Twilight on the Mississippi - Historic Galena & Field of Dreams
September 1-4, 2026
Price Per Person
Single $1,025 / Double $825 / Triple $750 / Quad $625
Join Windmill Tours on a four-day, three-night heart of the Midwest experience. We will journey to one of America’s most beloved cinematic landmarks, spend an afternoon in historic Galena, IL, and enjoy a day long sightseeing cruise on the riverboat Twilight.
Please note: The itinerary may be subject to change based on factors outside of our control.
This trips featured attractions:
Morocco Supper Club
Supper Clubs can be found in the upper Midwest of the U.S. The supper club tradition is classic, elevated, and unforgettable.
Field of Dreams Movie Site
Located in Dyersville, Iowa where cinematic history and the spirit of baseball meet in the heart of Iowa. We will start our day with a conversation with a ghost player, followed by a tour of the farmhouse and then end the tour with a catered lunch in the barn. Feel the magic where “if you build it, they will come” first came to life.
Ulysses S Grant Home
Galena, Illinois residence, home of the Civil War hero and 18th U.S. President. We will tour this home which features original furnishings and hear fascinating stories from Grant’s life and legacy.
Historic Galena Illinois
Spend an afternoon and evening exploring the town of Galena. Galena is fully restored and looks much like it did in 1860, when Ulysses S. Grant moved here to help his father run Grant & Perkins Leather Store on Main Street. Some 85% of the downtown buildings were listed on the National Register of Historic Places. Galena’s shopping district is home to more than 200 unique stores and restaurants.
Riverboat Twilight
Step aboard for a one-day cruise on the Riverboat Twilight departing from Dubuque, Iowa. Cruise includes breakfast, a mid-morning snack, and full lunch. The tour heads through Lock and Dam #11 and takes in one of the most beautiful areas of the Mississippi River. If river conditions allow, we will dock and spend some time in the quaint little town or Guttenberg.
Timmerman’s Supper Club
Timmerman’s was founded in 1961 by Helen Timmerman. Timmerman’s is located above the Mississippi with stunning views.
Fenelon Place Elevator
Optional group walk to what has been called “the world’s steepest, shortest scenic railway with a view of three states at the top.” You will need $4 cash to ride this funicular railway which is 296 feet in length elevating passengers 189 feet from Fourth Street up to Fenelon Place.
What’s Included
Three nights hotel lodging in Dubuque, Iowa
All of the above attractions (Riverboat twilight tip not included)
Three breakfasts, two lunches, and two dinners
Water & snacks
Motorcoatch transportation (driver tip not included)
Prepare for your trip
Trip information will be sent approximately thirty days prior to the trip. In the meantime, if you have any questions, please contact Ruth at ruth@windmilltoursmi.com or by calling (231) 878-4961.