Ultimate Spring Break Road Trip from Chicago to Door County

Chicago to Door County Road Trip

A road trip from Chicago to Door County is your best way to spend spring break or a week of summer. This spring break road trip from Chicago to Door County will take you through some of the most beautiful parts of the Midwest, cultural experiences, local cafes, quaint towns, delightful culinary adventures and it will end with a few days of relaxation on the shores of Lake Michigan. 

How Long Does it Take to Drive from Chicago to Door County, Wisconsin

The drive from Chicago to Door County is approximately 230 to 250 miles and takes about d4 to 5.5 hours, depending on traffic. However, I encourage you to take the coastal route on US-41 that leads into the Door County Coastal Byway. It is about 280 miles. The coastal route promises a more relaxed and visually appealing alternative to the faster-paced Interstate-94. The coastal route does add an hour or two depending on how many stops you take.

Spring Break Road Trip from Chicago to Door County via I-94
Spring Break Road Trip from Chicago to Door County via I-41 and Door County Coastal Byway

Planning a Spring Break Road Trip from Chicago

The best time to visit Door County, Wisconsin, largely depends on the type of experience you’re seeking and your personal preferences. Door County offers distinct charms throughout the year, each season bringing its own unique attractions. Here’s a breakdown of the best times to visit based on different factors:

1. Summer (June to August)

  • Weather: Summer is the peak tourist season in Door County. The weather is warm, with temperatures ranging from the mid-60s to mid-80s Fahrenheit (18-30°C).Can be humid. 
  • Activities: This is the ideal time for outdoor activities, beach outings, water sports, and exploring the vibrant towns. Most attractions, shops, and restaurants are fully operational during these months.
  • Events: Numerous festivals and events take place, offering a lively atmosphere.

 2. Fall (September to October) 

  • Weather:  Fall brings cooler temperatures, with highs in the 50s and 60s Fahrenheit (10-20°C). Nights can be crisp.
  • Foliage:  Door County is renowned for its stunning fall foliage. The vibrant colors of the changing leaves make for breathtaking scenery, especially in Peninsula State Park.
  • Harvest Season: Visit local orchards and farmers’ markets for fresh produce and enjoy the quieter atmosphere after the summer crowds disappears

 3.Spring (April to May): my personal favorite time 

  • Weather: Spring brings milder temperatures, ranging from the 40s to 60s Fahrenheit (4-20°C). It’s a time of renewal, with flowers blooming and nature coming back to life
  • Avoiding Crowds: Spring allows you to experience Door County with fewer tourists. It’s a great time for quiet exploration and enjoying the natural beauty.
  • Cherry Blossoms: If visiting in late spring, you may catch the cherry blossoms in full bloom.

4. Winter (November to March)

  • Weather: Winter is the quietest season in Door County, with temperatures often dropping below freezing. Snowfall can be significant.
  • Winter Activities: If you enjoy winter sports like cross-country skiing or snowmobiling, Door County has trails and parks that cater to these activities.
  • Cozy Atmosphere: Winter is perfect for a cozy getaway. Many accommodations offer winter packages, and the holiday season brings festive events.

– Personal Preferences:  Consider what activities you enjoy. If you love outdoor adventures, summer might be your preferred time, while those seeking a more relaxed atmosphere might enjoy the tranquility of fall or spring. 

What to Expect on a Road Trip from Chicago 

During most times of the year, there’s nothing more certain you can count on around Chicago. Traffic and tolls and sometimes road construction. But most of those are inevitable and we make the most of it. One of the three can be avoided if you leave your home early. We left for our spring break road trip from Chicago around 5 am and there was not any traffic. Leave early and your commute wont look like this and you won’t be another statistic that’s stuck in traffic for 155 hours per year. 

Chicago Traffic on I-94

And for the oh so lovely tolls, if your home state uses the EZ Pass system, bring your transponder, it will work on Illinois tollways. If you do not have a transponder, bring cash and change. 

Car Rental Options for a Road trip from Chicago to Door County

If you are flying into O’Hare Airport, you will need a rental car. Our preferred rental car is Hertz. They always have the best rates, are reliable and their customer service is amazing. 

Alternatively, compare rates with other rental car companies here

Another great, affordable and convenient option would be to rent a campervan or RV for your road trip. Renting a campervan or RV could save you money, as you won’t have to spend money on lodging. It will also give you tons of flexibility on the road. Imagine sleeping right next to shore in the comfort of the back of your van and waking up to fresh spring air immediately. 

Campervan Rental

Make the dream come true by renting a Camper Van or RV on Outdoorsy. Make sure your insurance covers rentals and don’t rely on their insurance. Take your own photos before taking possession of the rig, don’t break anything, and you’ll be just fine. You will get your deposit back once the owner confirms there was no damage during the rental period.

Spring Break Road Trip from Chicago to Door County Logistics

Miles280
Drive Time5.5 hours
Days4-5 (can be shortened to fit your needs)
Beautiful Highways DrivenI-41 and Door County Coastal Byway( with views of Lake Michigan throughout) ,Lakeshore Scenic Byway, Kettle Moraine Scenic Drive
Major CitiesChicago, Milwaukee, Door County
Coastal Towns10+
Islands 3
CostPriceless
Spring Break Road Trip from Chicago to Door County

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Day 1: Chicago to Milwaukee via The Lakeshore Scenic Byway

Starting PointChicago,Illinois
DestinationMilwaukee,Wisconsin
Distance135 miles
Drive time(with stops)3.5 hours
Day 1: Spring Break Road Trip from Chicago

Start your road trip from Chicago to Door County early. Before you leave Chicago, grab yourself some coffee and a breakfast sandwich at Black Fodder Coffee. They open at 6 am. It was the only coffee shop open that early. After you’ve got your coffee go north on I-41 and start your spring break road trip from Chicago.

By opting for US-41, you not only avoid the typical Interstate-94 monotony but also open yourself up to a world of hidden gems and local treasures. From charming cafes to breathtaking beaches, this spring break road trip from Chicago promises memories that will last a lifetime.

Places to Stop between Chicago and Milwaukee

Stop 1: Evanston

Only after you’ve had a couple sips of your coffee, begin your journey driving 30 minutes north of Chicago towards Evanston. Only 15 miles north of Chicago , the town of Evanston carries quite the charm. Stop in downtown Evanston for a lighthouse viewing , or head to the Evanston farmers market where a sizable amount of vendors are selling great products. 

Grosse Point Lighthouse

Leaving Evanston, hop onto US-41, aka Lakeshore Drive then Sheridan Drive, a scenic highway that hugs the coast of the western shore of Lake Michigan. The  “Lake Michigan Circle Tour” signs will help you to follow Sheridan Road as it can get a bit confusing with all the twists and turns….sights along the way sometimes charge a fee, like the beaches, BUT, if you get there early enough, say before 7 or 8, maybe 9 am, then you can get on for FREE…. also, some places charge a parking fee, but are FREE to walk in…..

I recommend you get a Wisconsin State Park Pass for $38. Each entrance fee will be at least $10, so a $38 pass makes total sense.

Stop 2: Gilson Beach and Glencoe Beach 

Drive about 15 minutes north to Gillson Beach  or Glencoe Beach for a relaxing morning by Lake Michigan. 

Both Gilson Beach and Glencoe Beach are pretty.  Glencoe Beach has a playground for kids, bathroom and changing rooms. During the summer there is a $10 entrance fee. 

Gillson Beach on a sunny day – via Flickr Jonathon Lurie

Just some notes on Gillson Beach- Nearby parking is reserved for permit-holders, but there is unrestricted parking along the park periphery and many of the side streets. It is best to get there before 11 am.

There are many  large expanses of green for picnics and play and just to soak in the views of Lake Michigan on hopefully a sunny day during your spring break road trip from Chicago.

Stop 3: Lake Geneva 

After you have visited the beaches and got in some vitamin D, start making your way to Lake Geneva, the hidden gem of the midwest. 

Between Lake Geneva and Chicago you will find TONS of antique shops, keep an eye out for little ones along the side of the road, those are the best. If you do end up taking I-94, many travelers on I-94 like their first Wisconsin stop to be the Outlet Mall in Pleasant Prairie. It’s just across the Illinois/ Wisconsin border.

Approximately 1 hour and 60 miles north on I-41, you will arrive at Lake Geneva and it’s the perfect place to grab lunch and stroll around the beautiful lakefront. 

If you have time to walk around, The Geneva Lake Shore Path is something that everyone should take a walk through at some point in their lives. Walking the path offers a  beautiful up close view of the lake and the massive mansions surrounding it.  

It is accessible via a few public access points in Lake Geneva, Fontana, Williams Bay and at Big Foot Beach State Park. 

Geneva Lake Short Path

At Lake Geneva Stop at  Big Foot Beach State Park and access the shore path from there  or you can go straight to  Riviera Beach, the main beach. There you can find room for you and your family to just sit or dip your toes for a bit. 

Riviera Beach in Lake Geneva via Lake Geneva

There are a handful of boutiques on the main drag, like Twelfth and Brown. Their clothes are reasonably priced and you can find almost any piece of clothing if you find you need something. Most items are priced under $50 (2023) .

Speaking of lunch you’ll want to stop at Upper Crust in Lake Geneva. One of the best pizza places we’ve ever been to.  

Another option may be for something more upscale may be Sopra. They offer American cuisine with a charm. 

For something on the lake try, Oakfire, it’s a pizzeria with lakefront views. 

Oakfire Pizza Restaurant in Lake Geneva

For some more coffee before you hit the road again, go to Avant Cycle Cafe

Latte at Avant Cycle Cafe in Lake Geneva

By now it is early afternoon, and you want to start making your way to Milwaukee, which will be the last stop and resting stop for day one of this spring break road trip from Chicago to Door County.

Stop 5: Milwaukee

Make your way to Milwaukee via I-43N, about 50 miles from Lake Geneva. Once in Milwaukee, start exploring! Start with Historic Third Ward.

The Historic Third Ward is located in the downtown area off the river and a true Milwaukee gem area, buzzing with excitement. It’s Milwaukee’s oldest center of commerce area in the city.

Filled with boutiques, galleries, and cafes, there is truly something for everyone.  It’s such a lively little town that gives you a hint of what historic Milwaukee could have been like. There are decently priced parking lots( $5 to $10) , there is also street parking.

I highly recommend that you check out Milwaukee Public Market , filled with an abundance of multi-ethnic cuisines. They’ve also got everything from fresh meats and famous Wisconsin cheese to unique spice vendors that your taste buds will savor. My personal favorite eatery was the  St. Paul Fish Company for their lobster boil.  In the mood for a giant Philly Cheesesteak, they’ve got that too! 

Milwaukee Public Market

If you are a reader, they’ve got an exceptional book store Downtown Books Bought & Sold with the cutest cats roaming in the store. You will walk out with a book you can put down for the rest of your road trip. Psss.. if you’re allergic to cats, don’t go. There a few  friendly cats perched among the books that follow you around just to make sure you find your perfect book. 

Milwaukee Book Store

Best Places to Stay in Milwaukee

In the evening, check into a cozy Milwaukee hotel, like The Pfister Hotel or Kimpton Journeyman Hotel.

Best Places to Eat in Milwaukee

Sanford -is very pricey and very upscale and serves American cuisine

Lake Park Bistro– for french cuisine, also very pricey

Milwaukee Public Market is great for all types of cravings and is my go to place for eating

Day 2: Milwaukee to Sheboygan via Kettle Moraine Scenic Drive 

StartingMilwaukee
DestinationSheboygan
Distance 60 miles
Driving time 1.5 hour(with stops)
Day 2 of Spring Break Road Trip from Chicago
Day 2 Spring Break Road Trip from Chicago

You may think this leg of the spring break road trip from Chicago to Doors County is a boring one, but I assure you it’s anything but. From Milwaukee, you’ll head northwest (about 40 miles) towards the city of West Bend. West Bend is the starting point of the upper third northern section of the Kettle Moraine Scenic Drive. From there, you will follow green acorn signs, to guide you along the scenic drive. 

But first, coffee. Starting in Milwaukee, you will want to grab your first coffee (of many) Colectivo Coffee on the Lakefront. It’s got such a nice lush setting for seating. Perfect to enjoy your warm or iced beverage.

Colectivo Coffee in Milwaukee

Places to stop between Milwaukee and Sheboygan

Stop 1: Lannon Sunflower Farm

If you are heading on this road trip sometime in July or August then, it is your time to see a sunflower farm! On the way to West Bend pass through Lannon Sunflower Farm to see farms of Sunflower and snap a beautiful picture. It is quite magical.

Sunflower Farm Milwaukee- Milwaukee Mag

Stop 2: The Kettle Moraine Scenic Drive

Driving along the Kettle Moraine Scenic Drive has just about everything your eyes would want to see. It is dotted with many intriguing stops and captivating sights that I will outline below . Embarking on the Kettle Moraine Scenic Drive from Milwaukee to Sheboygan unveils a journey through Wisconsin’s picturesque landscapes, dotted with intriguing stops and captivating sights. 

Snippet of Kettle Moraine Scenic Drive via google maps

Do keep in mind most of the route is on local or county roads so your speed will be limited(most roads are 35 mph).

Stop 3: Widmers Cheese Cellars

Your first stop on this drive may or may not include a stop at the 100 year old Widmer’s Cheese Cellars. Watch and learn how cheese is made right before your eyes. It was such a fun experience getting to see the process of how cheese is made. They have a small retail store to purchase cheese and they give out samples.

Widmers Cheese Cellar via Trip Advisory

Stop 4: Kettle Moraine State Forest

Further along the drive, immerse yourself in the natural beauty of the Kettle Moraine State Forest, where rolling hills, pristine lakes, and dense forests offer endless opportunities for hiking, birdwatching, and scenic overlooks. The state forest is large and covers over 50,000 acres.  They have a $5 entrance fee per car.

Stop 5: Maude Lake Recreation Area

While at the state forest, check out Mauthe Lake Recreation Area. I would say it is the perfect stop for lunch, perfect place to have a picnic. They have got plenty of picnic tables, right next to the lake. Such awe. $11 to enter. Grab some sandwiches and (more coffee) from Coffee Corner Bistro and have yourself a peaceful picnic and place to stretch your legs while gazing out at still water. If you are in the mood for some pizza, get yourself some Michaleno’s Pizzeria.

Maude Lake Recreation Area with picnic tables

Stop 6: 3 Sweets Bakery & Cafe

After you are done getting lunch, or having a picnic at Maude Lake, if you desire something sweet, get something from 3 Sweets Bakery & Cafe. It is right on the scenic drive, so you won’t have to make any detours. 

Stop 7: Parnell Tower

By now you should be satiated, so you can keep exploring the state forest. Head further north so you don’t miss the captivating views from Parnell Tower, where panoramic vistas of the surrounding countryside await. It took about 10 minutes to walk to this tower from the parking lot. It’s a wooden tower with 96 that is quite sturdy, so don’t worry about it collapsing. The view from this tower was gorgeous. 

Parnell Tower via Visit Sheboygan
Kettle Moraine Scenic Drive – lots of country greenery and slow driving to take it all in

Stop 8: Elkhart Lake

Continuing further north you will reach the last stop of the Kettle Moraine Scenic Drive, Elkhart Lake. Here you can capture the sheer beauty of Lake Michigan, with sand dunes, beautiful wooden walking paths, and we even saw a white tail deer.

Elkhart Lake

It is a perfect place to settle down for the night or a perfect place to pass through and finish the night off in Sheboygan (it’s quite the name) aka the Malibu of the Midwest. 

Where to Eat Along the Kettle Moraine Scenic Drive

Along the Kettle Moraine Scenic Drive from Milwaukee to Sheboygan, you’ll find a variety of delightful dining options that cater to every taste bud and preference. Here are some of the best places to eat along this picturesque route, most are in Kewaskum. Kewaskum, Wisconsin, may be a smaller town, but it still offers some excellent dining options that cater to various tastes and preferences.

The Cheel: Located in Thiensville, this cozy restaurant specializes in authentic Nepalese and Tibetan cuisine, offering a unique culinary experience. From savory momo dumplings to flavorful curries, The Cheel promises a delicious meal that will satisfy any food enthusiast.

3. The Columbian Inn Restaurant & Tavern: Located in the heart of downtown Kewaskum, The Columbian Inn offers a cozy atmosphere and a menu featuring classic American dishes. From hearty burgers to comforting pasta dishes, there’s something for everyone here. Don’t miss their Friday fish fry, a local favorite.

Michaleno’s Pizzeria: Located in Kewaskum, it’s the perfect place to stop and enjoy some pizza. It is right on the scenic drive. 

Timmer’s Resort: Just a short drive from Kewaskum, Timmer’s Resort is situated on the scenic shores of Big Cedar Lake. This lakeside restaurant offers upscale dining in a picturesque setting. Indulge in fresh seafood, steaks, and other gourmet dishes while taking in breathtaking views of the lake.

Field to Fork Cafe : As you approach Sheboygan, make a stop at Field to Fork Cafe for a farm-to-table dining experience. This cozy eatery sources ingredients locally, crafting seasonal menus that highlight the best of Wisconsin’s bounty. Indulge in dishes made with fresh, sustainable ingredients that celebrate the region’s agricultural heritage.

Along the Kettle Moraine Scenic Drive, there are several lakefront dining options where you can enjoy delicious food with stunning views of the water. Here are some recommendations:

Anodyne Coffee Roasting Co. – Milwaukee, WI : Anodyne Coffee’s Walker’s Point location offers a unique lakefront dining experience on the shores of Lake Michigan. Enjoy locally roasted coffee, delicious pastries, and light bites while taking in the serene views of the lake from their outdoor patio.The interior is sprawling. 

Anodyne Coffee Roasting Cage

The Osthoff Resort – Elkhart Lake, WI

For an upscale lakefront dining experience, consider dining at The Osthoff Resort’s Lakeside Dining Room. This elegant restaurant overlooks beautiful Elkhart Lake and serves gourmet cuisine made with locally sourced ingredients. Enjoy fine dining in a picturesque lakeside setting.

These lakefront dining options offer a perfect opportunity to savor delicious food while admiring the natural beauty of Wisconsin’s lakes and rivers along the Kettle Moraine Scenic Drive. Whether you’re looking for upscale dining or a casual meal with a view, these establishments are sure to enhance your scenic drive experience.

Where to Stay in Sheboygan

Check into a charming bed and breakfast like The Rochester Inn or one of the charming Airbnbs.

Day 3: Sheboygan to Green Bay via The Door County Coastal Byway

StartingSheboygan
DestinationGreen Bay
Distance60 miles
Driving Time 1.5 hours(with stops)
Spring Break Road Trip from Chicago

Start your day early… with breakfast and coffee at Field to Fork or Z Spot in Sheboygan and then start driving on  scenic routes Highway 42, which offer picturesque views of Lake Michigan and the surrounding countryside which include the best little farmers markets.  You can totally also drive inland and take I-43 to Green Bay, which would take 30 minutes less, but I am here to show you the fun route. Take the scenic country road, the detour is beautiful and worth the extra 10 miles or so. 

Also, no matter which way you take to get up there, pack a decent sweater. Depending on the wind and where you are, a breeze off the lake can be pretty chilly. It’s not unheard of to change 15° by moving couple miles inland.

Places to Stop between Sheboygan and Green Bay

Stop 1: Cleveland, WI (Approx. 20-minute drive from Sheboygan)

I love parks and outdoors, I am not sure if it has been evident. So naturally, the first stop has to be a beautiful open Hika Park with Lake Michigan in the background putting on a show. Grab your coffee and just watch the sunrise as you get ready to embark on the adventures ahead. They get bonus points because they have bathrooms!

Hika Park

Stop 2: Manitowoc, WI (Approx. 30-minute drive from Sheboygan)

Wisconsin Maritime Museum: Learn about the maritime history of the Great Lakes region at this fascinating museum. Explore interactive exhibits, tour historic vessels, and climb aboard the USS Cobia, a World War II submarine.

Manitowoc County Cherney Maribel Caves Park: Check out pretty cold caves primarily formed by glacial activity. See a massive Dolomite and you can also go inside the caves. Maribel Caves is lovely. The hike/walk isn’t challenging, and the river, the caves and the dolomite formations are really amazing. Bring a picnic lunch, or just sit in a quiet spot to take it all in.

Manitowac County Caves

Stop 3: Two Rivers, WI (Approx. 15-minute drive from Manitowoc)

When you get to Two Rivers, make sure you pronounce it like a local. It is pronounced T’Rivers.. Like it’s one word. Two Rivers is where the East Twin River and the West Twin River come together to form the Great Lakes. Don’t miss it! It is also a great place  to stop at for lunch and fresh seafood. 

Rogers Street Fishing Village: Step back in time at this living history museum, featuring historic buildings, exhibits on Great Lakes maritime heritage, and replica fishing vessels. Take a guided tour to learn about the area’s rich fishing industry. Plan to spend at least an hour. 

Point Beach State Forest: Stretch your legs and enjoy the natural beauty of Point Beach State Forest. Here you’ll get six miles of sandy beach. Hike along scenic trails, relax on the sandy shores of Lake Michigan, or have a picnic amidst the peaceful surroundings. You need a state park sticker to access the park. The walk from parking to the beach is not far. There is a lighthouse but it is not publicly accessible. There are many picnic tables and areas for seating, so it would be a great place to grab lunch and have a picnic. $8 to enter. 

Neshotah Park: If you still need more doses of water and beach and soft sand then go to Neshotah Park. It’s a beautiful beach nestled in a beautiful park. It is another resting stop and place to get some soft feet because let me tell you, their sand is super soft.. It does not have those rocks that you normally would get at most beaches.

Neshotah Park

Two Creek Park:  For more beautiful views of Lake Michigan, visit Two Creeks Park. Another place to dip your toes and view unobstructed views of Lake Michigan.

Two Creeks Park – perfect spot for picnicking and listening to waves of Lake Michigan
Two Creeks Park

While at Two Rivers, stop and have some lunch at one of these delicious eateries.

Fatzos: – seriously, they have the best sandwiches in town. Definitely try them out. They have hearty portions at very reasonable prices. My husband, who is 200 pounds and 6 feet tall, barely finished his sandwich! 

Rupp’s on Washington – This family-owned restaurant prides itself on using locally sourced ingredients whenever possible. Enjoy classic American fare with a focus on quality and flavor, including burgers, sandwiches, and seafood dishes.

Water’s Edge Restaurant– for lakefront dining and American cuisine try this restaurant. 

Waters Edge Restaurant

Red Bank CoffeehouseGreat coffeehouse with even greater coffee beans. Try the chai latte, you wont regret it. 

Stop 4: Mishicot, WI (Approx. 10-minute drive North from Two Rivers)

The only stop you’ll be making here, is if you need to stock up on roadtrip snacks and groceries for the remainder of your trip. Check out Lakeside Country Store for all your heart desires. They’ve got a great selection of produce and it’s great to support small businesses. Their soft serve ice cream is a hit. 

Stop 5: Kewaunee, WI (approx. 30 minutes north on HWy 42 from Two Rivers)

Continue driving along highway 42…. Most of the drive will look like this, with Lake Michigan to your left. You will pass by country homes and small farms. Sometimes they will have open stands. 

Lakeshore Road with country and lake views

You will reach Kewaunee, a sleepy and slow paced town. It doesn’t really have a strong identity because it’s a mix bag of country town, beach town, boating/fishing town, tourist stop on the way to Door County. All that being said, it’s quaint, beautiful, nostalgic, and just a great little town to pass through. 

If you like the charm of older homes, Kewaunee has some gorgeous Victorian homes listed once in a while. Maybe something will spark your interest. Here are some things to do while in Kewaunee ( say that 3 times fast) 

Kewaunee Pierhead Lighthouse visit the lighthouse which has guided ships along Lake Michigan since 1931. Take a leisurely stroll along the pier for stunning views of the lighthouse and the lake. There are no handrails or fences to keep you in, so proceed with caution. If you are a fan of lighthouses, I think you will like this one. It’s open and its free! 

Pierhead Lighthouse

Bruemmer Park Zoo: Pay a visit to Bruemmer Park Zoo, a small yet charming zoo featuring native Wisconsin wildlife and exotic species. Take a leisurely stroll through the zoo’s wooded trails and enjoy educational exhibits and animal encounters.

Lafond’s Fish Marketfor the most appetizing smoked fish you will ever taste according to the locals! 

Stop 5: Greenbay, Wisconsin (Approx. 40 minutes West on highway 29) 

Krohns Cheese Store – before you get to Green Bay, stop at the Krohns Cheese Store off highway 29 for the freshest cheese curds in Wisconsin, possibly in the nation. They’ve also got the best take and bake pizza in Northeast Wisconsin. 

Lambeau Field: No trip to Green Bay is complete without a visit to Lambeau Field, home of the Green Bay Packers. Take a stadium tour to explore behind the scenes, visit the Packers Hall of Fame, and snap a photo at the iconic Lambeau Leap statue. Prices start at $18. 

Bay Beach Amusement Park: Enjoy classic amusement park rides, including a wooden roller coaster, bumper cars, and a Ferris wheel, at this family-friendly attraction. Admission to the park is free, and ride tickets are affordable, making it a perfect destination for families. 

Stroll Downtown Green Bay-  Downtown Green Bay has a really nice historic district called the Broadway district with shops and restaurants ranging from casual to higher end. Downtown De Pere is cute to walk through, too, and has a great chocolate shop called Seroogy’s. Parking downtown is always free after 6 p.m. M-F, weekends, and holidays.

Best Places to Eat in Green Bay

Plae Bistro: Located in an historic building downtown, Plae Bistro offers contemporary American cuisine with a twist. Enjoy dishes like duck confit mac and cheese, shrimp and grits, and house-made desserts in a stylish setting.

Vintage Cantina – for unique tacos  and Super delicious combos of flavors in the tacos. 

Vintage Cantina

Los Banditos-  Mexican restaurant in Green Bay that serves up delicious food made from fresh ingredients. They have a wide variety of Mexican dishes to choose from, such as chicken fajitas, steak tacos, smothered burritos and others. If you’re looking for 

the best Mexican food in town, then Los Banditos is the place to go

Jakes– for a good ole pizza. They’re pizza was perfectly made and full of flavor.  

Jakes Pizza

Best Places to Stay in Green Bay 

Hotel Northland – stay in a historic hotel built in 1924, it’s quite lofty and spacious for your one night stay in Greenbay

Cozy Airbnbs in Green Bay under $100 a night 

Best Hotels in Green Bay under $100 per night 

Day 4: Green Bay to Sturgeon Bay via The Door County Coastal Byway

Starting Green Bay
DestinationSturgeon Bay
Distance47 miles
Driving Time 1 hour
Day 4- Spring Break Road Trip from Chicago

For this park of the trip I encourage you to get a state parks pass for $38 to get admission to all Wisconsin State Parks, as there will be many of them that you’d want to check out. 

Start your day with breakfast at Grapevine Café or Glas Coffeehouse in Green Bay. Then head northeast to Sturgeon Bay on highway-57,  opting for less-traveled rural roads for countryside views.

Stops between Green Bay and Sturgeon Bay

Stop 1: New Franken,WI (Approx. 20 min north from Green Bay) 

1.Brown County WI Bay Shore Park– this is a great place to stop if you need to. Although the drive to Sturgeon Bay is quite short. We parked up top just past the playground and hiked down to the beach. Beautiful trail along the cliffs. Very nice pebble beach at the end. You can drive down to the beach too but we enjoyed the mini hike. 

Stop 2: Sturgeon Bay,WI  (Approx. 40 minutes north of Green Bay) 

Sturgeon Bay Canal North Pierhead Lighthouse– stroll along the pier and see the famous red lighthouse. It is perfect for instagram photos! This lighthouse is located at the U.S. Coast Guard station. You can park your car in the dirt lot outside of the station. There are many warning signs which can make you wonder if you are even allowed to visit! Just park and stay on the walkway. The end of the pier can be very windy and may get slippery, so wear shoes with traction. The beautiful red lighthouse is worth a short visit

Bay Canal Pierhead Lighthouse

Potawatomi State Park– Smaller, but lovely state park with so much to offer. I did  have to pay $ 8 for the day.  The park has many trails,a lookout tower, and views of Lake Michigan throughout. 

Lookout Tower at Potawatomi State Park

Historic Third Ave – Go downtown and do some shopping. They have plenty of cute shops. So wandering the shops of 3rd Avenue for a few hours might be just up your alley. 

Historic Third Ave

Best Places to to Eat in Sturgeon Bay

Waterfront Mary’s Bar & Grill- Located on the waterfront, Waterfront Mary’s Bar & Grill offers stunning views of Sturgeon Bay and a menu of casual fare like burgers, sandwiches, and seafood. Sit on the outdoor patio and enjoy live music during the summer months

The Nightingale- a  popular supper club in Sturgeon Bay, Nightingale Supper Club offers a cozy ambiance and a menu of hearty dishes like steak, seafood, and chicken. Enjoy cocktails at the bar before dinner and indulge in homemade desserts.

The Mill Supper Club- Experience classic supper club dining at The Mill Supper Club, where you can enjoy steaks, seafood, and traditional Wisconsin favorites in a rustic yet elegant setting. Don’t miss the Friday fish fry or the prime rib special.

Best Places to Stay in Sturgeon Bay

Lovely Hotels in Sturgeon Bay 

Quaint bed and breakfast like Black Walnut Guest House or White Lace Inn

Beautiful Airbnbs in Sturgeon Bay 

Day 5: Sturgeon Bay to Door County via The Door County Coastal Byway

Starting Sturgeon Bay
DestinationDoor County
DistanceVaries
Time Varies
Day 5 Spring Break Road Trip from Chicago

On day 5 of this spring break road trip from Chicago to Door County, you will drive on one of the best scenic drives in Wisconsin, The Door County Coastal Byway inspired by Jens Jensen, a Danish architect.  

Embark on this road trip from Sturgeon Bay to Door County, and you’ll discover the natural beauty, culinary delights, and unforgettable experiences that make this region of Wisconsin so special. 

Although Door County won’t have as many doors as you think, it is stunning. People call it the Cape Cod of the Midwest. 

So, capture memories with stunning photos, indulge in delicious treats from creameries, and savor every moment of your coastal adventure.

The Door County Coastal Byway, also known as Highway 42 and Highway 57, offers stunning views of Lake Michigan and the waters of Green Bay as it winds its way through the scenic Door Peninsula. Here are some of the top things to do and see along the Door County Coastal Byway

Places to stop between Sturgeon Bay and Door County

Stop 1:  Sunrise at Canal Park

Start your day with a picturesque sunrise at Canal Park in Sturgeon Bay. Capture stunning views of the canal, lighthouses, and passing boats as the day begins. We got up super early, but it was worth the effort and worth the beautiful sunrise we captured 

Sunrise at Canal Park via Trip Advisor

Stop 2: Scenic Drive along Highway 57

Head north on Highway 57, the main coastal road in Door County. Enjoy the scenic drive with views of the sparkling waters of Lake Michigan and so many lookout points to just stop the car and soak in the view.  Allow 20-30 minutes to enjoy the scenic drive from Sturgeon Bay. 

Photo Opportunities: Keep an eye out for roadside pull-offs, scenic overlooks, and charming landmarks throughout Door County for photo opportunities. Don’t hesitate to explore off the beaten path for hidden gems.

Stop 3: Jacksonport, WI (20 minutes north of Sturgeon Bay) 

Cave Point County Park -Just 20 minutes north of Sturgeon bay is one of my favorite parts of Sturgeon Bay. This place is seriously quite the gem of Wisconsin. Marvel at the rugged limestone cliffs, sea caves, and crystal-clear waters of Lake Michigan. 

Be sure to capture stunning photos of the dramatic coastline. There is a free admission, three parking lots with free parking, restrooms and park benches. What more could you want? There were several brave cliff-jumpers when we went last time. 

Cave Point County Park somehere in Wisconsin or somewhere in the Bahamas..
Cave Point County Park

Stop 4: Egg Harbor,WI (30 minutes West of Jacksonport) 

Explore the picturesque village of Egg Harbor. Stroll along the waterfront, browse boutique shops, and admire the harbor views. Stop for a photo op at the Egg Harbor Marina or the Egg Harbor Public Beach. Spend about an hour strolling Main street shops.  Browse boutique shops and art galleries in downtown Egg Harbor. Discover unique gifts, handmade crafts, and locally made souvenirs, including pottery, jewelry, and artwork by local artists. 

Stop 5: Fish Creek (15 minutes North of Egg Harbor)

Take a scenic drive or hike to Sven’s Bluff Lookout within Peninsula State Park located in Fish Creek.  The lookout offers breathtaking panoramic views of Green Bay and the surrounding countryside, making it a perfect spot for photography and enjoying the natural beauty of Door County. Its also the best known spot for watching the sunset. 

Svens Bluff Lookout via door county coastal byway

Eagle Tower, a 100-stair, 75-foot wooden look-out tower built on the highest point of the peninsula. The 360 degree view is lovely with a great view of Lake Michigan to the north (with Horseshoe Island), the quaint town of Ephraim to the east, the remainder of the park to the south, and Nicolette Beach and park to the west.  

Fish Creek Area, with many opportunities for fun and adventure outdoors

There is plenty to do and see in Fish Creek, much of it is outdoor viewings. You can even consider staying the night and seeing the rest of Door County the next day. 

Stop 5: Sister Bay,WI ( 15 minutes North of Fish Creek)

Al Johnson’s Swedish Restaurant & Butik

Before leaving Sister Bay, make a quick stop at Al Johnson’s to see the iconic goats grazing on the grass-covered roof. Snap a photo of this unique sight before continuing your journey. Consider stopping here for their special lunch. They’ve got yummy potato pancakes 

Al Johnson Swedish Restaurant via Destination Door County

Door County Creamery

Make a stop at Door County Creamery in Sister Bay. Indulge in artisanal cheeses, creamy gelato, and freshly made sandwiches. Don’t forget to snap a photo of the charming red barn and scenic surroundings 

Ellison Bay Bluff State Natural Area 

This is a must-stop even if you don’t want to hike. The scenic overlook is gorgeous and not to be missed. There’s a platform to walk out on that overlooks the bluff. There’s benches to sit and just enjoy the water view as well. Steps down to the overlook and you’re greeted with rugged coast below, clear water washing ashore, seagulls gliding the skies. Sit and enjoy the views.

Ellison Bay Bluff Natural Area

Stop 6: Liberty Grove, WI ( (20 min north of Sister Bay) 

Gills Rock

Explore the charming village of Gills Rock, the last town  located at the northern tip of the Door Peninsula.

Gills Rock Winding Road

Take a drive on the most photographed road in Door County, filled with curves. It was designed so one has to slow-down and take-in the surroundings. If one is the driver, however, the curves force one to pay even more attention to the road, versus the scenery. The curvy road is less than one mile. It is kind of fun to traverse a “postcard” road. At the end of the road, you’ll arrive at Northport Pier where the ferry leaves for Washington Island or plum island

Gills Rock, windy road in Door County via door county

Door County Windy Road:  bring a vomit bucket, gum or any anti nausea medication for someone that might get carsick, also let them take the front seat. The curvy part of the road is only one mile long. 

Take a ferry to Plum Island or Washington Island. It is quite the adventure and would highly recommend it. It is an all day to half day adventure so plan wisely. Park your vehicle or drive it aboard the ferry (for a $25 fee) and get ready for a ride past Plum Island and onward to Washington Island. The crew is very efficient and knowledgeable getting everyone and all the vehicles loaded and unloaded quickly.

If you make the trip to Washington Island take the passenger ferry to Rock Island State Park and you will absolutely not be disappointed. It has incredible views of the stars. The darkness is truly wonderful up there. Our family friends camp in Rock Island every year and star gazing is one of their many highlights of staying there.

Washington Island ferry – via Travel Wisconsin
Stargazing at Rock Island State Park, Washington Island on the bottom right

For some seclusion in Door County, and to get away from the tourists go to Isle View Park on the northern tip of Door County.   A picnic table and park grill are available to sit and enjoy the view. A short walk down the bluff opens up to a long strip of beach that offers amazing views of Washington Island and Lake Michigan. 

Isle View Park

Stop 7: Ellison Bay , WI( 20 minutes Lincoln Bay) 

Newport State Park

Head to Newport State Park for a breathtaking sunset experience. Find a secluded spot along the beach or shoreline to watch the sun dip below the horizon, casting a golden glow over Lake Michigan.

Or take a hike! The Europe Bay Trail and the Hotz Trail are popular options, offering scenic views of Lake Michigan, dense forests, and rolling sand dunes.

Consider camping overnight at Newport State Park to fully immerse yourself in the wilderness experience. The park offers primitive campsites for backpackers and kayak campers, allowing you to sleep under the stars and awaken to the sounds of nature. Here you can also find magnificent skies for stargazing

Experience the park’s natural beauty at dusk with a sunset hike along the trails or a twilight paddle on Europe Lake, where you can witness the changing colors of the sky reflected in the calm waters.

Stargazing at Newport State Park via Trip Advisor user sj5777 

Best Places to Eat in Door County 

  • Door Artisan Cheese(Egg Harbor)-  If you appreciate fine cheeses,  plan on a stop there. Location in Egg Harbor
  • Renards( Sturgeon Bay)- for great everyday cheese, stop on your way back up or down to Sturgeon Bay.  They’ve got the best cheese curds. 
  •  Bea’s Ho-made(Gills Rock) – for awesome pies. My favorite is cherry pie and 4 Berry 
  • Wilson’s in Ephraim (family favorite) is great for ice cream. Also for ice cream and custard you can try Not Licked Yet (Fish Creek)
  • Door County Bakery– for the best Corsica Bread ever…. If you’ve never had corsica bread, it is a must try 
  • White Gull Inn ( Fish Creek) – inn that is open to the public that serves yummy breakfast. Check out the cherry stuffed french toast 
  • Wild Tomato (Fish Creek and Sister Bay)- best pizza 
  • Al Johnson’s (Sister Bay) – Touristy place to eat and they have goats on the roof….
  • Charlies Smokehouse (Gills Rock) for some smoked whitefish to go
  • Casey’s BBQ, (Egg Harbor)- for the juiciest smoked brisket and outdoor seating and waterfront… sensational experience

Best Places to Stay in Door County 

Finding the best places to stay in Door County involves considering various factors like location, amenities, and budget. Here’s a selection of accommodations with diverse features and price ranges:

  The Ashbrooke Hotel

  •  Location: Egg Harbor
  • Features: Adult-only boutique hotel with luxurious rooms, whirlpool tubs, fireplace, and private balcony/patio options. Complimentary breakfast and evening wine and cheese reception.
  • Price Range: Starting from $150 per night.

Landmark Resort

  • Location: Egg Harbor
  • Features: Family-friendly resort offering spacious suites and condos with fully equipped kitchens, indoor and outdoor pools, whirlpools, tennis courts, and fitness center. Stunning views of Green Bay.
  • Price Range: Starting from $120 per night for a studio suite.

 The White Gull Inn

  •  Location: Fish Creek
  •  Features: Historic bed and breakfast inn offering charming rooms and cottages with modern amenities. Complimentary breakfast served in a cozy dining room. On-site restaurant famous for its fish boils.
  • Price Range: Starting from $125 per night for a standard room.

Bay Shore Inn

  • Location: Sturgeon Bay
  • Features: Waterfront resort with spacious suites and condos overlooking Sturgeon Bay. Amenities include indoor and outdoor pools, hot tub, fitness center, and complimentary paddleboats and kayaks
  • Price Range: Starting from $140 per night for a one-bedroom suitet

The Scofield House Bed and Breakfast

  •  Location: Sturgeon Bay
  •  Features: Victorian-style bed and breakfast offering elegantly decorated rooms with antique furnishings and modern comforts. Gourmet breakfast served daily. Outdoor patio and gardens.
  • Price Range: Starting from $160 per night for a standard room.

The Shoreline Resort

  • Location: Gills Rock
  • Features: Waterfront resort with modern rooms and suites overlooking the bay. Amenities include indoor and outdoor pools, hot tub, sauna, and complimentary continental breakfast. Close to ferry to Washington Island.
  •  Price Range: Starting from $160 per night for a standard room.

Eagle Harbor Inn

  • Location: Ephraim
  • Features: Boutique inn offering suites and cottages with kitchenettes and whirlpool tubs. Complimentary continental breakfast delivered to your room. Beautifully landscaped grounds with gardens and outdoor seating.
  • Price Range: Starting from $150 per night for a suite.

These accommodations offer a range of options to suit different preferences and budgets, ensuring a comfortable and memorable stay in Door County. Prices may vary depending on factors such as seasonality, room type, and availability, so it’s advisable to check with each property directly for the most accurate pricing information.

Costs and Tips

  • Accommodations: Costs vary from $100 to $300 per night depending on the chosen hotel.
  • Fuel: Plan for  approximately $150 to $200 for the entire trip, depending on your vehicle’s fuel efficiency.
  • Meals: Budget around $40 to $60 per person per day for meals.

1. Check the weather and road conditions before embarking on your road trip.

2. Pack a cooler with snacks and drinks for the journey.

3. Capture the scenic views with a camera or smartphone to document your adventure.

4. Consider renting a convertible for an even more immersive experience on the open roads.

5. Be flexible with your itinerary to allow for spontaneous detours and discoveries along the way.

Other Tips 

Other Tip #1:  Cell phone reception is poor. Especially after you pass Ellison Bay. Very little to be had!

Other Tip #2: The biggest grocery store you’ll find is Piggly Wiggly in Sister Bay

Other Tip #3: On the Way Up: Stop at Kopps (several locations near Milwaukee, one not far off I-43). Good custard and big burgers

Other Tip #4: My favorite thing to do: sit back, read a book, and relax and get into Lake Michigan to reap all the amazing benefits of a cold plunge.  You can easily become disconnected from the hustle and bustle of modern life. Just enjoy peace and quiet and serenity, that is sometimes hard to find in the city. 

Most important Other Tip #5: eat the corsica bread. Definitely eat the corsica bread and bring some home to your family

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