A Sassy Guide to Door County, WI

My friend Regan grew up in Door County, Wisconsin so when she said we should go visit for the weekend this fall I jumped at the chance to get out of the city. Below is our itinerary of eating, drinking, and leaf peeping around Door County.

Also, a few people asked about our Airbnb…it was my friend’s parent’s house so not for rent unfortunately haha, but there are plenty equally as adorable places online that I saw.


We got to Door County around 1pm and went straight to Highway 42 to leaf peep. At the tip of the peninsula just pass Gills Rock is this windy stretch of road that is amazing for photographs. And just about everyone and their mother gets out of the car to take pictures. If you have time, at the end of this road is the ferry to Washington Island. We didn’t go out there since we had other plans, but I’ve heard it’s gorgeous in the winter!

We were still in the mood for leaf peeping, so we drove over to Ellison Bay Bluff to the scenic overlook. We got there right in time for sunset and it was just epic gorgeousness with all the fall colors looking over the water. You can also hike around here if you are looking for more to do FYI.

For dinner, we drove to Ephraim to go to dinner at Trixie’s. To say this dinner was just next level amazing is not doing it justice. The service, ambiance, and food was above amazing and for sure one of the best meals I have had in 2020. Must orders: the sparkling Lambrusco, cacio e pepe (always on the menu!), and the pork chop. The pork chop 100% tasted like what fall is.

Before dinner, we had to wait a little bit and they sent us over to the Isley Coffee’s backyard for ciders & beers. It was so cute back there with little fires and Adirondack chairs. Perfect option if the wine bar across from Trixie’s is packed like it was when we were there.


The girls all went for a walk in the morning while I slept (sorry not sorry I was exhausted), but there is plenty of hiking and walking trails around the area. After their walk, they brought back burritos from Good Eggs. They usually have a line out the door, but during COVID you can actually order online and pick up! Definitely recommend that!

We got ready and headed over to Bailey’s Harbor to grab coffee at Bearded Heart Coffee (100% get the Beautiful Burnt Goat which is goat milk and caramel!) and then go next door to Jackalope Trading Co. next door to go shopping. Bailey’s Harbor is a smaller town so not much else to do except a nearby brewery and a few food trucks. It would be perfect to come coffee, shop and then lunch and move on like we did!

Next we headed to Fish Creek for more shopping – Sister Golden, Alpaca to Apparel, Blue Ivy – and then a nice little walk along the water before heading to Stone’s Throw Winery for some afternoon wine and charcuterie. Stone’s Throw is doing winery tours, but we just got a picnic table behind the wine bar and hung out and drank a few bottles before going to Hatch Distilling for a pre-dinner drink and then home to make homemade pizzas and have a dance party.


We got up early to head home stopping at Kick Coffee in Sturgeon Bay on our way out of town. It was a quick trip with just a few stops along the way, but it was exactly what we needed in a little escape from Chicago.