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February 17, 2023

The Perfect Weekend in Sister Bay, WI

Door County

A trip to Door County is one of the most perfect getaways from Milwaukee, Chicago, or Minneapolis.  Just a few hour drive and you’ll escape the city for a beautiful landscape, epic sunset over Lake Michigan, amazing 5-star restaurants, local wineries, and so many adventurous things to do. Door County will refresh your soul and if you’ve never been, I promise once you’ve experienced it for yourself, it will be a place you return to over and over again.

Drive up the coast of the Door County peninsula on Hwy 42 and you’ll come across several harborside villages from Egg Harbor to Fish Creek, Ephraim to Sister Bay, and all the way up to Ellison Bay and the tip: Gills Rock. All of these places are lovely in their own way and offer a unique personality and things to do.

In this post, we put together a curated weekend plan that will give you exactly what you need to know for how to spend a weekend in Sister Bay and a perfect few days in Door County.

Its name comes from the view of two twin islands offshore, Sister Bay is one of the most popular villages in Door County, and for good reason. With over a mile of beachfront to enjoy at Waterfront Park so there’s no concern about overcrowding and with tips to get reservations at the best spots in this post, you’ll be prepared to enjoy this special place.

How to spend 3 days in Sister Bay, Wisconsin

Where to stay for a weekend in Sister Bay

There’s nothing like heading to the cabin when it comes to heading to Door County and we can think of no better cozy weekend vibes than an A-frame. Our pick: Rowley’s A-frame in Sister Bay.

Relax by a bon fire on the beach, swim in the warm waters of Rowleys Bay, kayak the sandy shore, and wake to the sounds of seagulls and waves. This unique cabin is located on the shores of Lake Michigan in a wooded setting just a short drive to Sister Bay, making it the perfect home base for your weekend in Sister Bay. Truly the best of both worlds offering inland lake-like swimming, with ocean-like views of Lake Michigan.

where to stay in Sister Bay, Wisconsin - Door County A-frame

The only downfall we can see? You might find yourself wanting to just stay at the cabin instead of venturing out to explore all that Sister Bay has to offer. Win, win.

Note: Door County Cabin Collective does book out quicker than other vacation rentals in the area, so don’t delay in making your reservation as soon as possible. Check out all the details, booking info, and more photos of this Door County A-frame here. Your dates booked? A back up option just a 15 minute drive up the cost is Porte Haven and has the additional benefit of taking Jens Jensen’s windy road to the cabin (most popular road in Wisconsin) and views of Washington Island.

Weekend activities in Sister Bay, Wisconsin

If I only had 3 days in Sister Bay, here’s how I would fit in all the best things to do in Door County in that amount of time.

Day 1:

First things first, once you’ve decided on your dates, run – don’t walk to book a reservation at the Wickman House. They open up dates 3 months in advance and it is extremely difficult to get a spot at this phenomenal restaurant. Every single person that goes here says it’s the best meal they’ve ever had, and I have to say – the cocktails make the trip worth it alone. My pick: spicy mojito – make sure to get there early and enjoy it on the outdoor patio under the twinkly lights.

best restaurant in Door County - Wickman House

Here are some backup dinner options if you cannot get into Wickman House: Chop and Lure. Owned by the same amazing family, you cannot go wrong with either one. Chop if you’re looking for a steakhouse and Lure if you’re in the mood for seafood.

Now that we’ve got dinner on day 1 set, let’s talk about the drive to the cabin up Hwy 42, which is an absolutely stunning route going through all the towns of Egg Harbor, Fish Creek, Ephraim, and to your destination: Sister bay.

My recommendation is to hit some of the hot spots on your way there so you don’t have as much driving to do once your weekend starts and you can hunker down at the cabin and relax for a little while or stay in Sister Bay to make sure you see all that she has to offer.

Stop 1:

You’ll know you’re entering Fish Creek along Hwy 42 as you wind down into the village from the bluff. “With its back to a rock and its face to the sea”, Fish Creek may just be tied with Sister Bay for favorite village in Door County by repeat visitors. Just a warning, you’re going to take a walk down Main Street and know you need to plan a trip back to see more of Fish Creek. For now, take in all the cute historic buildings and stop at one of the shops – our favorite: Sister Golden.

Stop 2:

Anderson's dock in Door County WIContinue your way up the coast another 10-15 minutes and your next stop is in Ephraim at Wilson’s, a 1950’s old-fashioned ice cream parlor to grab a treat and take in one of my all-time favorite views in Door County. Make it magical and schedule this for just before sunset. Walk or drive 2 minutes up the road to Anderson Dock, an iconic photo spot in Door County to set the stage for your weekend. Bonus tip: bring some paints, you’re allowed to put your stamp on the place and graffiti the building. You’ll see a sign out front explaining the history and reason for the graffiti: boaters have signed their boat’s names and the year they docked in Ephraim for years. Leave your family name and year of visit!

Stop 3:

If you need groceries for the weekend, we recommend stopping at Piggly Wiggly in Sister Bay. You’ll find many local treats and products to enjoy like Kickash Granola (seriously the best EVER), toffee, cocktail cherries, wine, coffee – load up on all your favorites in one spot!

Now it’s time to settle in at the cabin and get ready for your dinner reservation! Post dinner we recommend a fire in the fireplace with a glass of wine you picked up on the way into town and a family game night to cap off the perfect first day of vacation.

Day 2:

Kick off your day with famous Swedish pancakes and visit the goats on the roof at Al Johnson’s. It’s open from 7am – 3pm and the earlier you get there, the less of a wait. If there happens to be a wait, check out the Butik which is a shop right in the restaurant, or take a walk along the boardwalk and check out the sailboats in the marina. It’s worth the wait and our recommendation on what to order is the Swedish Pancake special. It really is worth the hype.

Pick an adventure:

Peninsula State Park and check out Eagle Bluff Lighthouse, feed the chickadees or rent mountain bikes.

Sail Door County – our favorite is a sunset cruise, there’s nothing like checkint out Door County from the water.

Bayshore Outdoors – rent kayaks and take a tour or if it’s winter, rent cross country skis, snowshoes and bikes.

Pirates Cove Adventure Golf – always a quintessential family vacay activity!

Silver Strike Charter Fishing – yearround services and guided tours – fish for King Salmon, Walleye, Bass, Whitefish, and Trout!

Dog Park – bringing your pup with you? Perfect, there’s a dog park on Woodcrest Rd just east of Hwy 42.

When you’re ready for lunch or dinner, head to Wild Tomato – we promise it’s going to be the best wood-fired pizza you’ve ever had. We recommend The Green & Gold – pizza topped with Renards Cheese curds? Yes please.

Late-night plans:

No kids evening option: Live music at Husby’s or the Stabbur (courtyard bar next to Al Johnsons!) – we always check out both and see which music we prefer!
Kids evening option: Bowling at Sister Bay Bowl and if you’re looking for dinner, it’s highly recommended here. Not your average bowling alley food, that’s for sure!

Day 3:

Checkout at the cabin is 10am which is ok because you’ll want to get out and sightsee your final day in Door County. I recommend you take the opposite drive down the peninsula for the scenic road of Hwy 57 on your way out to get a taste of the “quiet side” of Door County.

It’s worth it for the beautiful surroundings alone, but we’ve got some fun stops in store for you along the way as well.

scenic drives in Door County hwy 57

Stop 1:

You’ll drive through another one of our favorite villages: Bailey’s Harbor. Take note of a few stops for your next trip like Chives, Door County Brewing, and a photo stop you might want to check out is the famous Boynton Chapel.

Stop 2:

Whitefish Dunes State Park and Cave Point – miles of dunes and hiking along the water, it’s my favorite hike in the entire county. Hike up the tower to Old Baldy and you’ll be able to see amazing views for miles. Cave Point, indisputably the most photographed spot in all of Door County is technically a separate park, but it’s one minute up the road from Whitefish Dunes. Take a hike, then get your photo and check out what all the hype is about!

Stop 3:

Door County Candy in Sturgeon Bay on the way out of town. You will be parents of the year, I promise you. An old fashioned confection store, you’ll take a trip down memory lane and find all the flavors of your childhood plus homemade candy that will keep you happy the entire way home.

There you have it! A lot of our favorites crammed into a weekend in Sister Bay. What did we miss? Any other itinerary requests?

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