16 Fun and Relaxing Weekend Getaways From Milwaukee

Map of Weekend Getaways from Milwaukee

This article may contain links from our affiliate partners.  As an Amazon Associate, we earn money from qualifying purchases. Please read our disclosure to find out more.

Milwaukee is our hometown, and we love enjoying all it offers. But sometimes, taking a little weekend trip from Milwaukee to explore something new feels refreshing.

Below we have listed several options for weekend trips from Milwaukee categorized by driving time from the city. 

So whether you are looking for a short or a little bit longer drive, we have some great options!

Let’s find that perfect weekend trip from Milwaukee!

Weekend Getaways from Milwaukee: 1 Hour or Less

Map of Milwaukee area with driving distance of 1 hour away highlighted
Map made with Smappen.com

Sheboygan, WI

Sheboygan, WI, is a beautiful city on the shores of Lake Michigan. It’s a great place to spend a weekend getaway, as there are plenty of things to do and see. Some highlights include the John Michael Kohler Arts Center (the bathrooms are a must-see), the Kohler-Andrae State Park, shopping along 8th street, and learning to surf.

Sheboygan is known as the “Malibu of the Midwest.” Surfing in Sheboygan is year-round, but the waves are typically the best from August to April. You can rent gear from Eos Surf Shop if you are a seasoned surfer. They also offer lessons for both surfing and kite surfing. 

Image of Neon Sign that reads "Malibu of the Midwest"

The Kohler-Andrae State Park is a beautiful park on the shores of Lake Michigan. It’s a great place to go for a hike, swim, or just enjoy the views.

Downtown Sheboygan is a great place to walk around and explore. There are plenty of shops and restaurants to check out, and it’s a great place to people-watch. Mural hunting is also a favorite pass time for weekend travelers.

Where to stay: Lake View Mansion Bed & Breakfast

Lake View Mansion Bed & Breakfast is a beautiful bed and breakfast in downtown Sheboygan. Rooms are comfortable and spacious, and the staff is friendly and welcoming. The bed and breakfast also features a delicious breakfast. It’s perfect for a weekend getaway to Sheboygan.

Sheboygan is a great option if you’re looking for a weekend getaway close to Milwaukee. It’s a beautiful city with plenty to do and see.

Related Post: Fun Things to Do on Your Next Sheboygan Adventure

Lake Country – Western Waukesha County

Lake Country is a simply gorgeous area of Wisconsin. Located west of Milwaukee in Waukesha County, the area has hiking and biking trails, golf courses, wineries, breweries, and many lakes. It’s a great place to get away for the weekend if you love the outdoors.

There are plenty of trails to explore in Lake Country, including nearby Lapham Peak State Forest for hiking. Or plenty of biking trails for those who like to adventure on two wheels.  

And a visit to Lake Country wouldn’t be complete without some time spent on the water. You can rent pontoons, kayaks, or paddle boards or bring your own to explore the many lakes of Lake Country. 

For indoor entertainment, try the Lake Country Playhouse. This theater hosts a variety of shows throughout the year, so there’s sure to be something that interests you.

Where to Stay: The Delafield Hotel or an Airbnb on a lake

The Delafield Hotel is an upscale hotel located on a beautiful golf course. There is a delicious restaurant on-site, and you’ll be close to all the fun in Lake Country. 

Cedarburg, WI

Cedarburg is a charming city located just north of Milwaukee, full of boutique shops, art galleries, and bakeries. If you love shopping, you’ll be in heaven in Cedarburg.

And if you love biking, you can take the Interurban Trail from Cedarburg to Port Washington and beyond. 

Cedarburg is also home to several festivals throughout the year. The most popular is the Strawberry Festival, which takes place in the summer. Other festivals include the Wine and Harvest Festival, the Winter Festival, and the Cedarburg ArtFair.

Each of these festivals has its own special charm. For example, the Wine and Harvest Festival features a grape stomping competition, while the Strawberry Festival has a strawberry shortcake eating contest.

Where to Stay: Washington House Inn

The Washington House Inn is a historic bed and breakfast. This beautiful inn has welcomed travelers since the mid-1800s, and its antique furnishings and cozy fireplaces make it the perfect place to stay for a romantic weekend getaway.

Lake Geneva, WI

Lake Geneva is a beautiful city located in southeastern Wisconsin. It’s a popular destination for both tourists and locals alike. The city is situated on the shores of Lake Geneva, and there are plenty of things to do in the area, including swimming, boating, fishing, and hiking.

The downtown area is full of shops and restaurants. There is also a Thursday farmer’s market

Check out the Geneva Lake Museum if you’re looking for something to do on a rainy day. This museum features exhibits on the history of the lake and the city.

Where to Stay: The Lazy Cloud Inn

The Lazy Cloud Inn is the perfect place to stay for a romantic weekend getaway. The rooms are comfortable and spacious, and the staff is warm and welcoming. The breakfast is delicious, and you can enjoy it in your room if you prefer.

Kohler, WI

Kohler is a small village located in southeastern Wisconsin. It’s home to many art galleries, shops, and restaurants. And, of course, it’s also home to the Kohler Company, known for its high-quality plumbing fixtures.

If you’re looking for things to do, head to the Kohler Design Center. This center features exhibits on the history of the Kohler Company, as well as various interactive displays. You can also tour the factory, which is a great way to see how the fixtures are made.

Where to Stay: The American Club Resort

The American Club Resort is a luxury hotel located in Kohler. Rooms are spacious and well-appointed, with the staff attentive and professional. The resort also features an indoor pool, spa, and fitness center. If you’re looking for a relaxing weekend of pampering, this is your weekend getaway. 

Weekend Getaways from Milwaukee: 2 Hours or Less

Map of Wisconsin with driving distance of 2 hours or less highlighted from Milwaukee
Map made with Smappen.com

Chicago, IL

Chicago is probably one of the most famous and popular destinations for weekend trips from Milwaukee. After all, it is the third-largest city in the United States. There is so much to see and do in Chicago that you could easily spend a week and not get bored. Plus, you can take the Amtrak train there directly from the Milwaukee station, making it super easy to get there.

Some must-see attractions in Chicago include Millennium Park, The Art Institute of Chicago, The Field Museum, and Shedd Aquarium. And that’s just scratching the surface. If you’re a fan of shopping, you’ll be happy to know that Chicago is home to various shops, from high-end boutiques to discount stores.

Where to Stay: The Palmer House Hilton

The Palmer House Hilton is a historic hotel located in the heart of downtown Chicago. This luxury hotel features an array of amenities, including an on-site spa, a fitness center, and a business center. The rooms are spacious and elegant, and the staff is attentive and professional.

Madison, WI

Madison is the capital of Wisconsin and is just a little over an hour’s drive from Milwaukee. 

This vibrant city is home to a variety of attractions, including the State Capitol, the University of Wisconsin-Madison, and the Wisconsin Historical Museum. If you’re a fan of the outdoors, you’ll be happy to know that Madison is situated on an isthmus between two lakes, so there are plenty of swimming, hiking, and boating opportunities.

Madison is also a great place to eat, as it is home to various restaurants, from casual cafes to fine dining establishments. The UW-Madison Union Terrace is a must-do to enjoy beautiful Lake Mendota while eating an ice cream cone or enjoying a drink. 

Where to Stay: The Edgewater

The Edgewater is a hotel located on the shores of Lake Mendota in downtown Madison. The rooms are comfortable and spacious, and the staff is friendly and helpful. The hotel also features several amenities, including an indoor pool, a fitness center, and a business center. 

Spring Green, WI

Spring Green is a small town located in south-central Wisconsin. The town is best known for being the home of Taliesin, the former estate of famed architect Frank Lloyd Wright. Today, Taliesin is a museum and tourist attraction, and it is one of the main reasons why people visit Spring Green.

In addition to Taliesin, Spring Green is also home to many other attractions, including the House on the Rock, Governor Dodge State Park, Cave of the Mounds, and the American Player’s Theatre. The town lies in the scenic Wisconsin River Valley, so there are plenty of hiking, biking, and canoeing opportunities.

The House on the Rock was designed and built by Alex Jordan, and it is known for its eclectic architecture and unusual collection of artifacts. The house is open to the public, which is one of the main reasons people visit Spring Green.

Governor Dodge State Park is home to various hiking trails, a lake, and a campground, while Cave of the Mounds is a National Natural Landmark in the town of Blue Mounds. The cave is known for its unique rock formations and abundance of fossils.

After a full day of hiking, be sure to stop by The American Player’s Theatre, a professional repertory theatre company that produces a variety of plays, from classics to contemporary works.

Where to stay: Silver Star Inn 

The Silver Star Inn is a cozy bed and breakfast on six acres of beautiful land in the driftless area. It features a variety of amenities, including a hummingbird garden. The rooms are comfortable and well-appointed, and the staff is friendly and helpful. As such, it’s the perfect place to stay if you’re looking for a relaxing weekend getaway in Spring Green.

New Glarus, WI

New Glarus is a small town located in the driftless area of southwest Wisconsin. The town is best known for its Swiss heritage and is home to several Swiss-themed attractions, including the New Glarus Brewing Company, the Swiss Alps Resort, and the Chalet Landhaus Inn. 

New Glarus is in the scenic Wisconsin River Valley, so there are plenty of hiking, biking, and canoeing opportunities. You can bike along the Sugar River State Trail or do a lazy float down the Sugar River.  

Check out nearby Paoli for more shops and activity options. 

Where to Stay: Chalet Landhaus Inn

For a culturally immersive experience, there’s no better place to stay than the Chalet Landhaus Inn. The inn is located in the heart of downtown New Glarus and features many Swiss-themed amenities, including a Swiss restaurant, a fondue parlor, and a spa. The rooms are comfortable and spacious, and the staff is friendly and helpful. 

Wisconsin Dells, WI

Wisconsin Dells is best known for its water parks, which attract visitors from all over the Midwest – and even the world! In addition to its water parks, Wisconsin Dells is also home to several other attractions, including the Timbavati Wildlife Park and the Tommy Bartlett Exploratory. 

The Timbavati Wildlife Park is home to many exotic animals, as well as a variety of educational exhibits. And the Tommy Bartlett Exploratory is a hands-on science museum perfect for kids.

But Wisconsin Dells is more than water parks and tourist attractions. The scenery around the Dells is some of the best in the state. Immerse yourself in the scenery by getting on the water. There are several options for boat tours and kayaking. And don’t miss out on taking a boat tour to Witches Gulch

The Wisconsin Dells area is also home to some of the best supper clubs in Wisconsin. If supper clubs are your thing, check out The Del Bar or Ishnala

Related Post: Wisconsin Supper Club Map: Digital Map for On-the-Go Access

Where to stay: The Wilderness Resort

The Wilderness Resort is one of the most popular resorts in Wisconsin Dells, and it’s easy to see why. The resort features a water park, an indoor water park, a golf course, and various other amenities. 

There’s a spa and a fitness center for adults. And for kids, there’s an arcade and a playground. This is the place for you if you’re looking for a resort with it all.

Related Wisconsin Posts:
Wisconsin Winter Getaway Ideas to Cure the Winter Blues
Best Places to View Fall Colors in Wisconsin
Best Wisconsin State Parks
Wisconsin Waterfall Map + 2 Waterfall Tour Itineraries

Waupaca – Chain O Lakes

Waupaca is a small town located in central Wisconsin. The town is situated in an area known as the Chain O Lakes and is home to several parks and recreational areas. The Chain O Lakes brings people to the area and features various activities, including swimming, fishing, boating, and hiking.

The Ice Age National Scenic Trail runs through the area giving visitors ample options for hikes. 

In addition to its outdoor activities, Waupaca is also home to many shops and restaurants. The town’s main street is lined with a variety of boutiques and cafes, and several antique shops are located in the downtown area. The area’s favorites are Little Fat Gretchen’s, Clear Water Harbor Restaurant, and Wheelhouse for pizza.

Where to stay: The Crystal River Inn

The Crystal River Inn is a historic bed and breakfast located in the downtown area. It features a number of rooms with antique furnishings, and it offers a complimentary breakfast each morning. In addition, the inn has lovely common areas, including a library and a sitting room.

Weekend Getaways from Milwaukee – 3 Hours or Less

Map of Wisconsin with driving distance of 3 hours or less highlighted from Milwaukee
Map made with Smappen.com

Starved Rock State Park – Utica, Illinois

Starved Rock State Park is located about 90 minutes from Milwaukee in Utica, Illinois. The park is home to several hiking trails which feature canyons and waterfalls. In addition, the park has a variety of wildlife, including eagles, falcons, and deer.

Historical tours and hikes are offered at the park, and several lodges and cabins are located within the park. Starved Rock is best known for its magnificent fall color displays in October.

Where to stay: The Starved Rock Lodge

The Lodge at Starved Rock is a historic lodge built in the 1920s. It features rooms and suites, as well as common areas, such as a library, a game room, and a dining room. The lodge also has an outdoor pool on the state park ground so that you can experience an immersive nature experience.

Indiana Dunes National Park – Chesterton, Indiana

Indiana Dunes National Park is located about two hours from Milwaukee in Chesterton, Indiana. The park is home to 15 miles of beaches along Lake Michigan, as well as a variety of hiking trails. In addition, the park has several sand dunes, which are perfect for hiking and exploring.

The park also offers a variety of ranger-led programs, including hikes, Junior Ranger programs, and nature walks. In addition, the park has lodges and cabins located within its boundaries.

Where to stay: At Home in the Woods

At Home in the Woods is a cozy bed and breakfast located just outside the national park. It offers a variety of rooms and common areas, such as a living room and a dining room. The bed and breakfast also has an outdoor pool and hot tub, so you can relax after a long day exploring the park.

Sturgeon Bay, WI

Sturgeon Bay is a small town located in northeastern Wisconsin. The town on the western shores of Lake Michigan is home to several parks and recreational areas. 

Its location at the beginning of the Door County Peninsula makes it an excellent option for those wanting a Door County experience without having to drive all the way up the peninsula. 

There are many great options for things to do, such as the Door County Winery and Distillery. It is also home to one of the most scenic parks in Wisconsin, Cave Point County Park.

The Door County Maritime Museum is the most popular spot in town. It features a variety of exhibits, including a shipwreck exhibit and a lighthouse exhibit.

Where to Stay: Glidden Lodge Beach Resort

Glidden Lodge Beach Resort is a perfect place to call home while exploring Sturgeon Bay. With its location directly on Lake Michigan, it’s one of the most picturesque places. 

It features a variety of rooms and suites. And it has amenities such as an indoor pool, a game room, and a dining room. The lodge also has a private beach to enjoy the lakefront views.

And the Glidden Lodge Restaurant is not to be missed. It has a gorgeous view of the lake and is one of the best supper clubs in Wisconsin

Related Post: Things to Do in Sturgeon Bay

Sparta, WI

Sparta, WI, is a bikers paradise. It’s known as the “Bikers Capital of America” because one of the first rail-to-trails bike paths is located between Elroy and Sparta. 

The Elroy-Sparta Trail is one of the most popular trails in the country. It’s a 32.5-mile trail with three rock tunnels to pass through and connects five towns. 

If you like biking, this is the weekend getaway for you. 

Where to Stay: Justin Trails Resort

Justin Trails Resort is located in the small town of Sparta, Wisconsin. The resort is on 200 acres of wooded land and offers various activities, such as hiking, biking, and cross-country skiing. In addition, the resort has an indoor pool, a game room, and a dining room.

Justin Trails is the perfect spot for an all-in-one experience where you won’t feel the need to leave the resort.

Galena, IL

Finally, we come to Galena, IL. Galena is located about three hours from Milwaukee in northwestern Illinois. It’s a historic town situated in a beautiful setting with rolling hills and picturesque views.

The downtown streets are lined with shops and restaurants. There are also a variety of historic buildings, such as the Ulysses S. Grant Home

Where to Stay: The Aldrich Guest House

The Aldrich Guest House is a bed and breakfast located in downtown Galena. The house was built in 1857 and has been updated and modernized to provide all the amenities and comforts of home.

The rooms at the Aldrich are furnished with antiques, each with its unique charm. The guest house is within walking distance of shops and restaurants and all of Galena’s historic sites.

Related Milwaukee Posts:
Best Craft Breweries in Milwaukee
Best Cheap Eats in Milwaukee
Best Casual Restaurants in Milwaukee

Join our newsletter!

Don’t miss out on our top tips for adventuring in the Upper Midwest! 

More To Explore