Vacation is all about relaxing and exploring a new city, and that often goes hand and hand with craft cocktails, local wine and beer, and cozy spots for a nightcap. During your stay, you’ll want to check out the best bars in Galena, IL, and taste your way down Main Street. If you’re a fan of a classic martini or old-fashioned or have a palate for wine, you’ll be satisfied with your choices in Galena, and you may have a lot more fun than expected! The hospitality professionals and the locals in Galena embody that “midwest-nice” mentality, and you’re bound to make a few new friends along the way.

After a drink or two at the best bars in Galena, you’ll be ready to relax back at our luxurious Bed and Breakfast—Jail Hill Inn. Each of our six spacious suites has a three-room layout: gorgeous seating areas with luxury couches and chairs, cozy pillows and throw blankets, and en suite high-end spa-bathrooms with deep soaking tubs or sizeable double steam showers. Join us in Galena and start planning your next exciting getaway today! 

Nightcaps & Happy Hours: Best Bars in Galena, IL

Heading out on the town is synonymous with vacation, and here are some of the best bars in Galena, IL, to let loose:

• Miss Kitty’s Grape Escape: Belly up to one of the best bars in Galena for a good time! A creative cocktail menu and fantastic wine selection only add to the friendly atmosphere at this local gathering space. Head here on the weekends for live music, open mics, and the Miss Kitty Quiz show on Sunday evenings.
• The Galena Tap House: One of the newest additions in town, this is one of the best bars in Galena to try local craft beers, only offering pours brewed within 200 miles of Galena. You’ll find delicious late-night fine dining options seven days a week and only a half-block from Jail Hill Inn!
• Galena Cellars Winery: This local tasting room covers three floors in a historic downtown brick building with flights of cold-weather varietal wines (grown just nearby), tasty share plates, and live music.
• Blaum Bros. Distillery: Just a few minutes from the downtown area of Galena, this local distillery is one of the best bars in Galena for your first cocktail and a tour of the distilling facility. Sink into one of the comfy leather couches with a creative cocktail mixed with one of their beautiful spirits made on-site.
• Galena Brewing Company: Head here for freshly brewed pints, festive events, hearty meals, and healthy fare. As a guest at our Galena Bed and Breakfast, you’ll be within a quick five-minute walk to this brewery. Take a tour, try a beer flight, and enjoy your time with friends.

• Gold Room Bar: This casual bar and grill is an excellent spot for a rousing game of shuffleboard, to watch the game on the big screens, and pick your favorite tunes on the jukebox.
• Embe Eatery and Lounge: For hearty cold and hot sandwiches, classic and creative martinis, and live entertainment, this local haunt is a great spot to relax. One of the best bars in Galena for a late-night drink!
• Champagne on Main: Add a little sparkle to your trip to Galena and head to this bubbly wine bar on Main Street. Aside from Champagne, they have a thoughtful selection of cocktails, bourbon flights, and a fantastic bottle selection.
• Bread and Vine: Don’t let the stunning display of French patisserie and desserts fool you—there’s also a lovely little bar top in the back of this Main Street cafe for a cozy cocktail. Pair that with their delicious sandwiches, fresh salads, and nightly specials.

The Best Happy Hour at our Galena Bed and Breakfast

One of the best perks at our Galena Bed and Breakfast is our afternoon wine and snacks board. Our guests always look forward to happy hour all day at our Inn! The custom-made board is delivered to your guest suite between 3 and 4 pm and comes with your choice bottle of white or red wine. The snack selection varies daily, but you can expect items like local cheeses from Galena River Wine & Cheese shop, house-roasted nuts, olives, creative crostinis, and skewers. Of course, no happy hour board is complete without a sweet treat, so you’ll always have home-baked cookies to follow up on your savory options.

Next up, head out on the town to these best bars in Galena for an evening full of music, fun, and adult beverages. Your unique guest suite will await your return. Slip into your robe, turn on your favorite Netflix show, and relax in style. And don’t worry, we’ve got breakfast covered in the morning. Book your next getaway to our Galena Bed and Breakfast today!