Jo Daviess County & Galena Itinerary

Day One

Arrive at the Apple River Fort State Historic Site in historic Elizabeth, IL, the site of an important battle during the 1832 Black Hawk War. At the reconstructed fort, visitors can learn about life in Jo Daviess County during the early 1800s.

Indulge yourself in the local history of Elizabeth and Jo Daviess County at the Elizabeth History Museum, including lead mining and the history on the Apple River Fort. Stroll around the corner to the Chicago Great Western Railway Museum and discover many artifacts of northwestern Illinois railroads.

Spend your first night in Jo Daviess County at the Country Inn & Suites in Stockton. This award-winning property provides the amenities of home, along with the idyllic setting of the rural landscape of Jo Daviess County.

Day Two

Begin your day by heading south to Massbach Ridge Winery and tempt your taste buds with award-winning wine while enjoying the breathtaking views. Visit their tasting room and vineyard and explore the winery with a grand tour.

After a day of exploring, cap the evening off with a performance at Stockton’s Plum River Playhouse. With a wide variety of casts members from towns and cities near and far, this playhouse has churned out some incredible performances over the past several years. Whether you are seeking to tickle your funny bone or are in the mood for a serious drama, Plum River is sure to meet your expectations.

Southern Jo Daviess County

The day begins with an exploration that even Jacques Cousteau would envy. At Chestnut Mountain Resort, jump aboard Mississippi Explorer’s 1.5-hour cruise. You will experience the splendor of the Upper Mississippi River National Wildlife & Fish Refuge.

When the cruise ends, you will be transported to the top of Chestnut Mountain Resort for lunch at the Alpine Restaurant. Sitting high atop a wooded palisade overlooking the Mississippi River, you’ll enjoy a wide variety of American cuisine.

Spend your afternoon at Rocky Waters Vineyard/Winery in Hanover, where you’ll experience a spectacular view and taste wines from locally grown grapes. This vineyard has helped expand the grape-growing ventures in this county and has produced great wine for several years.

Your day ends at the Bernadine’s Stillman Inn, an historic bed & breakfast mansion in Galena.Check in and enjoy a themed dinner. Choose froma dinner theater or historical interactive dinner withthe original owners of the Stillman Inn. They alsodo themed lunches such as an afternoon tea withmusic or dining with a strolling minstrel.


Day One

For first-time visitors or even repeat guests, the crown jewel of Jo Daviess County – Galena – with a trolley tour is an absolute must. Travel throughthe historic town while viewing panoramas from the bluffs that rise high above the city.

Galena is rich in history, and especially when it comes to President Ulysses S. Grant. Discover the Ulysses S. Grant Home State Historic Site on the east bank of the Galena River. Before heading to historic Main Street, stop by The Belvedere, Galena’s largest mansion, or check out the Dowling House, Galena’s oldest house.

After taking in the incredibly gorgeous sights of Galena, it is time to now see the history by foot. Spend the rest of your day browsing Galena’s historic Main Street. The city’s 19th-century storefronts house more than 90 shops, offering a wide array of products to suit every interest.

The day comes to an end when you arrive at Eagle Ridge Resort & Spa just outside of Galena. This resort will meet all of your needs and definitely provides that “home away from home” experience. Enjoy the scenery of picturesque northwest Illinois at this top notch resort.

Day Two

History and architecture may still be on your minds, but there is more to Galena than what you first see. Head to Linmar Gardens and enjoy a guided tour of the breathtaking 3.5-acre gardens. From there, head to the west side of Galena to the

Ryan Mansion. There you can travel through time to 1882 and join the servants in their entertaining tours of Victorian Life. You will go even further in time when you join Annie Wiggins for tales of ghosts and folklore.

With the trip coming to the end seat yourself for a performance of “Mark Twain and the Laughing River” as Jim Post takes you back to the heyday of the Mississippi River. Through song and music, Mark Twain’s childhood comes back to life right in front of your eyes.

If you decide to stay one more night, try Timmerman’s Hotel & Resort. Located just 12 miles west of Galena in East Dubuque, they offer all the little comforts that make you feel at home.

No matter what your group’s interests, we are sure to find the right attractions, lodging or dining options to best suit your tour. Galena and Jo Daviess County provide bountiful options to make your next tour a success. For further assistance in planning your next tour, contact Celestino Ruffini, director of sales, at 888 4-Galena or

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