A Romantic Galena Getaway for Couples

Explore along historic Hwy 20 and make a pit-stop in Stockton, to strike-a-pose in front of the vibrant murals that scale the downtown buildings. Slay that sweet tooth with a visit to Sweet Alice’s for bag-your-own-candy and hand-dipped salted caramels, made in-house.

Make your way to the Village of Elizabeth and fuel up at Terrapin Station Cafe, offering mouth-watering panini sandwiches, crisp salads, fresh coffee and a boutique wine room. Situated right in the heart of town, it’s a perfect location to stroll the town for a bit of shopping after lunch.

Arrive in Galena and check into your accommodations. Perched along the hillside, the Lamberson Guest House boasts some of Galena’s best views, not to mention a decadent breakfast and award-winning customer service.

Stepping onto Galena’s Main Street is like something out of a movie. Looking much like it did when President Grant strolled the streets, the buildings are now home to more than 125 independently owned shops, galleries, and restaurants. As you explore, you’ll catch the scent of gourmet popcorn, hand-dipped chocolates, and classic comfort food drifting through the air.

After dinner, be mystified by Galena's own Master Magician, P.T. Murphy! Murphy is known for his personable style, mischievous sense of humor, and sophisticated sleight of hand.

Start your morning with a homemade breakfast at the guest house before heading out for a paddle along the Galena River, with kayak rentals available seasonally through local outfitters, like Nuts Outdoors. Return to Main Street for lunch at Green Street Tavern, located inside the historic DeSoto House Hotel, one of Illinois’ oldest operating hotels.

The adventure doesn’t stop there! Discover the beauty of Blackjack Road and enjoy a few tastings at Fergedaboudit Vineyard & Winery in Hanover. Heading back towards Galena, you’ll want to be sure to stop at Chestnut Mountain Resort for a zoom down the alpine slide and a romantic snuggle on the chair lift. 

Spruce up for dinner and be ready to take in the majestic views while perched along the bluffs of the mighty Mississippi River at Timmerman’s Supper Club in East Dubuque. The perfect finish to any meal at Timmerman’s is with a hand-blended grasshopper. Be sure to save room!

Wake early and revel in a sunrise walk on the Galena River Trail, with a fresh brew from Kaladi’s Coffee Bar before checking out of your room. 

Take the scenic Stagecoach Trail toward Apple River and stop at Thriving Thistle, a modern convenience stop offering fresh, wholesome food options perfect for the road or a relaxed dine-in break.

A Destination Made for Two

Galena Country offers couples a romantic getaway defined by scenic beauty, preserved history, and experiences meant to be shared. Quiet moments, memorable meals, and thoughtfully paced adventures create the ideal setting for reconnecting and celebrating time together in one of the Midwest’s most distinctive destinations.