Wisconsin

27 Jun 2025

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10 Best Places for Weekend Getaway from Madison, WI

Weekend Getaway from Madison, WI: Top Destinations Overview

Embark on an exciting weekend adventure with our selection of the top getaway destinations within a short drive from Madison, Wisconsin. Whether you're seeking thrills at the lively waterparks of Wisconsin Dells, breathtaking natural beauty at Devil’s Lake State Park, or lakeside luxury in Lake Geneva, there’s something for everyone. Delve into the historic charm of Galena, Illinois, enjoy the dynamic culture and lakeside views in Milwaukee, or experience world-class theatre and architectural wonders in Spring Green. Savor Swiss heritage and craft brews in New Glarus, explore quaint harbors and cherry orchards in Door County, or indulge in the vibrant urban offerings of Chicago. For a tranquil retreat, unwind by the sparkling shores of Elkhart Lake, where relaxation and recreation meet. Each destination offers a unique blend of nature, history, culture, and fun, promising an unforgettable weekend escape.

Recommended Activities

1
Wisconsin Dells
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Known as the 'Waterpark Capital of the World,' Wisconsin Dells offers a variety of indoor and outdoor waterparks, scenic boat tours, unique rock formations, and entertainment for all ages, making it a fun and exciting family-friendly getaway.
2
Devil's Lake State Park
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Renowned for its stunning 500-foot quartzite bluffs, crystal-clear lake, and miles of hiking trails, Devil's Lake State Park is perfect for outdoor enthusiasts seeking hiking, rock climbing, swimming, and breathtaking natural beauty.
3
Lake Geneva
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Lake Geneva is a charming resort town featuring a beautiful lake, lakeside beaches, boat tours, historic mansions, shopping, dining, and a vibrant arts scene, ideal for relaxation and recreation.
4
Galena, Illinois
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Galena is a picturesque town known for its well-preserved 19th-century architecture, charming Main Street with boutique shops and delicious eateries, rich history, and scenic bluffs, making it perfect for a relaxing and historic getaway.
5
Milwaukee
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Milwaukee offers vibrant city life with celebrated breweries, a beautiful lakefront, unique museums like the Milwaukee Art Museum, lively festivals, and diverse dining, providing an urban escape filled with culture and fun.
6
Spring Green
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Spring Green is famous for Frank Lloyd Wright’s iconic Taliesin estate, the American Players Theatre, and stunning natural scenery, making it a cultural and artistic retreat surrounded by rolling hills and beauty.
7
New Glarus
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New Glarus, known as 'America’s Little Switzerland,' offers charming Swiss-style architecture, unique shops, delicious bakeries, the world-famous New Glarus Brewing Company, and lively Swiss festivals, making it a delightful and unique cultural escape.
8
Door County
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Door County boasts stunning shorelines along Lake Michigan, charming harbor towns, beautiful state parks, cherry orchards, art galleries, and a wealth of outdoor activities, making it a top destination for relaxation and adventure.
9
Chicago, Illinois
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Chicago is a world-class city with incredible attractions including iconic architecture, award-winning restaurants, museums, vibrant neighborhoods, cultural events, music, and shopping—perfect for an exciting urban getaway.
10
Elkhart Lake
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Elkhart Lake is known for its crystal-clear lake, charming small-town atmosphere, resort spas, water sports, and the world-famous Road America racing track, making it an ideal destination for relaxation, outdoor fun, and motorsports enthusiasts.

Restaurants

The Al Ringling Brewing Co.
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4.3
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The Al Ringling Brewing Co.
Located in a historic theatre in Baraboo near Devil's Lake, this brewpub offers house-made beers and pub fare in an unusual, ornate setting.
4.3
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Ishnala Supper Club
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8.5
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Ishnala Supper Club
Nestled in the woods overlooking Mirror Lake near Wisconsin Dells, Ishnala offers iconic supper club dining with panoramic views and unique mid-century decor.
8.5
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Frank’s Diner
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4.3
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Frank’s Diner
Housed in a vintage railcar in Kenosha, this classic diner serves up legendary breakfasts with an old-school, quirky atmosphere.
4.3
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The Rookery at Lagunitas Brewing Company
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The Rookery at Lagunitas Brewing Company
Situated inside the Chicago brewery, The Rookery combines creative pub eats with inventive brews in an industrial, lively setting.
Donny’s Glidden Lodge Restaurant
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4
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Donny’s Glidden Lodge Restaurant
Located on the Door County lakeshore, this retro-style supper club is known for hearty Midwestern cuisine and beautiful views of Lake Michigan.
4
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Stay Recommendations

The American Club, Kohler
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The American Club, Kohler
A luxury resort in Kohler with a fascinating history as former immigrant worker housing, now offering upscale amenities and themed rooms.
The Maxwell Mansion
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4.7
The Maxwell Mansion
A boutique hotel in Lake Geneva featuring opulent rooms, a speakeasy, and secret gardens, offering a blend of history and mystery.
4.7
Don Q Inn
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4.2
Don Q Inn
Near Dodgeville, this quirky hotel is famous for themed rooms—think a Boeing 727 suite, a medieval chamber, and more for a whimsical stay.
4.2
Ironworks Hotel
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4.6
Ironworks Hotel
Located on the banks of the Rock River in Beloit, this boutique hotel combines industrial-chic style with unique décor inspired by the city’s ironworking heritage.
4.6
Baker House Hotel
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4.2
Baker House Hotel
This historic mansion in Lake Geneva offers lavish, themed suites and lakeside elegance, transporting guests to the Gilded Age.
4.2

Local Events & Happenings

OVERTIME: The Long Way Home Tour w/ KRIZZ KALIKO in Beaver Dam
OVERTIME: The Long Way Home Tour w/ KRIZZ KALIKO in Beaver Dam
Independent music powerhouse Overtime embarks on The Long Way Home Tour, set to kick off in support of his upcoming album of the same name. Backed by The Blue Collar Soldiers Band, Overtime will bring his signature blend of country, rock, and rap to ...
Stormy's Music Venue in Beaver Dam (20.16 mi)
16 Aug 2025
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Kris Crow Band
Kris Crow Band
https://www.facebook.com/kriscrowbandEight of the most inspiring, professional musicians in the region getting together to bring joy, funkiness and movability to the people.
RallyPoint in Oconomowoc (22.01 mi)
16 Aug 2025
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SUGO
SUGO
https://www.facebook.com/profile.php?id=100087707371402sugotheband.comSugo! The retro-funk band out of Milwaukee, WI🤌🏻
RallyPoint in Oconomowoc (22.01 mi)
18 Oct 2025
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Robert Cray Band
Robert Cray Band
Doors at 7:00 pm | Show at 8:00 pm There are no elevators in the theatre. Advance tickets can be purchased online or at The Sylvee box office. Once the doors have opened, if tickets are still available, they can be purchased at the Barrymore Theatre....
Barrymore Theatre in Madison (23.24 mi)
13 Aug 2025
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Chris Fleming
Chris Fleming
Doors at 7:00 pm | Show at 8:00 pm There are no elevators in the theatre. Advance tickets can be purchased online or at The Sylvee box office. Once the doors have opened, if tickets are still available, they can be purchased at the Barrymore Theatre....
Barrymore Theatre in Madison (23.24 mi)
13 Sep 2025
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Small Town Murder Podcast
Small Town Murder Podcast
Doors at 7:00 pm | Show at 8:00 pm There are no elevators in the theatre. Advance tickets can be purchased online or at The Sylvee box office. Once the doors have opened, if tickets are still available, they can be purchased at the Barrymore Theatre....
Barrymore Theatre in Madison (23.24 mi)
20 Sep 2025
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Laurie Berkner: The Greatest Hits Solo Tour
Laurie Berkner: The Greatest Hits Solo Tour
Doors at 10:00 am | Show at 11:00 am Infants under 1 year old who will be sitting on a lap do not need a ticket. All other guests will need a ticket. There are no elevators in the theatre. Advance tickets can be purchased online or at The Sylvee box ...
Barrymore Theatre in Madison (23.24 mi)
27 Sep 2025
Visit Website