A Perfect Fall Weekend in Madison: What to Do, Where to Eat and Where to Stay

An ideal weekend destination is best kept to no more than three hours away. Close your computer at 4 p.m. and arrive just in time for Friday-night festivities. Only 122 miles from Chicago, Madison, Wis., clocks in at just over two hours from the North Shore. 

With a small-town vibe and big-city perks, it won’t take much badgering to persuade your crew to head to the City of Four Lakes. Nestled between Lake Monona and Lake Mendota, Madison is one of two major U.S. cities (Seattle is the other) built on an isthmus. 

Walk around UW-Madison to take in the fall colors. Photo by Focal Flame Photography/Courtesy of Destination Madison. 

Madison is home to the University of Wisconsin-Madison, but you don’t have to be a college student to love Mad City. There’s something for everyone — from foodie bike tours and Ayurvedic spa experiences to jazz nights and vintage shopping. Here’s what to do, where to eat and what you should know before booking a fall getaway to Madison.

What to do 

Garver Feed Mill

Located in a rehabbed, turn-of-the-century building, Garver Feed Mill offers a rich Madison experience all under one roof. A dozen locally owned businesses now operate out of Garver Feed Mill including Ledger Coffee Roasters, Perennial Yoga, Nessalla Kombucha and Sitka Salmon Shares. On Friday night, you can enjoy a cocktail at Garver Lounge while listening to avant-garde jazz. Saturday morning, head right back for brunch. 

Garver began as a sugar beet processing facility in 1906 and later served as a factory for formulating livestock feed. In the two decades it sat vacant, graffiti artists used the deteriorating building as a canvas. Restoration of the Feed Mill began in 2017, and the transformed space officially reopened in 2019. Baum Revision, a Chicago-based real estate development company, took care to preserve historic markers of the building’s many lives: the original 60-ft. steel trusses, 90 historic windows and even a graffitied shark person on exposed brick. 

Sip on a craft cocktail at Garver Lounge. Photo Courtesy of Baum Revision.

“Garver Feed Mill has been recognized as one of the area’s top destinations and hotspots for wellness, and we are looking forward to introducing this magical place to our Chicago-area neighbors looking for an easy and welcoming getaway,” says Bryant Moroder, a member of the development team.

If you’re not much of a planner, let Garver take the reigns. They offer curated foodie, wellness and art experiences

Heads up, Chicago Brides: The Feed Mill has all of the architectural details you’ve saved on Pinterest. Lucky you, Garver Events hosts weddings and receptions. They also partner with on-site vendors, like boutique flower studio Briar Loft, to make your day easy and dreamy. 

KOSA Ayurvedic Spa & Retreat 

Stash your phone in a locker and retreat into the meditative atmosphere of KOSA. When Shilpa Sankaran saw Garver Feed Mill come to life, she knew the building would be the ideal spot to pursue her lifelong dream of opening a wellness spa. KOSA offers a nurturing environment with authentic Ayurvedic spa experiences. Ayurveda, an Indian art of medicine dating back over 5,000 years, is based on the principle that all elements of nature are a part of us, and we have a higher quality of life when they are balanced. 

Kosa Spa’s quiet sanctuary. Photo Courtesy of Baum Revision.

Through custom body treatments like an organic Inner Glow Facial or Abhyanga, a warm oil massage, practitioners help guests find that balance. During your retreat, you may reflect in the quiet sanctuary or spend time in the sauna and steam room. Enjoy a cup of tea while you relax, or try one of KOSA Kitchen’s healing Indian dishes.

Bike n’ Bites Food Tour

Going to Madison without getting on a bike is like going to Chicago and not taking the Architecture Tour. It’s one of only five cities to receive a “Platinum Bicycle Friendly Community” rating from the League of American Bicyclists, and there are more than 200 miles of paths for biking and hiking.

Rent a Madison BCycle at Garver Feed Mill. Photo Courtesy of Baum Revision.

Biking isn’t for everyone, but you might change your mind when you try a Madison BCycle electric bike. Just like the Divvy bikes in Chicago, BCycles are a fun and affordable way to get around town. The electric bikes make riding easy by giving you an assist. That means you can ride for miles and uphill without breaking a sweat. 

Madison Eats Food Tours will take you on a guided BCycle food adventure through the Willy Street, Atwood and Olbrich neighborhoods. Seven tastings, two drinks, six miles roundtrip. Eat, ride, repeat. And that brings us to…

Where to eat

Ian’s Pizza 

Ian’s famous mac n’ cheese pizza. Photo Courtesy of Baum Revision.

All you need to know is Mac n’ Cheese pizza. Carbs on carbs. The perfect food for munchies. Ian’s Pizza began in Madison with the mission to sell affordable, craft-quality pizza. You can get a massive slice of the Mac or any other specialty slice for under $5. And thank goodness it’s affordable because you’ll keep going back for more. The Macho Nacho and Drunken Ravioli pizzas will take pizza connoisseurs to the next level. The best part? They put people first, supporting their employees and encouraging entrepreneurship. They’ve grown to eight locations, three in Madison, with many of the business owners starting as Ian’s employees. 

Monsoon Siam

Bike n’ Bites Food Tour stops at Monsoon Siam. Photo by Caroline Hetzel.

When dining out wasn’t an option, Monsoon Siam became the go-to take-out spot for many Madisonians. The no-frills neighborhood cafe serves seasonally inspired Thai cuisine with a commitment to using local and sustainable ingredients. If you want to stick with familiar Thai dishes, you can’t go wrong with Drunken Noodles or Pad Thai. Want to try something new? Order the Kapow Moo Krob—crispy pork belly stir fried with string beans, onions, chili, pepper and basil served in a spicy basil sauce. If you’re on the Madison Eats Tour, you might get to try some items off the secret menu. 

Chocolate Shoppe Ice Cream Company

Zanzibar chocolate cone at Chocolate Shoppe Ice Cream Company. Photo by Caroline Hetzel.

Another Madison institution, the Chocolate Shoppe Ice Cream Company will convince you that all ice cream should be made from Wisconsin dairy. Chuck Sr. and Nancy Deadman opened the ice cream shop in 1962 to bring sweet happiness to their community. Now a second-generation company, the Chocolate Shoppe produces more than 100 “super-premium” ice cream flavors. This fall, keep your eyes open for their seasonal pumpkin scoop. The smooth, spiced pumpkin ice cream flavored with pumpkin puree tastes just like autumn. 

Short Stack Eatery

Breakfast sandwich on a spicy cheese roll at Short Stack Eatery. Photo by Caroline Hetzel.

Breakfast lovers, rejoice! This female-owned restaurant in Downtown Madison serves breakfast — and only breakfast — all day. Who needs lunch anyway? Especially when you can have a breakfast sandwich that would impress Ron Swanson. The community-minded joint is committed to fighting racial injustice and inequity. They’re working toward a healthy Madison for all by supporting Wisconsin farmers and small-batch suppliers, offering discounts to bikers and partnering with several nonprofits. Walking inside Short Stack is easy. Choosing what to eat is hard. And that’s OK because you can order the Blind Special. All you need to do is tell them if you want a sweet or savory dish, and they’ll bring you one of their best items on the menu. The pecan streusel French toast made with a sourdough baguette and topped with maple bourbon mascarpone and caramel is also a good choice, but you may need a nap afterwards. 

Dotty Dumpling’s Dowry

Truffle fries at Dotty Dumpling’s Dowry. Photo by Caroline Hetzel.

No visit to America’s Dairyland is complete without an order of cheese curds. Dotty Dumpling’s Dowry — say that three times fast — serves theirs with housemade ranch and honey mustard sauce. A favorite among locals, this burger-slinging classic arrived in Madison in 1974. The best selling Melting Pot burger piles on the cheese: cheddar, swiss and provolone with smoked bacon and their signature English Garlic Sauce. (Shilpa Sankaran of KOSA Spa recommended this spot. It’s all about balance!)

Where to stay

Hotel Indigo Madison Downtown

Hotel Indigo occupies the historic Mautz Paint Company building. Photo by Caroline Hetzel.

Just a short walk from Capitol Square, Hotel Indigo in Madison Downtown recently opened in the landmark Mautz Paint Company building. A large portion of the hotel occupies the century-old paint factory, and creative murals and decor pay homage to its colorful roots. In the newly built addition, Palette Bar & Grill serves American eats that don’t disappoint. They also welcome pets of all shapes and sizes, so you can explore dog-friendly Madtown with your best friend. 

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Caroline Hetzel lives in the Uptown neighborhood of Chicago with her fiancé and two dogs. She’s a Tennessee native who likes local breweries, DIY projects, and vintage Pyrex. After graduating from Northwestern University, she spent three years in the San Francisco Bay Area creating videos and content for Brit + Co and Sunset. Caroline loves dogs and has volunteered at PAWS Chicago and supports Second City Canine Rescue, where she adopted her second dog Foggy. 

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