Galena, Illinois: Charming Downtown and Top-Rated Wineries

Begin in charming downtown Galena, where fully 85 percent of the buildings are on the National Register of Historic Places. Here, you’ll find the historic DeSoto House Hotel, which is the state’s oldest operating hotel; Abraham Lincoln spoke from its balcony in 1856, and the hotel is so full of history that it’s said to be haunted. Visit the second-oldest post office in the USA as well as an impressive number of restaurants, antiques shops and cozy bed-and-breakfast inns. Antiques lovers will find plenty to browse, including reasonably priced old books and an eclectic assortment of fun, quirky items from interesting drinkware to colorful jewelry and children’s toys.

After a full day of shopping, enjoy tempting food in Galena’s many quaint restaurants, coffee shops and pubs. All tastes and styles can be found here, from casual fare in a relaxed atmosphere to high-end cuisine served in one-of-a-kind settings.  Another charming boutique hotel, The Irish Cottage, was built to look like an old-fashioned Irish inn. Be sure to visit Frank O’Dowd’s, the attached pub and restaurant.

Sample and shop for a variety of wineries in and around Galena. On Main Street, you’ll find Jamie’s Wine Studio, where you can browse hundreds of bottles in the wine shop or sit down for a relaxing glass at the wine bar. Also on Main Street, Massbach Ridge Winery has a tasting room, perfect for sampling delicious local wines.

At Rocky Waters Vineyard and Winery in nearby Hanover, two friendly dogs and the owners greet visitors. Taste a selection of their 14 wines in the tasting room, beautifully crafted of old wood. Located on a small lake, Rocky Waters also has a small cabin that visitors can rent for the night.

At Galena Cellars Vineyard, the vistas are as amazing as the wines. Enjoy reasonably priced tours and tastings of their wines, many of which have won awards.

All of the grapes used at the popular Massbach Ridge Winery are estate-grown, and tours are available from April through October, weather permitting. On a sunny day, you’ll enjoy a tour and expansive views of the seven-hectare property. Head inside to taste some of Massbach’s wines, more than 15 in all.

At Eagle Ridge Resort, choose from four championship courses. From the 14th hole, which is Eagle Ridge’s signature hole, golfers can see three states – Wisconsin, Iowa and, of course, Illinois. The course called “The General” is praised for its difficulty and beauty. Beyond golf, visitors can enjoy a kayaking, canoeing, biking or hiking trip or book a hot-air balloon ride. At the end of an active day, get pampered in the Stonedrift Spa. The resort offers a variety of accommodations, with everything from well-appointed rooms to villas.

For a slightly more rugged outdoors experience, visit Mississippi Palisades State Park, a National Natural Landmark at the nearby confluence of the Mississippi and Apple rivers in northwestern Illinois. Here, you can hike 25 kilometers of trails rich in Native American history, fish, picnic and enjoy the best of nature by staying overnight at one of the campsites.