27 Jun 2025

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10 Best Places for Weekend Trips From Kenosha, WI

Weekend Trip Itinerary Overview: Best Getaways from Kenosha, WI

Embark on an unforgettable weekend adventure with this curated list of the ten best destinations within a short drive from Kenosha, WI. Whether you seek vibrant city experiences, picturesque lake towns, historic sites, or immersive nature escapes, there’s something on this itinerary for every traveler. Explore the bustling streets of Chicago and Milwaukee for world-class dining, museums, and entertainment. Unwind at the scenic shores of Lake Geneva or discover the serene beauty of Kettle Moraine State Forest and Devil’s Lake State Park—perfect for hiking, picnicking, and outdoor fun. Venture to Madison, a lively capital with beautiful lakes and a bustling downtown, or step back in time in Galena, where charming 19th-century architecture creates a storybook atmosphere. Racine offers a relaxing lakefront and local treats, while Starved Rock State Park in Illinois amazes with dramatic canyons and waterfalls. Don’t miss Oak Park’s architectural wonders, especially its concentration of Frank Lloyd Wright homes. Each destination provides its unique charm and a refreshing change of scenery, making your weekends truly memorable.

Recommended Explorations

1
Milwaukee, WI
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Milwaukee offers a vibrant arts scene, delicious breweries, the scenic Lake Michigan waterfront, and unique attractions like the Milwaukee Art Museum and Harley-Davidson Museum.
2
Lake Geneva, WI
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Lake Geneva is known for its beautiful lake views, historic estates, water sports, charming downtown, and relaxing resorts—perfect for a peaceful getaway.
3
Chicago, IL
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Chicago boasts world-class museums, impressive architecture, diverse restaurants, iconic attractions like Millennium Park and Navy Pier, and a dynamic city atmosphere ideal for adventure.
4
Devil's Lake State Park, WI
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Devil's Lake State Park features stunning quartzite bluffs, scenic hiking trails, crystal-clear lakes, and opportunities for rock climbing, swimming, and picnicking in a beautiful natural setting.
5
Starved Rock State Park, IL
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Starved Rock State Park is known for its dramatic canyons, waterfalls, lush forests, and diverse wildlife, making it a top spot for hiking, sightseeing, and enjoying nature.
6
Madison, WI
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Madison offers a blend of vibrant culture, beautiful lakes, outdoor recreation, a lively farmers' market, unique museums, and the stunning Wisconsin State Capitol.
7
Racine, WI
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Racine features a beautiful lakefront, historic architecture, family-friendly beaches, and the famous Racine Danish Kringle, offering a charming small-city experience.
8
Galena, IL
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Galena is renowned for its well-preserved 19th-century buildings, quaint downtown, scenic river views, and unique shops, making it a picturesque and historic getaway.
9
Kettle Moraine State Forest, WI
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Kettle Moraine State Forest provides diverse hiking and biking trails, glacial landscapes, peaceful lakes, and excellent camping, perfect for outdoor enthusiasts and nature lovers.
10
Oak Park, IL
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Oak Park is famous for its stunning Frank Lloyd Wright architecture, vibrant arts community, historic neighborhoods, and easy access to Chicago, making it ideal for architecture enthusiasts and culture seekers.

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Ironworks Hotel
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4.6
Ironworks Hotel
This boutique hotel in Beloit, WI features industrial-chic decor inspired by the city's manufacturing history, offering a distinctive and stylish stay.
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4.6
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The Pfister Hotel (Milwaukee)
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The Pfister Hotel (Milwaukee)
A Milwaukee landmark since 1893, this opulent hotel is renowned for its Victorian art collection, rooftop lounge, and historic grandeur.
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Graduate Madison
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8.2
Graduate Madison
A quirky, collegiate-themed hotel in downtown Madison, filled with nostalgic nods to university life and unique local touches.
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8.2
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Mission House Bed & Breakfast
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Mission House Bed & Breakfast
Housed in an 1850s church in Galena, IL, this B&B offers a truly unique experience with beautiful stained-glass windows and historical charm.
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The Abbey Resort
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4.1
The Abbey Resort
Nestled on Lake Geneva’s shore, this resort features a nautical theme, full-service spa, and plush amenities, making it a standout for relaxation and lakeside views.
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4.1
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