Sunset in Sister Bay, WI
Travel & Activities

A Weekend in Door County: What to See & Do

Wondering what to do with the last few weeks of summer? Plan a trip to Door County!

With mask mandates and physical distancing in place, things will definitely be a bit different than usual. But isn’t pretty much everything right now? It doesn’t change the fact that Door County is my happy place. And definitely worth the drive.

Door County is an easy 3 1/2 hour drive from Madison and absolutely feels like a vacation. We try to go once a year for a long weekend – with or without the kiddo.

I first got to experience Door County when I was working for the Alumni Association many moons ago. As part of my role there, I got to host a “Murder Mystery Weekend” for UW alumni at Björklunden, a retreat center owned by Lawrence University just outside of Bailey’s Harbor.

My mom came along for the weekend, which was fairly structured since it was an alumni learning program. However, when we did get a bit of free time, we ventured out with absolutely no idea where to go. During our first real break in the program, we jumped in the car and just started driving. We stumbled upon Stone’s Throw Winery on the drive and did a little wine tasting before heading back to Björklunden.

In all honesty, that is about all we got to do on that trip. However, I knew just from driving around and that quick visit to the winery that I absolutely wanted to return to the region. With more time to explore on the next visit.

I did return a few years later for a friend’s wedding at Gordon Lodge, which is on the same side of the peninsula as Björklunden, that time with my now husband. Since we were there for a wedding, we primarily stayed on the property, which was adorable. We had our own little cottage, instead of a standard hotel room, and the resort was right on the water.

However, the morning after the wedding, we went into town for the Bailey’s Harbor Farmer’s Market. It doesn’t hold a candle to the Dane County Farmer’s Market, but was lovely and quaint in it’s own right. It is quite small, since Bailey’s Harbor is also a small town. Yet offers a nice assortment of both crafts and farm goods for sale. One weekend per year, they also hold an antique car show in conjunction with the market. Which also just so happened to be that weekend. So, we checked out the old cars as well.

On the drive back to Madison, my husband and I agreed that we wanted to go back the following year. This time for a long weekend on the other side of the peninsula, with no plans but to explore.

We landed on Memorial Day weekend, when we knew shops and restaurants would reopen for the summer. However, still before “peak” season in Door County. So we were hoping the traffic and crowds wouldn’t be too bad.

I took to VRBO to look for a vacation rental and found this adorable little cottage in Ephraim. Turns out it was in someone’s backyard, which isn’t uncommon in Door County. It was walking distance to the beach and just the right size for the two of us. It was very close to the Old Post Office Restaurant where we went for our very first fish boil as well.

Since that visit, we’ve returned to Door County almost every Memorial Day weekend since. We’ve taken our son with us a couple of times as well, and it is always a very good time.

For my 40th birthday, my husband even planned a surprise weekend trip to Door County. He rented an entire house up in Gills Rock at the tip of the peninsula just for the two of us. We went back for our 7th anniversary nine months later as well. That’s how much we like it there!

Now that I’ve been to Door County at least 10 times, I have discovered many of it’s hidden gems, along with well-known favorites. We have a list of things we love to do when we are in the area. Yet we never seem to have enough time to do them all on one visit.

If you are looking for a lovely getaway somewhat close to home, here are my recommendations for what to see and do in Door County:

Where to Stay

We have gone back to VRBO several times to book our Door County vacations. While I am not a fan of the service fee increases they’ve implemented over the years, it is still a reliable source for vacation rentals in the area. Now, with the addition of AirBnB, there are even more options to book.

Since Door County is comprised of several small towns, we try to stay in a different place each time. Each rental thus far has been great. However, the type of rental you might look for is entirely dependent on who you are going with. Whether you are going as a couple, with friends, or your whole family, you’ll have different needs for each visit.

For Couples

In addition to the little cottage I mentioned above in Ephraim, the TreeHouse at Plum Bottom was one of our favs. It’s a one bedroom apartment above an art gallery located outside of Egg Harbor and was nestled inland, about half way from either side of the Peninsula.

The property was all ours after the gallery closed for the night, so it was also very private and secluded. I loved the lighted path that brought us to our rental. Along with falling to sleep to the sound of the babbling brook fountain below our bedroom window. It definitely felt like a retreat.

For Small Families

For small families like ours with just one child, particularly while they are still little, we really loved Applewood Cottage, also outside of Egg Harbor. This little one-bedroom cottage was on a 10-acre farm with lots of trails. The owner told us to feel free to walk the grounds and enjoy the full property, which we did.

Applewood Cottage in Egg Harbor, WI
Applewood Cottage in Egg Harbor

The cottage had an outdoor fire pit and picnic table for us to enjoy meals al fresco as well. It was the perfect size for our little family. Though it was just one bedroom, we set up my son’s pack and play in our room. He was not quite two at the time. Now that he is a little older, it wouldn’t work so well. This place would also be lovely for a couple too, however.

Even better for families perhaps was The Hilltop Inn in Fish Creek, where we stayed when my son was almost one. We rented a two bedroom condo there, which was spread out over two floors/townhouse style.

My husband and I had our own room and set up the kiddo’s pack and play in the room across the hall from ours. It was nice to be able to hang out just the two of us downstairs after the kiddo was asleep. Because we didn’t have to worry about waking him up.

The condo also had a full kitchen, dining area, and living room. So we could order in food, or easily eat leftovers. Thus, saving a little cash along the way.

This place was right off the main highway, but further removed from the downtown traffic. It also had a small outdoor pool, which is a nice amenity for the warmer months.

For Larger Families

For families with more than one child, or if sharing a place with another small family, I would recommend this place on the lake in Gills Rock called Teskie’s Cottage which sleeps up to 6. It has five bedrooms, so obviously more than we needed for just us. However, it worked really well for a couple’s getaway too.

Given the ample space with a living room, den, and eat-in kitchen, along with the fire pit out back on the water, this is a great spot regardless of group size. The owner even left us a jar of fresh maple syrup upon arrival. Which was just the type of nice little touch you get in a place like Door County.

Teskie’s Cottage is also very close to Charlie’s Smokehouse, which is one local establishment we always make the drive up to the tip for, to get some fresh smoked salmon, trout, fish dip and crackers that we snack on throughout our stay in the area. That definitely worked in our favor. Though it is pretty far up the peninsula. So if you stay here, just know that you will spend a good part of your time driving if you decide to explore outside of Gills Rock. Though we tend to do that often in DC, just for the scenic drives anyways.

What to Eat

Having visited annually for the past 10 years, we’ve definitely compiled a list of favorite eats in the area. There are so many great options to chose from that it’s hard to go wrong. However, we have had a few disappointing meals in Door County. Therefore, we tend to stick to our favs since they are consistently good – along with trying at least one new place per visit.


Grasse’s Grill in Sister Bay is a new spot we added to the list after our last visit to Door County. When we went to get the obligatory fish dip and trout at Charlie’s, we asked the gal working there what her favorite restaurant was in the area. She immediately responded “Grasse’s Grill” without even thinking twice about the answer. After she said it with such conviction, we knew we had to give it a try.

When we arrived, we realized we had stopped at Grasse’s a few years back for cherry mimosas. Though we never ate a meal there. Breakfast is the way to go though, as we both had phenomenal dishes enjoyed al fresco on their side patio.

The Blue Horse Beach Cafe in Fish Creek is another breakfast standard for us in Door County. They have THE BEST cup of coffee in the area. Trust me on this one. I searched for years.

We love the Blue Horse for their simple breakfast sandwiches, best enjoyed on the screened in front porch overlooking the water in Fish Creek. But seriously. After years of disappointing coffee throughout Door County, when I had my first latte at the Blue Horse, I nearly cried tears of joy. Grab a pound or two of beans to take home too. You won’t be disappointed.

Good Eggs in Ephraim is also a great spot for a simple, delicious, and very filling wrap. That is all they do. Breakfast wraps made to order, along with fresh fruit smoothies. There is always a wait, since it is a pretty popular and very small spot. Be prepared to sit and wait for up to an hour, and also know that there is no indoor seating.

The Village Cafe in Egg Harbor is the perfect breakfast spot if you are looking to sit down with a bigger group, with a wider variety of menu items certain to please a crowd. The fun decor, which is also for sale, makes for something interesting to look at while you wait for your food. During one visit, they even had a clearance table with some items for sale out front. The shopper in me found a cute pirate raincoat for the kiddo complete with an eye-patch for $15.

Brunch at the Wickman House
Anniversary brunch at Wickman House in Ellison Bay

If you are looking for a fancier spot to do brunch or celebrate a special occasion, the Door County Cherry Stuffed French Toast at The White Gull Inn in Fish Creek is a must-try. However, the rotating, seasonal menu at the very fancy Wickman House is also worth the trip to Ellison Bay. We celebrated our anniversary with brunch at the Wickman House last year and it was delightful. The grounds are really beautiful and they have a gazebo you can hang out in, along with some yard games to play while you wait as well.


In all honesty, we don’t tend to eat lunch very often in Door County because brunch is our thing. By the time we eat a late brunch, we don’t generally need lunch too. When we get hungry in the afternoon, that’s where our snacks from Charlie’s Smokehouse usually come into play.

However, we of course have had a few lunches here and there in Door County. Most of the breakfast or dinner spots we tend to frequent offer lunch items as well.

The Cookery in Fish Creek is a great spot for any meal, particularly if you sit out on the front patio to people watch. I had a really delightful salad with Door County cherries the last time we were there. DC cherries are a big menu feature in most restaurants in the area.

If you like barbecue, Casey’s BBQ & Smokehouse in Egg Harbor is also a great lunch choice. My husband LOVES smoked meat, so he is always game for some BBQ! Casey’s offers a great array of sandwiches and platters, along with bar type appetizers. You can also order bulk meat to go to feed up to 25 people if you want to take some back to your rental.

Peddle bike at PC Junction
Pedal car at PC Junction in Bailey’s Harbor

PC Junction in Bailey’s Harbor is a great place for kids! Not only do they have a very kid-friendly menu, but your lunch/dinner is also served by train car if you sit at the bar. They have a large outdoor playground area with these little pedal cars that we had so much fun riding around too! Plan to stay awhile if you drive out there. Not just for lunch, but for the playing that will surely ensue after!


Wild Tomato Wood-Fired Pizza is a MUST in Door County. They added an additional location in Sister Bay, along with the original in Fish Creek a few years ago. There is something to be said for the original though. It is smaller than the new location, so there is always a wait. But I love sitting on the outdoor patio in front of the restaurant, which is strung with little lights that go on when it gets dark. You can dine in or carry out at either location. And they even have a separate carry out building in the back at the original location.

Last time we were in Door County though we ate at the new location in Sister Bay. They definitely have a larger seating capacity and if you are already staying in Sister Bay, it’s great that there is another option since Wild Tomato is so popular.

They have a rotating pizza special that serves as a fundraiser for a local organization. So we usually order one of those, along with our favorite the “Fun Guy”. If you like mushrooms, you have GOTTA try it. It’s pizza perfection in my opinion.

For dinner one night, you HAVE to try a good old fashioned Door County Fish Boil though. It’s a tradition! And there are several restaurants in the area that do them, including the White Gull Inn, Pelletier’s and the Old Post Office Restaurant. Our favorite for a fish boil is the Old Post Office in Ephraim, which heads up, is a dry town. So, you cannot order any alcohol with your meal. In my mind, it’s not necessary though in order to enjoy a dinner out.

A fish boil is essentially white fish, potatoes, and onions boiled together in a pot with salt. Part of the fun of a fish boil is watching the “Boil Master” man the gigantic pot they use to boil your meal. Generally, everyone stands outside and watches until the fish “boils over” which means it’s ready to serve. Then you all go inside and sit down and everyone is served the exact same meal.

Fish boils are usually a flat rate price and come with a side of coleslaw and a slice of Door County cherry pie. At the Old Post Office you can pay a small up-charge to have your pie served à la mode with a scoop of traditional vanilla ice cream on top too. It is worth it.

You obviously have to like fish in order to go to a fish boil. But I just think they are fun. And the meal is surprisingly tasty for being so simple.

Regardless of which location you choose, you do have to make a reservation as they tend to book up. Plus, fish boils are only available on certain nights of the week, usually Friday and Saturday. So, check the web sites for more info.

What to Do

One of the many great things about Door County is that there is SO MUCH TO DO in the area! While many of the annual events may be cancelled this year, there are still plenty of places to go and to explore.

State & County Parks

There are several state and county parks in Door County and we have explored many of them over the years. Peninsula State Park is one of the most popular, which means it is also usually pretty busy. Camping reservations for Peninsula book out months in advance, so plan accordingly if you’d prefer to camp rather than rent.

Rock Island State Park is also an amazing place to camp. However, you have to take two ferrys to get there. And you can’t bring your car. Sadly, it is closed for the remainder of the year due to COVID. So you’ll have to put this on your list for a later date once we have gotten this virus under control. My husband took me there years ago to celebrate our anniversary and it was quite an adventure to say the least!

View from Rock Island
View from Rock Island

If you are hard core campers, you can also camp at Newport State Park, which is a very nice park to hike around and explore. They offer backpack only camping sites, which you have to walk up and reserve. So this probably wouldn’t work well for families who need to plan in advance. However, I would recommend a day trip to take a nice long walk along the shore. It is usually much quieter than Peninsula, so a bit more relaxing too. It’s a “Dark Sky Park” as well, which we haven’t taken advantage of, but you might want to check out!

Ellison Bluff State Natural Area is one of the first places we went hiking in Door County. It’s right off the main highway in Ellison Bay and offers some pretty amazing views of Lake Michigan, like most of the county. Put on some good hiking shoes so you can hike down the bluff to the water.

We like to disc golf together as a couple, so on one trip with just the two of us we went to play a round at Sugar Creek County Park in Brussels. The 18-hole course is really wooded, so it was actually a pretty hilarious round. I kept throwing my disc into trees and losing them in the woods. But we still had a really good time! This park is pretty far off the beaten path though, so plan on extra time. We stopped there on our drive into the county vs. making a day trip to drive back down after we were already there.


Clothing and Accessories

Shopping always has and always will be one of my most favorite pastimes. And Door County has many amazing boutiques and small businesses to support!

However, shopping in Door County is not cheap. So, be prepared to spend a little more than you usually would. However, you will find some truly unique pieces you can’t get here in Madison. Plus, you’ll be supporting a small local business, which is part of what makes Door County so special.

I will say one bonus of the pandemic, is that many of the small businesses we know and love who did not have robust online presences prior to COVID-19, have stepped up their e-commerce and web sites. So, even if you aren’t able to take a trip up to Door County this year, you can now shop many of these stores online!

The Patricia Shoppe in Egg Harbor is my hands-down favorite boutique in the area. It’s run by a woman named Erin who is about the same age as me and is also a Mom. She is amazing at remembering details. For example, she’ll remember exactly what I bought the year before. And recommend things that I might like based on previous purchases as soon as I walk in the door. I love that sort of highly personalized service that makes you feel like a valued customer.

Patricia Shoppe is a women’s clothing and accessories boutique that carries hard to find brands like Effie’s Heart and XCVI. They used to have a shop here in Madison right off of State Street, along with a third location in Whitefish Bay too. However, both of those stores have closed down, so the flagship store is all that remains.

I generally make a stop to Fred & Co. whenever we are in Fish Creek as well. Fred & Co. is another women’s clothing boutique that has fabulous, on-trend styles from brands I love, like Free People and Kut from the Kloth. This is a small shop right on the main drag, so it is really easy to find.

The Spot in Sister Bay is also a fun little stop whenever we are in the area. They have funky clothing and accessories, along with a separate store below that features home goods. Prices at The Spot are much more affordable than some of the other shops in the area as well.

Ecology Sports is also worth a stop when in Sister Bay because they have something for the entire family. This is more of an outdoorsy shop for folks that like to hike, kayak, and fish. However, they carry men’s, women’s, and children’s clothing and accessories, from high quality brands like Patagonia and Sorel. I also found two amazing Woolrich beach towels on clearance there for $25/each last time. They served as anniversary gifts for me and the Hubs that year.

Food/Grocery Items

I’ve already mentioned Charlie’s Smokehouse in Ellison Bay as a must-stop for all things seafood. We always grab a pound or two of smoked fish along with fish dip to eat while in Door County, plus with one of each to bring home. I honestly cannot imagine a trip to Door County without stopping here for some snacks.

Charlie's Smokehouse
Charlie’s Smokehouse in Ellison Bay

We also enjoy visiting The Barrel Room in Fish Creek to stock up on food stuffs for both our stay and to bring back to Madison. They have a wonderful selection of wine, cheese, Fat Louie’s olive oil and balsamic vinegar, fudge and other gourmet snacks. They carry Door Peninsula Winery wines there and will do free tastings as well! (Not sure if they are still doing this during the pandemic though).

Fat Louie’s has their own store in Egg Harbor as well. They usually run a special where if you buy 5 bottles of olive oil or balsamic, you get one free. So, we always stock up!

Wood Orchard Market is great for all things Door County cherry. This is where we usually stop for cherry donuts, dried tart cherries, and tart cherry juice concentrate (TIP: tart cherry juice has naturally occurring melatonin! If you have a rough sleeper, this can help). There are several farm markets in the area, but this one tends to be our favorite.


Door County is also known for the wineries and there are at least 7 or 8 to choose from in the area. Back in our childless days, we tried to hit them all in one visit, since wine tastings are offered at each of them (most for free). We would stop and try the wine and buy a bottle at each location. A few for drinking over the long weekend, plus a few to bring back home.

Door Peninsula Winery in Sturgeon Bay has the most extensive menu and is now co-located with the Door County Distillery. So, you can kill two birds with one stone if needed. They have a large selection of sweet berry wines, so if that’s not your thing, you may appreciate one of the other wineries more. However, we really like the Cranbernet and Peninsula Red, so we do usually stop here once per visit.

Just a few miles up the road from there, you will find Simon Creek Vineyard, which is nestled on a beautiful hillside. They play live music outdoors on the back patio every Sunday. Bring a blanket and buy some cheese and crackers inside the winery. Then spread out on the lawn to drink a glass (or two) and take in the tunes. It is one of the most perfect ways to spend a Sunday afternoon.

Be sure to check out Island Orchard Cider in Ellison Bay as well. While not a winery, but instead a cider mill, this is much smaller than the other wineries. You can buy a flight and sit out on the patio to watch the world go by without dealing with the crowds you might find elsewhere. I like all things lavender and the Apple Lavender Cider is worth the trip in and of itself. You can find Island Orchard in many different stores in Madison too if you want a taste of Door County a bit closer to home.

Cider Flight at Island Orchard
Cider flight at Island Orchard

If you find yourself on the other side of the peninsula, a visit to Door County Brewing Co. in Bailey’s Harbor is definitely in order. They have a big back patio as well, along with lawn games like corn hole out front. So, it’s a great way to pass some time and enjoy the outdoors along with your beer. A flight is the way to go here as well, so you can try several varieties at once. They frequently have live music here too.

These are just a few of my many favorite things to see and do in Door County. I would love to hear yours as well! What did I miss? Or what do I need to add to the list for our next visit? Please share in the comments below.

Fish Creek Harbor
Fish Creek Harbor

2 thoughts on “A Weekend in Door County: What to See & Do

    1. Sorry I missed your comment earlier! I’d love to experience Cave Point Paddle and Pedal first before adding it to the post. I’ve actually never been to Cave Point in all my visits to Door County! Can you believe that?! We will hopefully be up again in May or June and could check you out then!

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