Wisconsin

27 Jun 2025

Edit

Save

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
Remove Edit Reorder
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
Remove Edit Reorder
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
Remove Edit Reorder
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
Remove Edit Reorder
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
Remove Edit Reorder
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
Remove Edit Reorder
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
Remove Edit Reorder
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
Remove Edit Reorder
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
Remove Edit Reorder
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
Remove Edit Reorder
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.
Remove
Edit
Reorder
4.3
$$$$
The Al Ringling Brewing Co.
Located in a historic theatre in Baraboo near Devil's Lake, this brewpub offers house-made beers and pub fare in an unusual, ornate setting.
4.3
$$$$
Ishnala Supper Club
Remove
Edit
Reorder
8.5
$$$$
Ishnala Supper Club
Nestled in the woods overlooking Mirror Lake near Wisconsin Dells, Ishnala offers iconic supper club dining with panoramic views and unique mid-century decor.
8.5
$$$$
Frank’s Diner
Remove
Edit
Reorder
4.7
$$$$
Frank’s Diner
Housed in a vintage railcar in Kenosha, this classic diner serves up legendary breakfasts with an old-school, quirky atmosphere.
4.7
$$$$
The Rookery at Lagunitas Brewing Company
Remove
Edit
Reorder
The Rookery at Lagunitas Brewing Company
Situated inside the Chicago brewery, The Rookery combines creative pub eats with inventive brews in an industrial, lively setting.
Donny’s Glidden Lodge Restaurant
Remove
Edit
Reorder
4
$$$$
Donny’s Glidden Lodge Restaurant
Located on the Door County lakeshore, this retro-style supper club is known for hearty Midwestern cuisine and beautiful views of Lake Michigan.
4
$$$$

Hotels

The American Club, Kohler
Remove
Edit
Reorder
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
Remove
Edit
Reorder
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
Remove
Edit
Reorder
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
Remove
Edit
Reorder
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
Remove
Edit
Reorder
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

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
Visit Website
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
Visit Website

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
Visit Website
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
Sasha Colby: Stripped II
Sasha Colby: Stripped II
Doors at 7:00 pm | Show at 8:00 pm Ages 18+ 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...
Barrymore Theatre in Madison (23.24 mi)
18 Oct 2025
Visit Website
moe.
moe.
Doors at 7:00 pm | Show at 8:00 pm There are no elevators in the theatre. $1 from every ticket sold goes to Rock The Pink. As part of the American Cancer Society, Rock The Pink is a 501(c)(3) non-profit that is an industry-wide campaign to help end b...
Barrymore Theatre in Madison (23.24 mi)
19 Oct 2025
Visit Website
MANIA: The ABBA Tribute
MANIA: The ABBA Tribute
Doors at 6:30 pm | Show at 7:30 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)
23 Oct 2025
Visit Website

Travel Gems from Reddit

recommendation for a weekend getaway near Madison? Hi, here asking for good recommendations for a couple to enjoy a weekend together. i know i know, it is winter still and it ...
recommendation for a weekend getaway near Madison?
recommendation for a weekend getaway near Madison? Hi, here asking for good recommendations for a couple to enjoy a weekend together. i know i know, it is winter still and it ...
/r/madisonwi
View on Reddit
10 votes, 14 comments. Bestie and I turn 40 this year. We want to take a weekend vacation somewhere within a 5 hour drive, any direction. Door County
Weekend vacation ideas
10 votes, 14 comments. Bestie and I turn 40 this year. We want to take a weekend vacation somewhere within a 5 hour drive, any direction. Door County
/r/madisonwi
View on Reddit

I would recommend checking out High Cliff State Park on your way up. Its on lake Winnebago. We were only able to stop by for a few minutes but would have loved to have had tim...
One overnight getaway from Madison
I would recommend checking out High Cliff State Park on your way up. Its on lake Winnebago. We were only able to stop by for a few minutes but would have loved to have had tim...
/r/madisonwi
View on Reddit
Hi everyone, I moved to Madison (and the US) a couple of months ago. In the middle of September, my husband and I will be celebrating our wedding
Weekend getaway in Door County or Chicago?
Hi everyone, I moved to Madison (and the US) a couple of months ago. In the middle of September, my husband and I will be celebrating our wedding
/r/madisonwi
View on Reddit

Music for Your Journey

Rascal Flatts - Life is a Highway
Remove
Edit
Reorder
Rascal Flatts - Life is a Highway
A classic road trip anthem that's sure to energize your journey and set a carefree, adventurous mood.
Willie Nelson - On The Road Again - Live
Remove
Edit
Reorder
Willie Nelson - On The Road Again - Live
A timeless tune celebrating the excitement of traveling and exploring new places.
Rihanna - Shut Up And Drive
Remove
Edit
Reorder
Rihanna - Shut Up And Drive
An upbeat pop-rock song that adds fun and power to any drive.

Midwest Boyz - See It Through
Remove
Edit
Reorder
Midwest Boyz - See It Through
Celebrates Midwest charm and nostalgia, fitting for regional adventures.
Rusted Root - Send Me on My Way
Remove
Edit
Reorder
Rusted Root - Send Me on My Way
A cheerful song that perfectly captures the spirit of embarking on a travel adventure.
America - Ventura Highway
Remove
Edit
Reorder
America - Ventura Highway
Offers sunny, breezy vibes to keep the trip light and relaxing.
Fleetwood Mac - Go Your Own Way - 2004 Remaster
Remove
Edit
Reorder
Fleetwood Mac - Go Your Own Way - 2004 Remaster
An empowering, feel-good track about moving forward and embracing the unknown.
Tracy Chapman - Fast Car
Remove
Edit
Reorder
Tracy Chapman - Fast Car
Blends storytelling and catchy melodies for a reflective drive between destinations.
Edward Sharpe & The Magnetic Zeros - Home
Remove
Edit
Reorder
Edward Sharpe & The Magnetic Zeros - Home
A heartfelt tune that celebrates the joy of both travel and returning home.
Of Monsters and Men - Little Talks
Remove
Edit
Reorder
Of Monsters and Men - Little Talks
Energetic indie-pop song that keeps spirits high on the open road.

Your Trips Will Appear Here

10 Best Places for Weekend Getaway from Madison, WI

Weekend Getaway from Madison, WI: Top Destinations Overview

Recommended Activities

Wisconsin Dells

Devil's Lake State Park

Lake Geneva

Galena, Illinois

Milwaukee

Spring Green

New Glarus

Door County

Chicago, Illinois

Elkhart Lake

Restaurants

The Al Ringling Brewing Co.

The Al Ringling Brewing Co.

Ishnala Supper Club

Ishnala Supper Club

Frank’s Diner

Frank’s Diner

The Rookery at Lagunitas Brewing Company

The Rookery at Lagunitas Brewing Company

Donny’s Glidden Lodge Restaurant

Donny’s Glidden Lodge Restaurant

Hotels

The American Club, Kohler

The American Club, Kohler

The Maxwell Mansion

The Maxwell Mansion

Don Q Inn

Don Q Inn

Ironworks Hotel

Ironworks Hotel

Baker House Hotel

Baker House Hotel

Local Events & Happenings

SUGO

SUGO

Chris Fleming

Chris Fleming

Small Town Murder Podcast

Small Town Murder Podcast

Laurie Berkner: The Greatest Hits Solo Tour

Laurie Berkner: The Greatest Hits Solo Tour

Sasha Colby: Stripped II

Sasha Colby: Stripped II

moe.

moe.

MANIA: The ABBA Tribute

MANIA: The ABBA Tribute

Travel Gems from Reddit

recommendation for a weekend getaway near Madison?

Weekend vacation ideas

One overnight getaway from Madison

Weekend getaway in Door County or Chicago?

Music for Your Journey

Rascal Flatts - Life is a Highway

Rascal Flatts - Life is a Highway

Willie Nelson - On The Road Again - Live

Willie Nelson - On The Road Again - Live

Rihanna - Shut Up And Drive

Rihanna - Shut Up And Drive

Midwest Boyz - See It Through

Midwest Boyz - See It Through

Rusted Root - Send Me on My Way

Rusted Root - Send Me on My Way

America - Ventura Highway

America - Ventura Highway

Fleetwood Mac - Go Your Own Way - 2004 Remaster

Fleetwood Mac - Go Your Own Way - 2004 Remaster

Tracy Chapman - Fast Car

Tracy Chapman - Fast Car

Edward Sharpe & The Magnetic Zeros - Home

Edward Sharpe & The Magnetic Zeros - Home

Of Monsters and Men - Little Talks

Of Monsters and Men - Little Talks