Friends of the 261 are offering you an opportunity to ride our vintage passenger cars from the Twin Cities to Milwaukee or Chicago. This trip will be on the route of behind Amtrak’s Empire Builder* along the Mississippi River. Watch nature along the Mississippi River as you pass through Red Wing and Winona. Look for bald eagles as we pass through Lake Pepin on our way through central Wisconsin.
Our fully restored passenger cars offer a memorable journey you’ll cherish for years to come! Meticulously refurbished with vintage charm and modern comfort, these classic railcars recall a golden era when traveling was half the vacation. As you settle into plush seating and take in the view through large picture windows, you’ll be transported not only across the landscape, but back in time to when elegance and adventure defined every mile.
- This trip will be featuring Friends of the 261 equipment, Caritas and Super Dome, these cars will start our journey by returning to the route the Milwaukee Road once traveled in regular service. These meticulously refurbished, fully restored cars recall the era when traveling was half the fun and offer a memorable journey, you’ll cherish for years to come!
While riding the rails, enjoy a delicious boxed lunch from Honey Baked Ham—knowing your journey helps support the restoration of Milwaukee Road Steam Locomotive 261.
These trips will have limited seating, all in premium class. With the recent reduction in air fares between the Twin Cities and Chicago, you may wish to fly one way and take the train the other.
Windy City – Twin Cities to Milwaukee & Chicago
Times
July 26, 2025
Minneapolis/St Paul to Chicago
Depart St. Paul Union Depot – 8:50 am
Arrive Milwaukee Amtrak Station – 2:57 pm
Arrive Chicago Union Station – 4:45 pm
This trip is one-way from Minneapolis/St. Paul to Chicago.
Food is included in the ticket price.
*Terms & Conditions Apply, This is NOT an excursion with the steam engine Milwaukee #261 or diesel Milw #32A