Pedal, Paddle and Pour: Savoring Madison, Wisconsin’s Cuisine, Comedy and Community

Madison, Wisconsin is ensconced between the sparkling waters of two magnificent lakes which creates an isthmus, one of only two large cities in the U.S. that can lay claim to this interesting phenomenon. Madison effortlessly blends urban sophistication with the tranquil embrace of nature. A city that thrives on diversity, culture, and innovation, and a spirit infused into its every corner of its community, making it an irresistible destination for visitors. From its iconic landmarks, such as the magnificent Capitol building, to the bustling energy of its downtown streets, Madison boasts a kaleidoscope of experiences, from culinary wonders to dynamic community engagement. Madison is a place where every step brings you closer to a tapestry of excitement waiting to be unraveled.

Madison Wisconsin Capitol building aerial photo by

I spent just three days in Madison, but wasted no time taking in as much as I could. I will share with you the highlights (and recommendations) of my long mid-July weekend, which I think will make for a perfect itinerary should you decide to visit this vibrant Midwestern capital city.

Sipping in Scenic Splendor at Wollersheim Winery & Distillery

Just days earlier I had been in Eau Claire, Wisconsin for a TBEX travel conference, so I road tripped to Madison (about 185 miles to the southeast) with some fellow travel bloggers. Along the way, about 30 minutes outside of Madison, we stopped at Wollersheim Winery & Distillery for some tastings and lunch.

Wollersheim Winery & Distillery

As we stepped into the rustic charm of the vineyard, I felt an immediate sense of tranquility. The winery’s picturesque location, nestled amid rolling hills and lush vineyards, was a sight to behold. Eager to indulge in their offerings, we made our way to the spirit room. While they have a few offerings, i.e. brandy, gin and rye, the true highlight for me was the bourbon, where the complex flavors and intricate notes danced on my palate. After our spirit tasting, we made my way to the terraced patio overlooking the vineyards for a leisurely lunch and wine tasting. The picturesque view was a perfect accompaniment to the delectable farm-to-table cuisine, where fresh, local ingredients elevated every dish to new heights. Basking in the warm sun and savoring the delicious flavors, I couldn’t help but feel grateful for the extraordinary start to our Madison adventures.

A Journey Through Time, Tradition, and Taste at J. Henry & Sons

As we continued toward Madison, we stopped at J. Henry & Sons for a tasting of their acclaimed bourbons. Located on a farm that has been in the family for over five generations, J. Henry is not just a distillery – it’s a testament to a deep-rooted love for the land and its yield.

J. Henry & Sons Bourbon farm - photo by

We were welcomed by Jaydon, whose passion for bourbon was palpable. We learned that the bourbon was crafted using heirloom red corn, wheat, and rye, all grown on their own farm, capturing the essence of Wisconsin’s rich agricultural heritage in every bottle.

The tasting room, adorned with rustic charm, was filled with an array of bourbon bottles, each offering a unique flavor profile. Jaydon walked us through each sample, explaining the nuances that set J. Henry & Sons apart. From their signature five-year-old bourbon, filled with notes of caramel, vanilla, and a touch of cinnamon, to their Patton Road Reserve, a single barrel proof expression, the tasting experience was an education in craftsmanship and flavor.

After the tasting, we were taken on a tour of the grounds and rickhouses, where the bourbon is aged. Seeing rows upon rows of barrels, each slowly maturing over time was captivating. The aging process at J. Henry & Sons is unique – they utilize Wisconsin’s varied seasons, which swing from hot summers to freezing winters, to deepen their bourbon’s complexity and character. Our visit was more than just a tasting; it was a journey through time, tradition, and taste. It’s a stop I highly recommend for anyone with an appreciation for finely crafted spirits.

A Comfortable Respite: Checking into The Madison Concourse Hotel

After a day of tastings and tours, we arrived at our accommodations for the rest of the trip – The Madison Concourse Hotel. Located in the heart of downtown Madison, just a stone’s throw away from the stunning Capitol building, the hotel is perfectly situated for exploring the city by bike or foot.

The Madison Concourse Hotel offers a blend of comfort, convenience, and a hint of luxury that perfectly encapsulates the Madison experience. With its modern and spacious rooms, you can enjoy views of the city’s skyline, providing a beautiful backdrop as you unwind from the day’s activities.

Noteworthy within the hotel is the Governor’s Club Lounge. Offering views of the city and the Capitol, this exclusive retreat is perfect for enjoying an evening with fellow travelers while sipping on a cocktail.

Brittingham Boats: An Unforgettable Lake Adventure in Madison

As the sun began to cast long shadows across the sparkling waters of Lake Monona, we found ourselves at Brittingham Boats, ready to embark on a unique water-bound adventure. This wasn’t your typical kayak rental experience; Brittingham Boats offers an evening full of fun, music and food – all while on the water.

The renting process was seamless, and before we knew it, we were in our kayaks, paddling through the calm waters. The lake was a busy but harmonious scene, with kayaks, paddle boards, and boats bobbing on the gentle waters.

Chris Mitchell with Traveling Mitch having a burger while kayaking in Madison

In the middle of it all was a lively barge filled with musicians playing a mix of hits, their energetic tunes providing a perfect soundtrack to the evening. The live music echoed across the lake, setting a tone of jovial community spirit that made our paddling experience all the more enjoyable.

And if that wasn’t enough, the tantalizing aroma of grilling burgers wafted across the water. Another barge, loaded with a grill was cooking up juicy burgers. The combination of food, music and the beautiful setting created an atmosphere that was electric, turning a simple kayak trip into a celebration on water.

Evening Stroll: Soaking in Madison’s Architectural Marvel

Leaving behind the revelry at Brittingham Boats, we began to walk back to our hotel. The route took us along the shore of another of Madison’s beautiful lakes, offering a tranquil backdrop for the evening stroll. The sun was setting, casting a golden hue across the water and painting the sky in shades of orange and pink. It was a perfect time to reflect on the day’s adventures and look forward to what Madison still had to offer.

One of the highlights of our walk was passing by the Monona Terrace Community and Convention Center. This architectural marvel was designed by none other than Madison’s own, Frank Lloyd Wright. Wright’s distinctive style, characterized by harmony between human habitation and the natural world, was on full display. The building’s organic curves and sweeping lines echoed the surrounding landscape, seamlessly blending with the lakeside setting.

Monona Terrace Community and Convention Center

I took a moment to admire this testament to Wright’s genius, its silhouette illuminated against the fading evening sky. The convention center, much like Madison itself, seemed to blend the natural and the man-made in a beautiful symbiosis. Our stroll back to the hotel was not just a journey through the city’s streets, but a walk through Madison’s rich cultural and architectural history.

As we neared the hotel we could hear music playing in the distance, come to find out they had a street blocked off near the capitol building with a large stage and a popular local band performing. This was an outstanding ending to our action-packed first day in Madison, Wisconsin.

Morning Awakening: Madison’s Spectacular Farmers’ Market

Awakening to the dawn of a new day, I stepped outside the Madison Concourse Hotel, ready for another day of exploration. The city was already abuzz with activity, as vendors set up for the famed Dane County Farmers’ Market that wrapped around the massive Capitol building (Wednesday and Saturday).

As I strolled through the market, I was struck by its sheer scale and the dizzying array of fresh produce on display. From vibrant fruits and vegetables to artisanal cheeses and bread, homemade jams, and beautiful bouquets of flowers, the bounty of Wisconsin’s farmland was in full force. But what truly sets Madison’s Farmers’ Market apart is its community-driven spirit.

Each stall was manned by the very farmers and craftsmen who had produced these goods, eager to share their stories and passion for their products. As a matter of fact, the market adheres to a “producer-only” rule, ensuring that everything sold is grown or crafted by the seller. This commitment to local products not only supports the local economy but also guarantees an unrivaled freshness and quality.

A Culinary Rendezvous: Brunch at Graze

As the morning unfolded, I found myself at Graze, an iconic farm-to-table restaurant for a hearty brunch. I met up with my fellow travel bloggers, and the anticipation of a shared meal in good company added a zest to the morning’s excitement.

Graze is run by James Beard Award-winning chef Tory Miller, who brings his commitment to local, sustainable ingredients to every dish. The menu was an enticing showcase of Wisconsin’s finest produce, re-imagined through Chef Miller’s innovative culinary lens.

Crave restaurant in Madison Wisconsin - Photo by Mike Shubic of

The atmosphere inside Graze is light and welcoming, the decor reflecting its farm-to-table ethos with an elegant touch. The buzz of conversation filled the air, coupled with the enticing aroma of freshly cooked food.

As we gathered around the table, sharing travel stories and our experiences in Madison thus far, we delved into a gastronomic feast. From savory benedicts to sweet pancakes, each dish was a celebration of flavor and freshness. As we left Graze, our bellies full and spirits high, we were ready for more Madison adventures.

Exploring Madison’s Cultural Canvas: A Journey through Art and History

After brunch, we decided to disperse and explore Madison individually. With its vibrant cultural scene and numerous museums, there was no shortage of attractions to keep me engaged. My first stop was the Madison Museum of Contemporary Art.

Madison Museum of Contemporary Art

The museum, free to the public, offers a dynamic roster of exhibitions and educational programs. As I walked through the galleries, I marveled at the creativity and boldness of the contemporary pieces on display. From large installations to intricate paintings, the museum was a testament to Madison’s thriving artistic community and its appreciation for contemporary art.

Next, I headed to the Wisconsin Historical Museum, where the state’s rich history came alive through compelling exhibits and artifacts. The museum does an excellent job of telling the story of Wisconsin’s past, from its Native American roots to its growth into the diverse, innovative state it is today. Despite the complexity of the history, the museum presents it in an engaging and accessible way, making it a must-visit for anyone interested in Wisconsin’s past.

New Orpheum in Madison, WI - Photo by: Mike Shubic of

One of the things I appreciated most about Madison was its commitment to making cultural and educational attractions accessible to everyone. Many of the city’s museums, including the ones I visited, offer free entry, opening the door for everyone to explore and learn. This sense of inclusivity is a testament to Madison’s community spirit and its dedication to celebrating its rich history and vibrant arts scene. As I concluded my museum visits, I was left with a profound appreciation for Madison’s depth and diversity.

Stroll Down State Street: The Journey to Memorial Union

My day of exploration continued as I made my way down State Street, a vibrant thoroughfare that links the Wisconsin State Capitol and the University of Wisconsin-Madison campus. Lined with an eclectic mix of shops, galleries, restaurants, and cafes, State Street offers a slice of Madison’s lively spirit.

Memorial Union - Photo by: Mike Shubic of

As I ambled along the bustling street, I took in the sights and sounds of this energetic avenue. Street performers filled the air with music, while colorful murals and installations added an artistic flair to the urban landscape. As State Street segued into the university campus, I was greeted with lush green spaces and picturesque paths winding through the grounds, embodying the campus’s welcoming and inspiring atmosphere.

My journey concluded at the Memorial Union, an iconic Madison landmark perched on the shores of Lake Mendota. Here, I sat down for a leisurely lunch, the Union’s outdoor terrace providing a stunning view of the shimmering lake. There was a palpable sense of camaraderie, as students, locals, and tourists alike relished the union’s convivial atmosphere. The sound of laughter mingled with the lapping of the lake waves, creating a perfect soundtrack for my meal.

A Madison Institution: Cocktails and Conversations at The Old Fashioned

As the afternoon sun began to wane, my travel companions and I regrouped at a local favorite watering hole: The Old Fashioned. Situated in the heart of downtown, this Madison institution is known for its unique spin on Wisconsin’s namesake cocktail.

Our order of Old Fashioned cocktails arrived, their caramel hue glowing against the backdrop of the rustic bar. What set these drinks apart is The Old Fashioned’s distinctive twist, a secret blend that elevates the classic to a new level.

Lazy Susan appetizer - A Wisconsin Tradition at the Old Fashion

As we sipped on our cocktails, we also ordered a Wisconsin tradition that epitomized the state’s love for hearty, communal meals – the Lazy Susan. A smorgasbord of local delights, it featured an array of shareable treats including Salami, Bavaria Kitchen’s Braunschweiger, smoked trout, creamed herring, Dusseldorf mustard, pickles, and deviled eggs. It was all served alongside Widmer’s Brick & Vern’s Sharp Cheddar spread with a side of crackers & rye, creating a symphony of flavors that brought together the best of Wisconsin’s culinary offerings.

Upscale Dining: A Delightful Evening at Heritage Tavern

As the evening descended upon Madison, we found ourselves at the doorstep of the Heritage Tavern, ready for a fine dining experience. Renowned for its upscale farm-to-table fare, Heritage Tavern has been a culinary cornerstone in Madison for its creative menu that highlights the best of Wisconsin’s produce.

Stepping into the Heritage Tavern, we were greeted by a classic, intimate atmosphere. Our meal was a gastronomic journey through Wisconsin’s finest produce, expertly prepared to showcase the ingredients’ inherent flavors. From succulent meats to fresh, vibrant vegetables, every dish was a testament to the skill and creativity of the kitchen. Each course unfolded like a story, presenting a unique blend of textures and flavors that danced on the palate.

Meal at Heritage Tavern

But more than just the incredible food, it was the overall dining experience that made our evening at the Heritage Tavern so memorable. The attentive service, the ambient lighting reflecting off the vintage fixtures, the hum of quiet conversation – it all contributed to the feeling of elegance and warmth that defines this Madison gem.

A Night of Laughter: Unforgettable Moments at the Comedy Club on State

Our evening of gastronomical delights was followed by an equally delightful indulgence of the humorous kind. We headed to the Comedy Club on State, a vibrant hub of Madison’s nightlife that regularly hosts a cavalcade of comedic talents. On this particular night, the headlining act was none other than Kevin Bozeman.

From the moment he stepped on stage, Bozeman had the audience doubled over in laughter. His witty quips, incisive observations, and relatable anecdotes created an electrifying energy that echoed throughout the room. His comedic style, sharp yet light-hearted, was infectious, turning the entire room into a sea of laughing faces.

Kevin Bozeman on stage at the Comedy Club on State in Madison, WI

But it wasn’t just Bozeman who kept the humor quotient high. From the emcee to the warm-up act, everyone was sensationally funny. It was as if laughter was the shared language for the evening, uniting everyone in the room in a shared experience of joy and amusement.

Rise and Shine: A Morning Feast at the Short Stack Eatery

With the taste of laughter still fresh from the night before, the morning beckoned us to a different kind of experience. We found ourselves at the Short Stack Eatery, a local Madison favorite that’s dedicated its menu to the most important meal of the day – breakfast.

Stepping into the Short Stack Eatery, we were instantly welcomed by the delightful aroma of freshly brewed coffee and the tantalizing scent of sizzling breakfast staples. The lively atmosphere, with its bustling energy and warm lighting, was the perfect setting to shake off the morning grogginess and start the day on a high note.

Pancakes at Short Stack Eatery

The menu at the Short Stack is a treasure trove of breakfast delights. From fluffy pancakes to hearty egg dishes, every option was an homage to the joy of a good breakfast. Each dish was crafted with care, utilizing fresh ingredients to create a breakfast experience that was both comforting and satisfying.

Riding High: Exploring Madison on an E-Bike Tour with Madison Adventure Tours

Fueled by a delicious breakfast, we were eager to further explore Madison and opted for an e-bike tour. Our adventure was guided by Madison Adventure Tours, a local company known for their engaging and informative tours. Garret, the owner himself, donned the hat of our guide, infusing the journey with his infectious enthusiasm and extensive knowledge about the city.

Madison Adventure e-bike tour

The e-bike tour was a whirlwind of sights and sounds, taking us through the city’s vibrant neighborhoods, past iconic landmarks, and along the breathtaking shores of Lake Mendota, Lake Monona, and Lake Wingra. The joy of the e-bikes was the freedom they offered, allowing us to cover large distances effortlessly, leaving more room for enjoyment and exploration.

A Culinary Journey: Downtown Madison Food Tour with Madison Eats

From e-bikes to food bites, our Madison exploration continued with a delectable food tour of downtown Madison’s Capitol Square and its environs with Madison Eats. This tour was a veritable feast of classic Wisconsin fare, allowing us to experience the “real Wisconsin” flavors while uncovering hidden culinary gems scattered throughout the city.

Over the course of the tour, we made five generous stops, each offering a unique taste of Madison’s culinary scene. The highlight for me was probably Lucille for both its wonderful atmosphere and tasty food. An insider’s tour of the Capitol building was also included, giving us a dose of history and culture amid our culinary explorations.

Lucille restaurant and bar in Madison

Finally, we ended our food tour on a sweet note, indulging in real Wisconsin ice cream. The creamy, delicious dessert was the perfect end to our gourmet journey, leaving us with a lingering taste of Madison’s culinary brilliance.

Farewell Madison: A Parting Glance from the Dane County Regional Airport

As my Madison adventure came to a close, I was whisked away by the hotel’s transport to the Dane County Regional Airport, just a mere 10-minute ride away. Despite its status as a capital city airport, Dane County Regional is refreshingly small, adding to the charm of Madison’s down-to-earth vibe.

Stepping into the airport, I was pleasantly surprised by how easy it was to navigate. The compact size, clear signage, and friendly staff ensured a smooth transition from the check-in counters to the boarding gates. The airport might lack the grandeur of its counterparts in larger cities, but it made up for it with its efficiency and ease of use.

As I sat at the gate, waiting for my flight, I found myself reminiscing about my Madison adventure. From the rolling vineyards of Wollersheim Winery to the vibrant neighborhoods explored on e-bikes, from the rich flavors of the food tour to the hearty laughter at the Comedy Club on State, every experience was a slice of Madison’s vibrant spirit.

Madison Wisconsin Aerial photo by Mike Shubic of

Looking out of the window, watching the city shrink as the plane took off, I felt a sense of contentment. Madison, with its blend of urban energy, natural beauty, culinary wonders, and community spirit, had offered me a unique and unforgettable adventure. As the cityscape faded into the distance, I knew one thing for sure – this was not a goodbye, but a see-you-later to Madison, Wisconsin.

If you have any questions about visiting Madison, Wisconsin, or would like to share your favorite parts of this city, leave a comment below. So, until next time, we’ll see ya on the road…

Mike Shubic

Mike Shubic is a seasoned road trip travel video blogger, traversing the byways of the world looking for those hidden gems of the road. From unique destinations, unexpected discoveries, creative cuisine, intriguing inns to exciting attractions…the road is his page. The experiences are his ink. And every 300 miles, a new chapter begins. Whether you live vicariously or by example, Mike will do the exploring so you can have an adventure.