a beautiful proposal!

So we arrive to the perfect Winfield Inn, settled in and met everyone for dinner. We then spent the evening walking around town a little bit and taking it all in. The next morning we jumped on the ferry to Madeline Island to meet up with our kayak guide. We set off in our kayaks and had an amazing time cruising in and out of all the caves along the shore.

After a FULL day of kayaking we were all sore, mosquito bitten, sunburnt- really in a romantic place as you can imagine. On the way back to our rooms, I mentioned that I was planning to wear jeans to dinner instead of the dress I brought. Meghan, knowing what was about to happen exclaimed “NO!” and politely but persistently asked that I change my mind (in hindsight I am so glad she did!). We had a great dinner at The Pier, right in the heart of downtown looking over Lake Superior. As the sun was setting with pinks and oranges bouncing off the lake and we were enjoying our after dinner drinks, Matt began telling me how much he loved his life with me in it. Being completely unaware of what was actually happening, I started to reciprocate my feelings and explain how much I loved him too. Later, come to find out, Pat was ready to kick me under the table and let me know this was not a two sided conversation…

Remember that Matt’s legs are terribly sunburnt from sitting in a kayak but he continues talking and before I know it he is down on one knee with a ring extended out to me asking me to marry him. I was so surprised, I looked at him and all I could say was “SHUT UP!”

Once I gained a slight amount of composure, I said yes, of course! Our friends cheered, the nearby tables realized what was happening and congratulated us, and our amazing waitress brought us a dessert to celebrate. I was still in shock with everything but it was the perfect proposal.

After dinner we continued to walk around town and just enjoy our engagement. All of the cute shops were fun to walk through and the owners were excited to hear our news. My favorite stop was The Candy Shoppe where I picked out a ring pop to enjoy alongside my new ring! Still being a little shaky from the nights events, I actually ended up knocking over a box of candy. As I was picking it all up, Matt proudly exclaimed that it was ok, I could do what I want because we were getting married!!

After the sun set completely it was time to let EVERYONE know! Opening the door to our room, we saw the most beautiful flowers and champagne that Emily arranged with Winfield Inn. Sitting on the porch with that bottle of champagne, cigars and our friends, we alternated calling everyone that needed to know. It was a beautiful night with the moon shining over the trees. A great way to end a perfect day!

The next morning, still elated from the day before, we packed up everything and met Emily and family in town for brunch at The Egg Toss. We enjoyed some celebratory mimosas and continued our stroll through the town’s stores. After our thanks and goodbyes, we set off down the road back to Milwaukee, nearly planning the entire wedding in the car on our way home.

Are there any recommendations you have for someone looking to propose in the Bayfield area?
Plan your trip when that January cabin fever is really setting in. It’s nice to just unplug for a weekend, enjoy the great outdoors and experience a new area. What’s so fun about Bayfield is the natural lake town feel. Everyone is so kind and laid back and the views of Lake Superior are amazing. A never ending supply of outdoor adventuring right at your finger tips. For the actual “big question,” Matt has said it was so helpful having Emily with Lace & Brass Events recommend places to go and thing to do during the trip so the happy couple can focus on one another.


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

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