A few weeks ago I had the pleasure of going on a brand trip with Lands’ End to Door County, Wisconsin. During the trip, we traveled in a quintessential Door County Trolley to explore the peninsula’s must-see attractions. It was truly such an amazing experience! The entire trip was very much a “pinch me” moment. Even as recently as a year ago, I never would have imagined being presented with such a wonderful opportunity. Lands’ End has been on my list of favorite brands for as long as I can remember. I grew up wearing their classic clothing. And after hearing family and friends say the most wonderful things about Door County, I couldn’t wait to visit the area!
I am happy to report that this Wisconsin peninsula far surpassed my expectations, and I can’t wait to go back someday. It would be the perfect destination for a family vacation! Each morning of the trip, we hopped on our Door County Trolley and explored the beautiful sites, tasted the most delicious foods, and participated in fun adventures. Today I’m excited to share my complete travel guide, highlighting all of the special attractions in Door County.
Thank you to Lands’ End for sponsoring this post! It was such a joy to have this opportunity, and I am very grateful. All content shared in this post features my honest thoughts and personal opinions.
Door County, Wisconsin
My family and I are always looking for vacation destinations in the Midwest. There aren’t a ton of fantastic options within driving distance. We usually end up going to the Ozarks or flying somewhere warm like Florida. However, I’ve always heard great things about Door County, Wisconsin, and it has been on my destination wish list for quite a while. So when Lands’ End reached out asking if I’d be interested in visiting the area on a brand trip, the answer was an immediate “yes”!
Door County Trolley Views
Door County is often described as “the Cape Cod of the Midwest” and I think this is a very accurate description! I’ve visited Cape Cod twice in the last few years and there are a lot of similarities between the two locations. We were able to visit a lot of incredible destinations from our Door County Trolley each day. Many attractions that are popular in Cape Cod can also be found in Door County – stunning beaches, gorgeous lighthouses, picturesque small towns, and unique shopping options.
I’m not sure I could choose a favorite between the two destinations, as I think both are worth visiting. I’ve never visited Cape Cod in the fall (only in the summer and spring); however, I can honestly say it would be very hard to beat Door County’s autumnal beauty!
Door County Trolley Adventures: A Travel Guide
If you can’t tell, I’m slightly obsessed with this destination, and I cannot encourage you to visit it enough! Therefore, I wanted to put together a complete travel guide highlighting everything from how to get there, where to stay, and which Door County Trolley stops are must-see attractions.
How to Get to Door County
First up, let’s discuss how to get to Door County. For this trip, I flew out of the Peoria, Illinois airport and into Green Bay’s Austin Straubel Airport. I had a short layover in Chicago, but I chose to fly from Peoria because I always prefer to leave from a small, local airport. It’s so much easier than dealing with traffic, long lines, etc. Upon arrival in Green Bay, I took a shuttle to Door County. It was roughly an hour-and-a-half drive from the airport to our lodge.
If I were to go back, I would drive instead of flying. It is under a seven-hour drive from our home and between driving to and from the airports and the flight itself, I really didn’t save any time by flying. Once we arrived at the final destination, we traveled via this Door County Trolley company, which was wonderful!
Where to Stay
For this trip, we stayed at Gordon Lodge, which had incredible views of the bay. Each morning I opened the door to my room’s back patio and took in the gorgeous sunrise on the water. Gordon Lodge had different accommodation options ranging from single rooms to entire houses, which would be great for families! I spoke to a few locals during the trip who also recommended checking out Airbnb for additional Door County lodging options.
Door County Trolley Attractions
Okay, now for the really fun part – the best attractions to visit during a Door County Trolley adventure! Destination Door County (the local tourism bureau) and Lands’ End did an excellent job creating an itinerary that ensured we were able to visit all of the best spots. We crammed a lot of Door County attractions and activities into two days. It was a bit exhausting, but totally worth it! Here’s a rundown of my favorite stops.
1. Cana Island Lighthouse
I was surprised to learn that this midwestern destination has 11 lighthouses! Our Door County trolley made a stop at the peninsula’s most iconic lighthouse, Cana Island. Built in 1869, you can take a haywagon ride across rocks and sand to get to the island, or you can simply walk. The entire area was beautiful and while I didn’t climb the 97 stairs to the top, I would do so if I returned. According to my friend Lauren, the view was breathtaking!
2. Lautenbach’s Orchard Country Winery & Market
Lautenbach’s Orchard Country Winery & Market was one of my favorite Door County Trolley stops. The grounds were gorgeous, full of rows and rows of fresh fruit. There was also a wonderful market at the orchard with tons of fruit spreads, home decor, and of course, apple cider donuts! They even had a wine and cider tasting area, which looked like so much fun. I picked up a special book as a souvenir to take home to Millie!
3. Ridges Sanctuary
Ridges Sanctuary is a beautiful nature preserve that has walking paths, hiking trails, and a nature center. We spent some time walking the trail back to the range lights. It was such a calm and peaceful area. Definitely worth visiting if you’re a fan of hiking and nature!
4. Sailboat Cruise
I thoroughly enjoyed every stop on our Door County Trolley adventure, but I think if I had to choose my overall favorite it would be the sailboat cruise we took in Sister Bay. This was my first time sailing and it was such a magical experience. We sailed on the Edith Becker boat, which was such a classic, and our boat’s captain and staff were incredible! It was such a special way to see this area and I highly recommend booking a tour with Sail Door County if you ever visit.
5. Peninsula State Park
This was the first attraction we visited and it definitely kicked the trip off with a bang! Peninsula State Park had so many options to explore – campsites, a golf course, bike trails, a beach, a lighthouse, and more. The highlight of this stop was walking up Eagle Tower and taking in the panoramic views of the park and islands.
6. Downtown Egg Harbor
Our Door County Trolley made a stop at Egg Harbor for lunch and shopping. It was such a fun little area! There were a lot of cute shops that I was eager to explore, but unfortunately, we ran out of time after lunch. I will definitely be returning to do some shopping at the boutiques the next time I visit! They also have a distillery, winery, and many delicious dining options. One tip…be sure to check the day and hours of operation for shops in each area of Door County. There were quite a few stores that were closed on certain days of the week.
7. Downtown Sister Bay
Another wonderful area for shopping, dining, and exploring is downtown Sister Bay. We were able to wander around this area after our Sailboat Cruise and it was so much fun! Similar to Egg Harbor, Sister Bay is full of shops, restaurants, and unique activities. One of the highlights of this stop was watching goats graze on the rooftop at Al Johnson’s. Yes, goats were on the roof!
8. Door County Fish Boil
Before this trip, I had never heard of a fish boil. But apparently, these are a big deal in Door County, which meant experiencing one was a must! We had the pleasure of enjoying a traditional Door County fish boil at The White Gull Inn. This Inn is a beautiful historic bed and breakfast – one that I would love to stay at someday! The fish boil featured Lake Michigan whitefish caught freshly by local fishermen and cooked outside over an open fire. Admittedly, I opted for chicken over fish, but the entertainment was great, and the food was delicious. They even had a dairy-free cherry pie for dessert!
9. Anderson Dock
Last, but not least, our Door County Trolley made a stop at Anderson Dock. This is a fun and unique place where you can paint your name (or whatever you’d like) on the walls of a dockside warehouse. I think this would be such a great stop for newlyweds or for families with children. Be sure to also visit Wilson’s Ice Cream, an old-fashioned ice cream shop, while you’re in the area!
Where to Eat in Door County
I have no doubt there is an endless list of wonderful restaurants throughout this Wisconsin peninsula. However, our trip was only two and a half days long, so I was only able to experience a few of them. The ones I did dine at were delicious! Here’s a quick overview of the foods I most enjoyed during our Door County Trolley adventures.
Best Pizza
Pizza is quite possibly my favorite food, so I love trying out new pizzerias when traveling. Pizza Bros was in the same building as One Barrel Brewery, and it was such a neat, laid-back environment. The wood fire pizza was made from scratch and it was so good! I would love to go back with Brent someday because I know he would enjoy this pizza and brewery combination as much as I did.
Best Ice Cream
Hands down, Door County Creamery wins the award for best ice cream with its fresh gelato made from goat’s milk! If you’ve been following along for a while, you may remember that Millie and I both have a cow’s milk intolerance. However, we can both eat goat’s milk products without any issues. The Creamery was full of specialty goat’s cheeses, soaps, gelato, and even made-to-order sandwiches!
Most Unique Dining Experience
As I previously mentioned, a traditional Door County Fish Boil is an experience you simply can’t miss! I highly recommend dining at The White Gull Inn for this meal.
Best Snack
This area of Wisconsin is known for its cherries and we saw the fruit’s products at almost every stop. I was thrilled to find these dark chocolate covered cherries, which are grown locally, have no artificial colors, and are dairy-free. They were so delicious that I instantly went back and bought a few more bags to bring home to Brent and Millie!
Best Meal
On our last night, our Door County Trolley took us to Thyme, and it was my favorite meal of the trip. I ordered salmon, and not only was it delicious, but the restaurant’s environment was wonderful. My friend Hannah ordered the fig and goat cheese flatbread and let me have a taste. I think that’s what I would order if I returned!
Fall Capsule Wardrobe
Okay, now let’s shift to what I wore while in Door County! I’m not going to lie, when Lands’ End first informed us that we would be putting together a capsule wardrobe for the trip, I was a little worried. Lightweight packing is not my strength! However, I was pleasantly surprised at how many fall outfits I was able to put together with just a few classic pieces of clothing.
This ivory cable knit sweater was the MVP of the trip (and will be for the remainder of fall). It is such a timeless piece, fits great, and the price point is excellent! I paired it will so many different outfits including layered under this green vest and draped on top of this chambray dress. This green zip-up sweater was another favorite piece, which comes in a variety of colors and patterns. I layered it on top of this camel brown striped turtleneck paired with jeans and tall boots for a quintessential fall outfit.
And you know I can’t travel without some comfy, casual pieces. I was highly impressed with these emerald green high-waisted leggings. The fit was flattering and I love that they have pockets. I paired them with a long-sleeve floral top (incredibly soft) and a matching crewneck sweatshirt. For the flight home, I draped this same sweatshirt over a navy striped top and paired it with comfy joggers. For outerwear, I layered this adorable green quilted jacket (which happens to be reversible!) on top of everything.
shop the outfits
Lands’ End Trip to Door County
I could go on and on about how wonderful our Door County Trolley adventures were. It was such a special experience from start to finish. I am forever grateful to have had the chance to work with the amazing Lands’ End team, to get to know the other talented content creators, and to experience the beauty of this Wisconsin peninsula for the first time. I truly cannot wait to return to Door County someday and share this beautiful place with my family!
