Start your day with a sumptuous 3-course gourmet breakfast at Jail Hill Inn. From there, head down to Galena’s Historic Main Street is just 1 block away. As you head south on Main Street, take in the scope of Galena’s extraordinary range of shops, historic architecture, and friendly small-town charm. Galena’s Main Street, nicknamed the “Helluva Half Mile,” is filled with over 100 different shops and boutiques. Some of our guests’ favorite stores to visit include The Towne Rebel, The Galena Canning Company, Galena Candle and Bath, Vignettes, Simply Elegant, Elle & Becks, Isabella’s, Poopsies, River Bend Gallery, and Images of Nature Gallery.
At some point while browsing shops, you’ll be ready for a small bite to eat. Stop in for a light-lunch and great coffee at Big Bill’s Café. After lunch, take a trolley tour. This one-hour tour is a great way to learn all about the historic significance of Galena, as well as see many of the most important sites in town. When you’re done, grab a cocktail or glass of wine at Galena River Wine & Cheese, Jamie’s Wine Studio, or the Green Street Tavern. Be sure to also enjoy Jail Hill’s Wine and Appetizer hour, which starts at 5pm everyday in our lobby. It’s the perfect way to unwind after a day of shopping and sightseeing. Cap off your evening with a delicious dinner at Fried Green Tomatoes.