Wisconsin was one of the few states I had yet to visit on my quest to see all 50 before I turn 50, so we chose it as the destination for our summer vacation. After getting recommendations from several Midwesterners, we settled on Door County – a charming peninsula that seemed to offer the perfect blend of relaxation, adventure, and culture. Nestled between Green Bay and Lake Michigan, its shoreline is dotted with small towns, scenic parks, and endless opportunities for water activities. Door County felt like a grown-up version of summer camp. With no Starbucks or chain stores in sight, it maintains a truly local, authentic vibe. It’s the kind of place that feels like a real summer escape and a welcome opportunity to unplug. The itinerary below reflects our July 2025 trip with our 8- and 11-year-olds in tow.

Practical Takeaways

• We flew into Chicago, spending two days there. We then drove up to Door County with an overnight stay in Milwaukee. In total, this is roughly a four and half hour drive, but a scenic one. We also made a quick thirty-minute stop to see Titletown in Green Bay.
• While we stayed in a motel in Door County, this is the type of destination where you would ideally want to rent a cabin for a week to fully unwind. 
• Back home on the East Coast, the weather was a sweltering 100 degrees, with humidity so thick it felt like you were breathing underwater. In contrast, Door County offered a welcome relief with July. Temperatures hovered around a comfortable 85 degrees, with plenty of sunshine and almost no humidity. In other words, it was the perfect summer escape.

Accommodations

Fresh Coast Motel
This recently renovated motel offers clean, bright rooms in a perfect location. It’s right across the street from Fish Creek Public Beach and a short walk to town. It’s also worth mentioning that it had the most comfortable beds I can recall in a motel. I highly recommend staying here if you’re not renting a house in Door County.

Door County Activities

Walk Around the Towns
Each of the waterfront towns in Door County has a unique, quaint feel. We stayed in Fish Creek, which had adorable shops to explore. There are plenty of souvenir shops, boutiques, and galleries. Sister Bay was equally fun to walk around, with the added distinction of Al Johnson’s Skal, attached to the famous Swedish restaurant. This one-of-a-kind retail experience offers a wide selection of Scandinavian housewares, clothing, and accessories.

The Cherry Hut
Our first stop in Door County was The Cherry Hut. We enjoyed a delicious lunch, sampled beer from Bridge Up Brewery, and shopped for cherry preserves, cherry coffee, and cherry salsa. It was the perfect place to relax after a long drive and embrace the Door County vibe. Don’t pass up the pork rib tips with cherry sauce!

Peninsula State Park
This is the gem of Door County. It’s an outdoor escape with unparalleled opportunities to immerse yourself in nature. Watching the sunset over the bay at Peninsula State Park is unforgettable. We did this on our first night, without knowing much about the park, and simply pulled over at a random spot along the bay. The kids and my husband skipped stones while wading in the water. I relaxed while taking in the spectacular view. It was a perfect evening.

The best way to explore the park is by bike. We rented bikes from Edge of the Park, located right at the park entrance and near the bike trail. They directed us to the 9.6-mile Sunset Bike Trail. We completed 6 miles with our kids in tow. While relatively flat, there are a few hills that tested our 8- and 11-year-olds’ abilities. The highlight of the ride was the stop at Nicolet Beach. We parked our bikes and waded in the water, wishing we had brought bathing suits and towels! We all felt quite accomplished (and tired) afterward.

With more time, we would have loved to see a show at Peninsula Players Theatre, an outdoor performance space under the stars.

Door County Adventure Rafting
If you’re planning a trip to Door County, stop reading and sign up for this tour right now. This zodiac boat trip (essentially a motorized raft) was one of the most thrilling and fun activities we’ve ever done on a vacation. My daughter had the biggest smile I’ve ever seen for 90 minutes straight. My son was hesitant at first and clung to the back of the raft. Eventually made his way to the front and couldn’t stop laughing.

This tour is not for the faint of heart. The raft goes at unexpectedly high speeds with music blasting to match the adrenaline. In addition to the excitement, you’ll learn about the area and get up close to shipwrecks. Truly unforgettable.

Skyway Drive-In Theater
Step back in time to the 1950s, grab some popcorn from the concession stand, and enjoy a movie from the comfort of your car. We watched How to Train Your Dragon and had such a fun time. If you’re watching from the back of an SUV, as we did, I highly recommend bringing pillows and blankets to make it cozy. Many people also brought lawn chairs to set up in front of their vehicles (clearly more experienced than we were).

Dining

Kettle Black Fish Boil
Door County is known for two culinary staples: cherries and fish boils. This boil is similar to a crawfish boil, with corn, potatoes, salt, and fish (whitefish, in this case) cooked all together. What sets it apart is the cooking method. The pot is set ablaze with a massive fire, instantly cooking the ingredients in just minutes. It’s a dramatic spectacle that results in a delicious, flavorful meal. This is followed, of course, by cherry pie.

Several restaurants offer fish boils on a regular schedule. Kettle Black worked best for our timing, and they accept online reservations. It’s a Door County experience not to be missed.

Wilson’s Restaurant & Ice Cream Parlor
One of the oldest and most iconic lunch spots in Door County, Wilson’s offers standard diner fare, but it’s best known for its ice cream and outrageously large frozen creations. We shared a banana split between the four of us and enjoyed homemade Italian sodas – a perfect treat on a warm summer day.

Wild Tomato Wood-Fired Pizza
Many people recommended we try Wild Tomato, and for good reason – the pizza is fantastic. I recommend the Hot Honey. There are locations in both Fish Creek and Sister Bay. We heard the Sister Bay location was nicer, but we were too tired to go far from our motel at the end of the day. We picked up pizza from the Fish Creek location and ate at the picnic tables by Fish Creek Beach, an excellent way to wind down after a full day.

Helpful Hints

• There were so many places we didn’t get to visit—partly due to time, but also because Door County is the kind of place where you want to slow down and savor the moment. A few spots still on my list include Ridges Sanctuary, OneEighty Petals, Peach Barn Farmhouse & Brewery, and PC Junction.
• And yes, it feels sacrilege to visit Door County without going to Not Licked Yet, but we may have overdone it at Wilson’s. Next time!
• I listened to the Door County episode of the Amateur Traveler Podcast in advance, which gave me lots of ideas for the trip, including the recommendation for Door County Adventure Rafting.