Drink Your Way Through Cheese Country: Discovering the cheese and liquor trends of Wisconsin by train (Itinerary)

Travel across Wisconsin on the Empire Builder train with stops in Milwaukee, Wisconsin Dells, and La Crosse to discover the best places for a craft brew or distilled spirits — and, of course, plenty of cheese.

Day 1 – Milwaukee

Welcome to Milwaukee!

Located on the “Fresh Coast” of Lake Michigan in southeastern Wisconsin, Milwaukee is recognized for its outstanding performing arts groups, professional sports teams, and nationally acclaimed zoo, as well as its art and natural history museums. Among the city’s gems are Discovery World at Pier Wisconsin, Miller Park stadium, the Harley-Davidson Museum, Milwaukee Public Museum, and the iconic Milwaukee Art Museum, which has garnered international acclaim. Also known as the “City of Festivals,” Milwaukee offers top-notch ethnic and music festivals year-round, beautiful botanical gardens, unique architecture, expansive parks, and diverse shopping opportunities. Milwaukee is home to restaurant after delicious restaurant, from traditional German spots and classic steakhouses to cutting-edge farm-to-table eateries. 

Check in at DoubleTree by Hilton Hotel Milwaukee Downtown

Pabst Brewery / Facebook

Tour Best Place at the Historic Pabst Brewery

After the Pabst Brewery closed in Milwaukee in December 1996, it sat empty until 2001. It was at that time that Jim Haertel received his accepted offer to purchase the Pabst Brewery on September 11, 2001. Great care has been taken to ensure that Blue Ribbon Hall, The Great Hall, Captain’s Corner, Captain’s Courtyard, Guest Center, King’s Courtyard, and the original Gift Shop have all been restored to their original glory. Since the first phone call was placed inquiring about buying the property, the brewery is once again full of life and laughter as “Best Place at the Historic Pabst Brewery” and is once again open and ready to welcome you.

Milwaukee Brewing Company / Facebook

Tasting at Milwaukee Brewing Company

Voted as Milwaukee’s Best Craft Brewery of 2019, Milwaukee Brewing Company (MKE) has come a long way since opening in 1997. By staying true to its foundational roots, MKE has created a sustainable, creative, and innovative brewing environment unlike any other. Paired with the opening of MKE 9th St., a destination brewery and taproom located just outside the Deer District, the brewery is paving the way to becoming a household name throughout the Midwest.

MKE 9th St. is a culmination of 5 years of effort in design and innovation from the MKE team. Featuring a state-of-the-art brew system, the brewery combines the latest technology and unique capabilities for creative expression in adult beverages. Technology at the brewery is being used for energy efficiency, consistency in the brewing process, safety, and a waterfall of data to continuously improve quality.

Central Standard Distillery / Facebook

Dinner and tasting at Central Standard Distillery

A better craft spirit experience awaits. Our award-winning products are locally distilled with pride, right in the heart of Downtown Milwaukee. And now, experience our full offering with the Central Standard Crafthouse & Kitchen. Cocktails, apps, and entrees, all inspired by local chefs and our in-house mixologist. We truly are crafted to gather. Mix it up on the open concept ground floor tasting room or head to the Aviary, our rooftop patio, where you’ll be able to soak in the sights of beautiful Milwaukee.

Optional: Post-dinner cocktails at Bryants Cocktail Lounge

Open since 1938, Bryant’s is Milwaukee’s Oldest Cocktail Lounge. Indulge yourself with exotic lighting, plush velvet walls, and tunes from the vintage McIntosh-powered audio system. Cozy up in a booth while sipping on a classic signature cocktail and enjoying the finest service in Milwaukee.

Day 2 – Milwaukee to Wisconsin Dells

Cafe Benelux / Facebook

Breakfast at Café Benelux

Located in the heart of the vibrant Third Ward, Café Benelux celebrates the unique culture of Lowlands Europe with an award-winning Belgian bier selection, a full from-scratch menu, and one of Milwaukee’s most unique rooftop patios.

Enjoy a leisure stroll


  • Meander along the Milwaukee Riverwalk, a continuous 20 block path along the river tying together three distinct riverfront neighborhoods — the Historic Third Ward, Downtown, and Beerline B. It brings you to the doorstep of some of the city’s best restaurants, brewpubs, shops, and nightlife, and is also home to an outdoor art gallery called RiverSculpture. 
  • Explore the Lakefront area and take in the sights that include Veterans Park, Milwaukee Art Museum, the War Memorial, and Discovery World.
  • Explore the Historic Third Ward neighborhood, a revitalized warehouse district home to eclectic eateries, unique boutiques, and remarkable art. The neighborhood is home to the award-winning Third Ward Riverwalk and the nationally acclaimed Milwaukee Public Market.
Wisconsin Cheese Mart / Facebook

Visit Wisconsin Cheese Mart

The largest selection of Wisconsin Cheese in the World! Since 1938, we have offered the finest in Wisconsin Cheese.

Tour at Lakefront Brewery followed by lunch

Milwaukee’s own Lakefront Brewery started in 1987. Since then, the industrious and inventive craft brewery located on the Milwaukee River has become a city landmark and point of pride for locals. 

Tasting at Explorium Brewery Third Ward

We believe humans are endowed with an innate desire to learn about the world around us. We are certain that folks like Livingstone, Shackleton, and Earhart would have loved a place to gather around a fire, lift a glass in toast, and enjoy learning about each other’s discoveries. These were bold humans who lived in different eras and hailed from different lands, but all were endowed with an innate desire to explore and discover new people and places. The famous explorers of our past inspire us to travel to new places, meet new people, enjoy new customs, and try new flavors. Come gather around the fire, share your tales of travels near and far while exploring the flavors of hand-crafted beer and food inspired by cuisines from around the world with plenty of homegrown roots.

Depart Milwaukee Intermodal Station for Wisconsin Dells

Board the Empire Builder train to Wisconsin Dells

Welcome to Wisconsin Dells!

The VUE Boutique Hotel

Check in at The VUE Boutique Hotel

The Dells’ first Boutique Hotel located in Downtown Wisconsin Dells at the Historic Drinking Landing Dock. Located waterfront on the Dells Riverwalk.

Dinner at your leisure


Day 3 – Wisconsin Dells

Breakfast at your leisure


Wisconsin Dells Trolley Winery Tour

Embark on a relaxing Trolley Tour deep into wine country with a fun adventure you will never forget!

Your chauffeured Wine and gourmet lunch Trolley Tour activities include:

• A beautiful and scenic drive through the Wisconsin Woods to three wineries and great fun and music. A great way to reconnect with family and friends.
• Wine tastings at 3 local Wineries – Baraboo Bluff, Fawn Creek and Broken Bottle
• Case & multiple bottle discounts!
• Relaxing grounds and beautiful views

Carr Valley Cheese / Facebook

Free time to explore or rest


Tasting + dinner at Kilbourn Cork

The Kilbourn Cork features a variety of premium wines by the glass or bottle, specialty cocktails, craft beer, and appetizers. It’s time to “WINEDOWN” in the Dells.

Day 4 – Wisconsin Dells to La Crosse

Breakfast and free time to continue to explore downtown Wisconsin Dells

Lunch & Tasting at Latte Stone Brewery

Latte Stone is Wisconsin Dells’ newest taproom featuring in-house brews and other craft beers. Latte Stone Brewery also serves small shareable plates of Pacific Island cuisine using fresh ingredients.

Enjoy a Flight at Dells Distillery

This rustic country-themed restaurant and bar, located in Historic Downtown Wisconsin Dells, is family-friendly and offers a huge variety of unique. menu items (don’t miss the famous tater tots!). Dells Distillery’s house liquors include whiskey, vodka, brandy, rum, and gin.

Tour and a pint at Showboat Saloon

Showboat Saloon is one of the oldest bars and buildings in Wisconsin Dells with 24 revolving taps. 

Asgard Axe Throwing

Depart Wisconsin Dells Train Station for La Crosse

Board the Empire Builder train to La Crosse

Welcome to La Crosse!

Whether you are looking for a vacation or just a long weekend, the La Crosse Region offers something for everyone. Plan your stay nestled between towering bluffs and along the grand Mississippi River. With indoor and outdoor activitiesarts and culture, and a vast variety of places to eat and stay, you’re bound to enjoy the area from sunrise to sunset. Centrally located on I-90 between Minneapolis-St. Paul, Dubuque, Des Moines, Madison, Milwaukee, and Chicago, the La Crosse Region is an easily accessible destination that’s just a road trip away. Bring your family and friends for a weekend filled with a plethora of activities! 

Check in at Home2 Suites By Hilton La Crosse

Waterfront Restaurant / Facebook

Dinner at Waterfront Restaurant & Tavern

Day 5 – La Crosse

Breakfast at Fayze’s

Explore Riverside Park

The landmark park in La Crosse, Riverside Park is the center of an active community. At the confluence of three rivers, Riverside Park is designed for active lifestyles, and for those that want to just watch the river slowly pass by.

This park is the home of the La Crosse Queen. Visitors can take to the water and a Friday evening Pizza Cruise or a daily sight-seeing cruise on the La Crosse Queen.

At the north end of the park, guests enjoy strolling through the Riverside International Friendship Gardens.

Adjacent to the gardens is Riverside Museum and the offices for the La Crosse County Convention & Visitors Bureau. We invite visitors to take a step back in time and enjoy the history that makes our beautiful city unique!

Depending on the season, visitors may just be lucky enough to view one of the large steamboats that take port at the levee centered in the park. Make sure to have your cameras ready!

Lunch and tasting at La Crosse Distilling Co

Each of our handcrafted spirits is a unique expression of a particular place, a farmer’s passion and our careful work. Join us at our geothermal powered distillery and tasting room where Genuine Wisconsin Spirit is captured in every sip

Drinks at Bodega Brew Pub 

Spin the Craft Beer Wheel to choose your fate of over 400 beers.

Tasting at Turtle Stack Brewery

Craft Brewery and Tasting Room in La Crosse WI

Happy Hour and apps at Dublin Square

Lovechild / Facebook

Dinner at Lovechild

Lovechild ~100-seat restaurant and bar offering uncomplicated food with intriguing ingredients and big flavors – locally sourced and seasonally driven.

Day 6 – Depart La Crosse

Breakfast at The Breakfast Club & Pub

Explore Downtown La Crosse + lunch

Downtown La Crosse is home to some of the finest specialty shops in the region, including Generous Earth PotterySatori ArtsCrescent Jewelers, and Finnotte’s Nut & Chocolate Shop. Downtown also features Wisconsin’s largest antique mall, the Antique Center of La Crosse. With three stories and over 20,000 square feet of shopping space, this is an antiquer’s paradise! Be sure to check in with Downtown Main Street, Inc., a non-profit which has played an integral role in the revitalization of the downtown business district, for news and updates regarding sales and other related events in the downtown area.

Check out TJ’s Cheddarheads for all your Wisconsin and cheese-related souvenirs, including real cheese. 

Grab lunch downtown.

Depart from La Crosse Regional Airport (LSE)

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