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Escape to Madison, WI: Your Ultimate Weekend Getaway Guide from Chicago

Updated: Nov 20, 2023



Madison, the capital of Wisconsin, is an easy 2-hour drive from the hustle and bustle of Chicago and is well worth a visit! With a strong identity as the home of the Badgers, it has a fantastic blend of urban sophistication and relaxed midwestern vibes.


My husband and I spent a lovely weekend there, enjoying the rich selection of fun outdoor activities and diverse cuisine. With Madison’s proximity to Chicago, it is perfectly situated for folks looking to escape the big city for a weekend.


Ten Must-Do Activities

Madison boasts many fun activities for all types of visitors and interests!


1. Olbrich Botanical Gardens: You will not be disappointed with your visit to the enchanting Olbrich Botanical Gardens, where exotic plants and landscapes provide a tranquil retreat. Be sure to also check their calendar for special events!

2. Dane County Farmers Market: Immerse yourself in the vibrant colors and flavors of the Dane County Farmers Market. You’ll find fresh produce and artisanal goods produced by the members behind the tables! There are four markets: Wednesday Market, Saturday Market on the Square, Holiday Market, and Late Winter Market. See dcfm.org for more info.

3. Wisconsin State Capitol/Capitol Square: Explore the architectural splendor of the Wisconsin State Capitol and take a leisurely walk around Capitol Square where there are many shops, cafes, and local events. If you’d like to tour the Capitol, there are free public tours on the hour meeting in the Rotunda.

4. State Street: State Street is lined with eclectic shops, boutiques, and eateries. It's the perfect place for a stroll or some fun retail therapy! Some great shops include Little Luxuries and Soap Opera.

5. BCycle (Madison By Bike): Madison is extremely bike-friendly, and if the weather is right, there is no better way to experience the city than by bike! Madison's network of BCycles (all electric) allows you to easily explore the city's bike-friendly paths and lakeside views.



6. UW-Madison Arboretum: Enjoy the serene beauty of the UW-Madison Arboretum, offering miles of walking and biking trails through diverse ecosystems. We also appreciated the land caretaker’s commitment to honoring the Ho-Chunk Effigy Mounds, which can be found in the area.

7. Hilldale Shopping Center: Indulge in upscale shopping and dining at Hilldale Shopping Center, an outdoor mall that combines fashion, food, and entertainment with both national retailers and local gems.

8. Enchanted Valley Acres: For a charming rural escape, visit Enchanted Valley Acres, a family-owned farm offering seasonal activities and a delightful country atmosphere.


9. Pheasant Branch Conservancy: Nature enthusiasts will love the Pheasant Branch Conservancy, a nature reserve with trails winding through prairies, woodlands, and wetlands.

10. Downtown Middleton: Just a short drive from Madison, Downtown Middleton boasts its own unique charm with boutique shops, local eateries, and a welcoming community atmosphere.


Places To Eat

Madison is home to multiple James Beard Award winners and nominees, and we were thoroughly impressed with all the delicious food we had!



1. Ahan: Indulge in the flavors of Southeast Asia at Ahan, where traditional dishes are given a modern twist in a stylish setting. Chef Jamie Hoang is a 2023 James Beard Rising Star Nominee.

2. Graze: For farm-to-table goodness, Graze is a must-visit, where you can enjoy locally sourced ingredients in creative and delicious dishes. Chef Tory Miller is a James Beard Award Winner.

3. Amara: If you are in the mood for contemporary coastal Italian food, look no further! Amara has a wide variety of delicious Italian staples and a great atmosphere.

4. Merchant: Located close to Capitol Square, Merchant offers a refined dining experience with a menu that highlights the finest ingredients and incredible craft cocktails.

5. Craftsman Table and Tap: Enjoy craft beers and upscale pub fare in a cozy, rustic atmosphere at Craftsman Table and Tap.


6. Cider Farm (Madison On Tap Craft Beverage Trail): Explore Madison's craft beverage scene with a visit to a local cider tasting room on the Madison On Tap Craft Beverage Trail. The Cider Farm has won multiple awards for its incredible ciders!

Where To Stay

There are many great hotel options in Madison. We stayed at Hyatt Place Madison/Downtown, and loved how close it was to all the city’s attractions!


Madison, WI, is a special city that combines cultural experiences, natural beauty, and culinary delights. Whether you're exploring the city's vibrant urban scene or seeking tranquility in its natural spaces, Madison promises a memorable weekend getaway!


This blog post was sponsored by Destination Madison. Opinions are my own.

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