Make a Reservation

Galena Wine Country Getaway

Galena and the surrounding area boasts a surprisingly robust, yet somewhat undiscovered, Wine Country. From scenic road trips and intimate winery tours to award-winning wines and eclectic dining options, Galena stands apart in the Midwest as a top Wine Country Getaway destination.

No matter the time of year, you can create your own unique and fun wine country experience in Galena and Jo Daviess County by picking your favorites from our list of vineyards, tours, tastings, dining and lodging recommendations.

Galena Wine Country Getaway print-friendly PDF

Vineyards, Tastings and Tours

To reach the vineyards, you’ll meander along the scenic roads that thread through Jo Daviess County. Give in to the urge to linger along the way. Allow yourself to fully relax and soak in the sights of tree-dotted country roads, rolling pastures and panoramic vistas. This visual feast satisfies the soul even before you reach a vineyard. Once you arrive, fun and informative tours and tastings await.

Galena Cellars Vineyard & Winery (4746 N. Ford Rd., Galena) offers more than 40 distinct, award-winning and nationally-recognized varieties of wine. A tour of the vineyard reveals not only an impressive wine-making operation, but also a passion to identify the region’s signature grape through an experimental growing program. After a vineyard tour, kick back with a glass of wine on the veranda and enjoy the countryside vistas.

Massbach Ridge Vineyard & Winery (8837 S. Massbach Rd., Elizabeth) is about a 15-mile drive southeast of Galena through the hills of Jo Daviess County. The winery produces 18 varieties of wine from grapes primarily grown in the area. Tours are often given by family members and include expansive views and beautiful scenery.

Rocky Waters Vineyard & Winery (2003 W. Hanover Rd., Hanover) makes 14 wines from grapes grown on its 25-acre vineyard. Located about 17 miles south of Galena, the winery sits on a bluff overlooking the vineyard. A popular tasting choice is the Pear Tree Blush named for the vineyard’s pear tree, which has been dropping fruit on the ground for more than 75 years. The pears are never picked and instead allowed to fall to the ground saturating the soil and lending the nearby grapes a wonderful subtle pear flavor.

Fergedaboudit Vineyard & Winery (4595 Speer Rd., Hanover) is a hidden gem. With wonderful views and rustic Italian ambiance, this boutique winery specializes in dry, bold red wines crafted from grapes grown on the estate.

Tastings & Shopping

Practically frozen in time, Galena has nearly 1,000 buildings listed on the National Register of Historic Places. Its gently curving Main Street is lined by pristine examples of 19th century merchant storefronts. There is no argument that Galena’s historic Main Street is the real deal.

Plan to walk both sides of Main Street strolling in and out of art galleries, boutiques and specialty stores. Wine Lovers will delight to find two wine tasting rooms and a few wine shops on Galena’s Main Street.

Housed in a former granary building, Galena Cellars Tasting Room (515 S. Main St., Galena) is at the south end of Main Street. The winery, which has produced wine since the early 1970s, offers 40 varieties. Grab a glass of wine, peruse the gift shop and savor your selection on the shaded wine patio.

Housed in one of Galena's oldest commercial buildings, Galena River Wine & Cheese (420 S. Main St., Galena) boasts an impressive selection of wines from highly-regarded vineyards from around the world. Check out the extensive selection of cheeses, sausages and other specialty foods as well.

More tasting opportunities can be found at Jamie’s Wine Studio (209 S. Main St., Galena) and Massbach Ridge Tasting Room (117 N. Main St., Galena).


Galena boasts an extraordinary tapestry of restaurants from charming to fine dining. With nearly 30 choices there is no shortage of options.

Vinny Vanucchi’s ‘Little Italy’ (201 S. Main St., Galena) boasts a serious wine program with nearly 50 wines by the bottle. Many consider dining at Vinny Vanucchi's to be a Galena tradition - "No trip to Galena is complete without a meal at Vinny's!" With its multi-level dining room, signature house salad and garlic bread, and made-from-scratch Italian favorites, its easy to relax and savor an escape together.