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Wisconsin Wine Tasting Train Rides: A Complete Guide

Published: May 25, 2025

By: Adam Burns

Wisconsin might not be the first state that comes to mind when one thinks of wine, but this scenic region is increasingly gaining recognition for its unique offerings in viticulture.

With its rich agricultural heritage, Wisconsin has given rise to a burgeoning wine industry. For those looking to immerse themselves in this region's vinicultural charm, wine tasting trains offer an exceptional experience that combines the pleasures of rail travel with the delights of wine tasting.

The concept of wine tasting trains has garnered attention for its ability to provide passengers with an immersive, leisurely journey through some of the state's most picturesque landscapes.

These wine trains are not just about sipping and savoring fine wines but also about enjoying the serene beauty of Wisconsin's countryside. The combination of rolling hills dotted with vineyards, lush green fields, and tranquil rivers creates a backdrop that is both enchanting and serene.

Experience the Rail Journey

One popular wine tasting train in Wisconsin is the "Winery Train Experience," which offers guests a delightful day excursion through the heart of Wisconsin's wine country. Departing from certain cities, such as Madison or Milwaukee, these trains typically travel leisurely to a selection of local wineries, enabling passengers to enjoy the full vine-to-glass experience.

The train itself is part of the charm. Often comprised of vintage railcars, guests can relax in comfortable seating while enjoying panoramic views. Some experiences include commentary from knowledgeable conductors who share insights on the local wine industry and the history of the railway, deepening the understanding of Wisconsin's unique wine story.

Onboard Wine Tastings

The key highlight of any wine tasting train journey is, of course, the opportunity to sample a variety of wines. Wisconsin hosts over 100 wineries, each offering its own distinctive blends and varietals. Onboard the wine train, tastings might include regional favorites like fruity reds, crisp whites, and even some lesser-known grape varieties that thrive in Wisconsin’s unique climate.

To enhance the tasting experience, trains often pair wines with gourmet snacks or small bites, providing the perfect complement to the wines being savored. Knowledgeable sommeliers or wine experts usually lead the tastings, offering insights into each wine's characteristics, vineyard origins, and the region's winemaking traditions.

Wisconsin Great Northern Railroad

The Wisconsin Great Northern Railroad offers scenic train rides in Northwestern Wisconsin, showcasing the beauty of the region's landscapes. Established in 1997, it operates on historic rail lines and provides various themed excursions, including dinner trains and family-friendly outings.

The railroad is known for its iconic vintage rail cars, offering a nostalgic journey back in time. Located in Trego, Wisconsin, it serves as a popular tourist attraction, combining the rich history of railroading with stunning natural vistas. The experience is both educational and entertaining, making it an excellent choice for history buffs and families looking to explore the area's heritage.

The railroad hosts 2-hour "Wine & Cheese" trains during select dates in the summer.  The excursions - which are hosted within the restored "Namekagon View", a Hi Level car that originally operated on the fabled Santa Fe's El Capitan.

Osceola & St. Croix Valley Railway

The Osceola & St. Croix Valley Railway is a heritage rail operation located in Osceola, Wisconsin. It is operated by the Minnesota Transportation Museum. The railway offers scenic train rides along the picturesque St. Croix River Valley, showcasing the natural beauty of the region.

Passengers can enjoy vintage train cars as they journey through lush landscapes, over historic bridges, and past charming small towns. The train excursions serve both as educational experiences, highlighting the area's railroad history, and as recreational outings for families and train enthusiasts. The railway runs from Osceola to Marine on St. Croix, providing a unique and nostalgic travel experience.

Among their many special events are wine tasting trains that sample local wineries in both Minnesota and Wisconsin.  The trip lasts about 1 1/2 hours.