Madison Magic: Crafting Your Perfect Madison, WI Bucket List

Located between two sparkling lakes, Madison, Wisconsin, offers a vibrant blend of natural beauty, cultural attractions, and culinary delights. Whether you’re a local, a future resident looking for homes, or a visitor passing through, we have an excellent bucket list for you. Here’s our curated selection of must-do activities in Madison, all compiled into a comprehensive bucket list.

Explore State Street

State Street is conveniently located, between the Wisconsin State Capitol, and the University of Wisconsin-Madison. Packed with restaurants, shops, museums, music, and beautiful views, this pedestrian-friendly street is the heart of downtown Madison. 

“Take a stroll down State Street, where you will find some of the area’s best shopping, dining, and entertainment,” says Brian Lee from Eat Drink Madison.  “Head to the University of Wisconsin Memorial Union Terrace, a place to enjoy Babcock ice cream or a brat on the iconic sunburst chairs while taking in the beautiful view of Lake Mendota.” 

Cycle around the bike-friendly city 

Local photographer Sharon Vanorny states, “Madison is a magical city! My favorite thing to do in the summer in Madison is to rent a B-Cyle bike and go down State Street. Stop at the Memorial Union to see the chairs and water.” Renting a bicycle is an incredible idea when visiting as Madison has a reputation as one of the most bike-friendly cities in the nation. As a bicycle-friendly community, the city offers over 200 miles of biking and hiking trails, a perfect addition to any outdoorsy person’s Madison bucket list. Exploring the city on two wheels is not only effortless but also incredibly scenic. Another local, Nikki Johnson from The Tacky Tourist supports this idea and comments, “I love walking or renting e-bikes to enjoy our beautiful trails! Some of my favorites are the Lower Yahara River Trail, Capital City Trail, Starkweather Creek Path, and the Lakeshore Path,” 

Lush greens at the botanical gardens

Immerse yourself in the beauty of Olbrich Botanical Gardens, where rich landscapes, fragrant flowers, and serene water features create the perfect setting. The garden hosts 16 acres of outdoor gardens and the Bolz Conservatory houses more than 650 plants. The Olbrich Botanical Gardens also hosts a variety of classes and events suitable for all ages, covering topics ranging from arts and wellness to learning and beyond. 

We talked to a local, Tammy Schreiter from Hatch Art House who suggests, “recommending visitors start their day wandering around at Olbrich Botanical Gardens. Afterward, head over to the Willy Street neighborhood and grab lunch at Mickey’s Tavern on their beautiful back patio. Since you are on Willy Street, walk off your lunch while checking all the great shops along the way including Hatch Art House and Hazel General Store!” 

Discover Willy Street 

“I would recommend that new residents spend a day exploring the Williamson-Marquette (AKA Willy Street) and Atwood historical neighborhoods. A short walk or bike ride in any direction will take you to cool local restaurants, shops, and parks, with Olbrich Botanical Gardens and Biergarten looking over Lake Monona at the far end of it” says Paulius Musteikis, a Madison photographer.

The Williamson-Marquette is an older Madison neighborhood with a vibrant vibe located in the heart of Madison. Lined with colorful storefronts, cafes, and trendy boutiques, Willy Street attracts residents and visitors alike. Willy Street embodies the progressive spirit of Madison, offering a warm welcome to all who wander its lively streets.

Wander through museums

Delve into the world of art at the Chazen Museum of Art, home to an impressive collection of approximately 25,000 works of art. Art from ancient Greece, 18th-century Japan, Africa, and more can be found in this collection that pans diverse cultures and time periods. Just walking distance away from the State Capitol and with free admission, it is an accessible cultural experience for all.

Another popular stop is the Madison Museum of Contemporary Art (MMOCA). Maureen Cassidy, a local photographer, suggests visitors stop by and, “immerse yourself in inspiring fine art at the Madison Museum of Contemporary Art (MMOCA). Located in the heart of downtown Madison, Wisconsin, this cultural hub showcases an eclectic array of thought-provoking exhibitions and avant-garde installations from emerging and established artists. Explore the museum’s diverse collection spanning various mediums, from painting and sculpture to photography (my favorite!) and new media. Take advantage of enjoying the picturesque rooftop!”

Local flavors, fresh finds, farmers markets

“Any new resident to Madison will quickly discover they’ve landed in a city full of farmers markets,” says Benjamin Zimmerman from Westside Community Market. “From the iconic Dane County Farmers Market, held weekly around the state capitol, to the neighborhood markets held throughout the city, there’s hardly a day of the week in the summer without the chance to buy the best in fresh produce, locally raised meats, yummy Wisconsin cheeses and more.” 

Kathryn from Capitol View Farmers’ Market supports this recommendation by suggesting to visitors, “Enjoy great local vendors, food carts, live music, activities for kids, and more! It’s a quintessential way to spend a summer-fall afternoon on the east side of Madison.”

Garver Feed Mill, all in one stop 

When exploring Madison’s vibrant east side, make sure to prioritize a visit to Garver Feed Mill next to Olbrich Botanical Gardens. It’s a local gem brimming with experiences to savor,” says Bryant Moroder from Garver Feed Mill. “Start your day right by perusing the Saturday farmers market in winter, indulging in fresh produce, Wisconsin cheese, and homemade baked goods. Stay entertained with live music performances or unwind with games and a refreshing bubble tea at Roll Play. And for the ultimate relaxation, treat yourself to a spa service at Kosa, where you can rejuvenate amidst the historic charm of the mill.”

Take a glimpse into democracy

The tallest building in Madison, the Wisconsin State Capitol houses the chambers of the Wisconsin legislature, the Wisconsin Supreme Court, and the Office of the Governor. Open daily to the public with free tours available, the Wisconsin State Capitol is a must-visit. Visitors can experience a beautiful view of Madison on the sixth-floor observation deck. The Capitol encourages people to stop by and explore around the area. On Saturday and Wednesday mornings from April through November, visitors can visit the Dane County Farmers Market, the country’s largest producer-only farmer’s market at Capitol Square. 

Savor the flavor of Madison

“After a long day exploring the Wisconsin State Capitol and State Street, you’ll definitely want to grab food downtown,” says Valerie Halling a local photographer. “With Madison being a foodie city, there are endless restaurants to choose from, but for an extra special dinner, check out Eno Vino Downtown! It’s a modern, luxe restaurant perched on the 10th floor of the AC Hotel with arguably the best rooftop view of the Capitol building.” 

John Mleziva from State Line Distillery also suggests “There are a few ‘must check out’ places and activities that I would recommend. For an amazing meal with stunning views check out Sardine. Their food and cocktails are top-notch and never disappoint. If you are looking for an intimate spot to sip on a cold beverage from an expertly curated beer list, head to The Mason – one of the best-kept secrets in town. Lastly, for a quintessential Madison experience, pack a picnic basket, a bottle of wine, and head down to Concerts on the Square.

Revel in aquatic adventures

“A perfect Saturday in Madison consists of lounging at the Memorial Union Terrace, sharing a pitcher of beer with friends, and enjoying Wisconsin’s finest ice cream while watching the sailboats on Lake Mendota,” comments Courtney Terry, a local Madison photographer. However, some wish to experience the Madison lakes firsthand. Climb aboard on a scenic boat tour voyaging Lake Mendota, and enjoy breathtaking views of the city skyline, pristine shorelines, and historic landmarks as you glide across the shimmering waters.

Photographer Catherine Hilcove shares an alternative option, “One of my family’s favorite warm-weather activities is a trip to Lake Wingra for boating or paddleboarding and a picnic. You can bring your own paddleboard, kayak, or canoe or rent one from Wingra Boats. Bring your picnic blanket and some food (or purchase something yummy from one of the surrounding restaurants) and enjoy an afternoon by the water.” 

Ansley McLeod from Ansley’s Art also suggests, “A must-do for any new Madison resident is kayaking on our beautiful lakes! Specifically, you’ll want to rent kayaks at Brittingham Boats and paddle onto Lake Monona for a breathtaking view of your new city.” So whether you are taking a guided tour, kayaking, or swimming in the lakes, Madison’s beautiful lakes offer a refreshing stop to cool off.

More farmers markets to visit

We weren’t kidding when we said Madison is full of farmers markets. Farmers markets can be found in different locations giving people shopping convenience. Amber from Monroe Street Farmers Market suggests stopping by the Monroe Street Farmers Market open May-October on Sundays from 9 am-1 pm. Monroe says, “From crisp vegetables to artisanal cheeses, from handmade crafts to unique local delicacies, the market offers a treasure trove of goods that you won’t find anywhere else. The Monroe Street Farmers Market isn’t just about shopping—it’s about community. Run by a dedicated group of market vendors and neighbors, the market aims to create a welcoming space where neighbors can come together to connect, chat, and enjoy each other’s company. And let’s not forget about the entertainment! As you peruse the stalls and fill your bags with goodies, you’ll be serenaded by local musicians adding a soundtrack to your shopping experience. We have kids’ activities and other fun events throughout the summer. It’s the perfect backdrop for a stroll through the market aisles.”

Live musical performances

No matter your location in Madison, live music will seek you out, enriching your life with an exciting soundtrack. Join locals and visitors alike for a laid-back evening of live music on the Memorial Union Terrace, or local spots including Mickey’s, Crystal Corner, and High Noon. Every June 21st Make Music Madison celebrates with music festivals. Kristian Iliev from Make Music Madison explains, “Make Music Madison is the local chapter organizing for Make Music Day, which reminds us how valuable music is and also recognizes the summer solstice. Last year, over 600 events filled the city with music, more than any Make Music chapter in North America! Plan for this year by discovering the performers and venues with officially registered events at: makemusicmadison.org/listings” 

A City of Art 

“Madison has a lot of ways to enjoy the arts for free,” expresses Gretchen Olson from Crimson Artist Collective. “Whether you attend Wisconsin Chamber Orchestra’s free outdoor concerts on the square in the summertime, the new exhibit at the Madison Museum of Contemporary Art, or an evening of dancing at one of the Dane Dances, there is something for everyone.” As Olson expressed there is an abundance of art to enjoy including murals across the city. Jillian Talarczyk, the Founder & Creative Director of the Madison Public Art Project suggests, “doing a public art tour of the exciting murals the city has to offer! For a great bucket list biking or walking itinerary start by visiting the Flamingo Swirls mural at 701 East Johnson Street. Continue into the Arts & Mural district of Monona to view the Riding Waves mural at Hwy 12/18 at the Monona Dr. underpass exit. Once in Monona, make sure to visit the 15 painted Vibrant Hydrants along Monona Drive.”

Whether you’re seeking a cultural experience, outdoor exploration, or simply a taste of local flavor, Madison offers unforgettable experiences. So pack your bags and hit the road, an adventure in Wisconsin’s vibrant capital city awaits you.

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