Pack your bags, grab your map, and get ready to discover the best weekend trips from Milwaukee! Whether you’re looking for relaxation by the lake, exploring charming small towns, or diving into vibrant city life, there are plenty of options to suit every traveler’s taste!
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Table of Contents
Map of Weekend Trips from Milwaukee
Sometimes it’s easier to plan your weekend getaway from a birds-eye view. Here’s a map showing all the best weekend trips from Milwaukee!
Best Weekend Getaways from Milwaukee
Okay, let’s dive in. From adventurous getaways to relaxing trips, this list has something for everyone!
1. Lake Geneva, Wisconsin
- Distance from Milwaukee: 50 miles
- Best for: Relaxation and water activities
Lake Geneva is a popular destination for those seeking relaxation and water activities. Spend your day on the lake with activities like boating, paddleboarding, or simply lounging on the beach.
Explore the historic downtown area with its boutique shops and dining options. For a unique experience, take a boat tour to see the lavish estates along the shoreline.
Dining options include Simple Café for breakfast and The Grandview Restaurant for dinner with a lakeside view. The town is walkable, but a car is recommended for exploring the surrounding areas.
Find Places to Stay in Lake Geneva!
2. Sheboygan, Wisconsin
- Distance from Milwaukee: 50 miles
- Best for: Beach lovers and art enthusiasts
Sheboygan is known for its beautiful beaches, art scene, and vibrant community events. Visit Kohler-Andrae State Park for beachcombing and hiking along the sand dunes.
The John Michael Kohler Arts Center offers contemporary art exhibits and performances.
Dining options include the popular Il Ritrovo for wood-fired pizzas and Field to Fork for fresh, local cuisine. Sheboygan is easy to navigate by car, with plenty of parking available near its main attractions.
Find Places to Stay in Sheboygan!
3. Kohler, Wisconsin
- Distance from Milwaukee: 55 miles
- Best for: Luxury and relaxation
Kohler is synonymous with luxury and relaxation, thanks to the renowned American Club Resort. Pamper yourself at the Kohler Waters Spa or play a round of golf at the Whistling Straits course.
For a bite to eat, experience the exquisite cuisine at The Immigrant Restaurant or enjoy a casual meal at the Horse & Plow.
Find Places to Stay in Kohler!
4. Madison, Wisconsin
- Distance from Milwaukee: 80 miles
- Best for: Culture and lakeside activities
Madison, the state capital, offers a unique blend of cultural attractions and outdoor activities. Visit the Wisconsin State Capitol, with its beautiful architecture and free guided tours.
The University of Wisconsin-Madison campus features the Chazen Museum of Art and the picturesque Memorial Union Terrace.
Enjoy farm-to-table dining at restaurants like Graze or grab a bite at the Dane County Farmers’ Market.
Lake Monona and Lake Mendota provide opportunities for boating, fishing, and scenic strolls. Madison’s bike-friendly paths make it easy to get around.
Find places to stay in Madison!
5. Chicago, Illinois
- Distance from Milwaukee: 90 miles
- Best for: City enthusiasts
Chicago is a bustling metropolis known for its towering skyscrapers, world-class museums, and vibrant culinary scene.
Start your day at Millennium Park, home to the iconic Cloud Gate sculpture (also known as “The Bean”). For art lovers, the Art Institute of Chicago offers an extensive collection of works spanning centuries.
Enjoy deep-dish pizza at Lou Malnati’s or head to the West Loop for a variety of trendy dining options. Don’t miss the Magnificent Mile for shopping and Navy Pier for entertainment and stunning lake views.
Chicago’s public transportation makes it easy to navigate but be prepared for busy streets and parking challenges.
Find places to stay in Chicago!
6. Rockford, Illinois
- Distance from Milwaukee: 90 miles
- Best for: Gardens and museums
Rockford offers a variety of attractions, including the beautiful Anderson Japanese Gardens, Rock Cut State Park, and the Burpee Museum of Natural History.
The city’s downtown area features shops, restaurants, and entertainment venues. Dining options include Abreo for modern American cuisine and Lino’s for classic Italian dishes.
Find Places to Stay in Rockford
7. Green Bay, Wisconsin
- Distance from Milwaukee: 120 miles
- Best for: Sports fans and family activities
Green Bay is known for its rich sports heritage and family-friendly attractions. Start your visit with a tour of Lambeau Field, home of the Green Bay Packers, and explore the adjacent Packers Hall of Fame.
For family fun, head to the Bay Beach Amusement Park or the NEW Zoo & Adventure Park. Dining options include Titletown Brewing Company and Hinterland Brewery.
Find Places to Stay in Green Bay, WI
8. Door County, Wisconsin
- Distance from Milwaukee: 150 miles
- Best for: Nature lovers and small-town charm
Door County is a picturesque region known for its charming small towns, scenic waterfronts, and outdoor activities. Explore the quaint shops and galleries in Fish Creek and Ephraim, then head to Peninsula State Park for hiking, biking, and breathtaking views of Green Bay.
For dining, try Al Johnson’s Swedish Restaurant, where goats graze on the roof, or indulge in fresh fish at Waterfront Restaurant. Kayaking, sailing, and visiting local wineries are also popular activities. Door County is best visited with a car to fully explore its spread-out attractions.
Find Places to Stay in Door County!
9. Galena, Illinois
- Distance from Milwaukee: 150 miles
- Best for: Historic tours and scenic views
Galena offers a charming escape with its well-preserved 19th-century buildings and scenic countryside. Stroll down Main Street to visit antique shops, art galleries, and historic sites like the Ulysses S. Grant Home.
Outdoor enthusiasts can enjoy hiking and wine tasting at local vineyards. Recommended dining spots include Fritz and Frites for German-French cuisine and Log Cabin Steakhouse for a hearty meal. Galena’s compact downtown is best explored on foot, though having a car allows for easier access to outlying attractions.
Find Places to Stay in Galena!
10. Saugatuck, Michigan
- Distance from Milwaukee: 140 miles (including ferry ride)
- Best for: Arts and beach activities
Saugatuck is an artsy town known for its beautiful beaches and vibrant art scene. Spend your day exploring local galleries, enjoying a dune ride, or relaxing on Oval Beach.
Dining options include The Southerner for comfort food and Everyday People Café for a fine dining experience. Saugatuck is walkable, but having a car allows for easier exploration of the surrounding areas and beaches.
Find Places to Stay in Saugatuck!
11. Starved Rock State Park, Illinois
- Distance from Milwaukee: 180 miles
- Best for: Hiking and nature adventures
Starved Rock State Park is a haven for nature lovers, offering beautiful canyons, waterfalls, and scenic overlooks. Hike the extensive trail system to see the park’s highlights, such as St. Louis Canyon and LaSalle Canyon.
Pack a picnic or dine at the Starved Rock Lodge for a rustic meal. Nearby, you can explore the town of Utica, which offers quaint shops and additional dining options like Duffy’s Tavern.
Find Places to Stay near Starved Rock State Park!
12. Taylors Falls, WI
- Distance from Milwaukee: 310 miles
- Best for: Hikers, Wine-lovers, and Unique fun!
Taylors Falls offers a delightful blend of natural beauty and outdoor adventure, making it an ideal weekend getaway from Milwaukee.
Nestled along the St. Croix River, this charming town is perfect for hiking, boating, and exploring scenic state parks. Visit Interstate State Park for stunning rock formations and picturesque trails, or take a riverboat cruise to soak in the breathtaking views.
For dining, enjoy a meal at The Drive-In Restaurant, a local favorite known for its classic American fare and nostalgic ambiance (you can even play a round of mini-golf here). Or, you can head down the road a bit to check out the charming Dancing Dragon Winery and Vineyard.
Don’t forget to stop by the Folsom House for a glimpse into the area’s history or the nearby Fawn-De-Rosa to meet some cut new deer friends!
Find Places to Stay near Taylors Falls!
13. Bayfield, WI (& Madeline Island)
- Distance from Milwaukee: 350 miles
- Best for: Relaxation and Kayaking
Bayfield, located on the shores of Lake Superior, is the gateway to the Apostle Islands National Lakeshore. Enjoy kayaking through sea caves, sailing, and exploring the beautiful islands.
Stroll through the charming downtown area, filled with boutique shops and art galleries. Don’t miss dining at The Pier Plaza, which offers fresh, locally sourced meals in a cozy atmosphere.
Bayfield is also known for its orchards and berry farms, perfect for picking your own fruit and enjoying homemade treats.
And, if you have extra time, hop on the ferry to the charming Madeline Island where you can do some more shopping, beach days, or hikes!
Find Places to Stay in Bayfield!
Weekend Getaways from Milwaukee Recap!
There ya have it! 13 exciting weekend trips from Milwaukee. Start planning your next relaxing weekend getaway today!
To help your planning, here’s a printable weekend guide planner!
Tip! Make sure to follow me on Instagram for more USA weekend getaways and dog-friendly adventures!
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