Posted on October 21, 2025
Galena, Illinois is a historic town settled in a region known for its year-round beauty and renowned attractions. With vacation season always being around the corner, Galena with its hospitality and charming sights is fit for a perfect vineyard-centric getaway! With delicious local fare, pleasant stays, and fine selections of wine, there is much to enjoy. Come and enjoy our selection of Galena's wonderful locales in this Wine Weekend Getaway!
Stop 1 - Wine - Galena Cellars Vineyard & Winery
For our first pick, Galena Cellars Vineyard & Winery, held at the heart of the downtown, is set as a heart of the town's spirits! The homely interior on Main Street offers a consistent charm with an expansive collection for wine tastings and plenty of live music! For more adventurous outings, the Galena Cellars Vineyard welcomes all (including pets) with lodgings, heated igloos, weekly events, and vineyard tours! Wherever you choose, their stock of wine, cocktails, and hors d'oeuvres will keep the spirits high and guests satisfied. If you're planning on bringing along a larger group, check the Large Group Policy on their website before booking.
Galena Cellars Vineyard & Winery
111 N. Main St., Galena, IL 61036 (Downtown) | (815) 777-3330
4746 N. Ford Rd., Galena, IL 61075 (Vineyard) | (815) 777-3235 | Website
Stop 2 - Dinner - Vinny Vanucchi's 'Little Italy'
A perfect venue for a perfect homemade meal, Vinny Vanucchi's is host to great Italian cuisine fit for heartier appetites. After the first day of exploration, this restaurant holds many options from stuffed and baked pastas to sandwiches and seafood with a dedication to authenticity as the establishment always was. Vinny Vanucchi's is a venue best shared between friends and family with their historical group dinners, so check out their options for a shared table if you have a party reservation. Additionally, if you are feeling a casual wine experience, their selection offers options of a broad palette to sip from while enjoying a hearty meal including mixed drinks and beer with that!
Vinny Vanucchi's 'Little Italy'
201 S. Main Street, Galena, IL 61036 | (815) 777-8100 | Website
Stop 3 - Bed & Breakfast - Farmer's Guest House
With an evening stop, there is no better place to consider a proper Bed & Breakfast than Galena, IL with its charming selection of B&Bs across town and the surrounding region. However, for a good starter, the Farmer's Guest House with its tranquil privacy and hospitality that is well-written about the option. Their breakfast and spa services offered and renowned alongside their amenities such as the afternoon WineTime and, for the colder season, their Winter Weather Guarantee which makes this pick the best B&B in Galena! While staying the night, they also offer a selection of packages meant for occasions like a date night or a special celebration, adding yet another specialty of this place. For an affordable getaway and comfortable lodgings, the Farmer's Guest House is the place to stay!
Farmer's Guest House
334 Spring St., Galena, IL 61036 | (815) 777-3456 | Website
Stop 4 - Wine - Fergedaboudit Vineyard & Winery
Starting off the second day, there are many options to consider especially with what you'll be up to for the day! Starting off, we suggest checking out Fergedaboudit Vineyard & Winery where fun and wine waits! Wine tasting, vineyard tours, ticketed events, and live music are available throughout the week! Field made vintages and local blends, whether from the vineyard or from across the state, are prepared for your tasting pleasure either in their wine tasting room or on their casual patio! If you're looking for something entertaining, go on a day where there are any number of events at Fergedaboudit Vineyard & Winery; they will surely entertain!
Fergedaboudit Vineyard & Winery
4595 W. Speer Rd., Hanover, IL 61041 | (815) 591-2126 | Website
Stop 5 - Lunch - Woodbine Bend Golf Course and Restaurant
After your first stop at the vineyards, you're likely to be hungry which means you can have a drive down to the Woodbine Bend Golf Course and Restaurant for an exceptional lunch! Their lunch menu consists of a hearty selection of handhelds as well as a decent count of delicious appetizers, drink services, and wonderful customer service is set to impress! Whether you're there for a round or just for the meal, the exceptional views across the course are also sure to please! So stick around awhile and enjoy the views at this beautiful spot!
Woodbine Bend Golf Course and Restaurant
3500 E. Center Rd., Stockton, IL 61085 | (815) 858-3939 | Website
Stop 6 - Wine - Massbach Ridge Winery
In their over 22 years of experience, Massbach Ridge Winery has served good times and detailed experiences daily to countless guests much to their praise! A host is its share of seasonal events, music, and winery tours, the winery is a pleasant place for tasting and conversation after a long weekend of exploring local wine galleries. As a more casual spot with decades of experience surrounding its craft, Massbach Ridge Winery fits into a comfortable niche of housemade wines and a beautiful, well-staffed site to pair.
Massbach Ridge Winery
8837 S. Massbach Rd., Elizabeth, IL 61028 | (815) 291-6700 | Website
Stop 7 - Bed & Breakfast - Inn At Irish Hollow
For the last stop in this itinerary, an evening with the Inn At Irish Hollow closes out the weekend with a night at a rustic cottage and suite in the southern woods of Galena. As a select choice of B&B, the Inn At Irish Hollow offers delivered breakfast service, great rates and seasonal packages, expansive nature across the grounds, and plenty of additional enhancements to make the experience a once-in-a-lifetime evening! Regardless of the season, this B&B will always present its very best to all of its guests! With our last stop, we highly suggest you check out the impressive Irish Hollow Innkeeper's Blog for interesting insights into the hosts' work and interests!
Inn At Irish Hollow
2800 S. Irish Hollow Rd., Galena, IL 61036 | (815) 777-6000 | Website