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Shedd Aquarium
Looking down Main Street of Galena

A Romantic Galena Getaway

From Local Experts

3 Days 109 Miles


Apple River, East Dubuque, Elizabeth, Galena, Hanover, Stockton

From the local experts at Galena Country Tourism

Galena as a Romantic Getaway

Galena is lush with rolling hills, rich in history and loaded with incredible outdoor adventure, shopping, and dining. 

Only a few hours’ drive from bustling cities like Chicago, Des Moines, St. Louis, Milwaukee and the Twin Cities, Galena Country tops the list as a favorite romantic Midwest destination. The best thing about being where time forgot, is that you can lose all track of it.

Day 1:

Stockton, Elizabeth and Galena

  • Couple walking down street drinking coffee

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 E-Town Coffee Co., 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.

Continue on your romantic journey to Galena, to check into 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 businesses. The aroma of freshly popped gourmet popcorn, hand dipped chocolates and chargrilled burgers fill the air as you make your way in and out of exquisite boutique shops. 

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. In Galena Country, one good story always leads to another!

Day 2:

Galena, Hanover and East Dubuque

  • Timmermans supper club building at night
  • View from winery balcony

Enjoy a delightful, homemade breakfast at the guest house, followed with a morning paddle down the Galena River on kayaks rented from Nuts Outdoors. Break for lunch on Galena’s Historic Main Street at Green Street Tavern, located in the iconic DeSoto House Hotel. 

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!

Day 3:

Galena and Apple River

  • Thriving Thistle bistro interior looking at counter and cabinet
  • 2 people riding bikes on the Galena river trail

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 route along historic Stagecoach Trail and discover Thriving Thistle in Apple River, where you can fuel your vehicle and your body! Featuring healthy options for the road and dine-in, you’ll want to be sure to explore all of the offerings here!

Galena Country transports people to another time and place to enjoy one-of-a kind experiences and adventures. Some historic, some timeless and some brand-new. But always original.

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