Proposing in the Winter: Bayfield Style

Interview with Becky Haller of Pinehurst Inn

August 2, 2017

A relaxing, romantic and adventurous honeymoon is exactly what Bayfield can offer newlyweds looking to get away! Pinehurst Inn is one of many beautiful Inns here in the Bayfield area- a perfect place to honeymoon! We interviewed with Becky Haller to hear all about their honeymooners and what Pinehurst Inn has to offer. Enjoy!

Tell us a little bit about yourself and Pinehurst Inn.
Mike and I purchased Pinehurst Inn in March of 2016. We made the move from Chicago to Bayfield to enjoy a slower paced life and the beauty of Lake Superior and the Bayfield area. Owning an inn allows me to cook and bake for guests, which I love to do.  The Inn is comprised of 2 buildings—the original home built in the late 1800s, which includes 5 guest rooms, and the garden house built in 2003, which includes 3 guest rooms. A 3 course breakfast and an afternoon snack is provided each day.

What makes Pinehurst Inn special for honeymooners? 
The Pinehurst Inn is located 3 miles south of downtown Bayfield on 3 ½ acres, surrounded by soaring pines and adjacent to Pike’s Creek. Couples can enjoy the peace, beauty and tranquility that the property offers, yet be just minutes away from Lake Superior and the many activities the Bayfield area has to offer.  Many of our rooms have large jetted tubs and fireplaces, and some have private decks—some of the favorite amenities of our honeymooners. We have a number of porches, a patio, and other sitting areas on the property allowing couples to find their own special spot.

What time of the year is busiest for honeymooners?
The summer is the busiest for honeymooners, which is a great time of the year for enjoying Lake Superior, Madeline Island, and all the many hiking and biking trails in the area.

What activities do you typically recommend to honeymooners who stay with you?
It all depends on the couple’s interest.  Many of our honeymooners have enjoyed kayaking to the sea caves, exploring Madeline Island, taking a private boat tour to some of the Apostle Islands, hiking the nearby trails, and visiting the local wineries, orchards and farms.

What recommendations do you have for couples looking to honeymoon in Bayfield?
Make sure they schedule any kayaking or small boat tours ahead of time so they are not disappointed if they cannot take the tour they want, but don’t over schedule your trip. Most couples enjoy some down time and the Pinehurst Inn is ideal for rest, relaxation and connecting with one another.

To learn more about Pinehurst Inn visit their website and Facebook page.

Bayfield Summertime Proposal

March 31, 2017

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!

A Madeline Island Proposal

February 8, 2017

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!