If you want to make the most of your time, go to a place that’s frozen in it! This fall, gather your favorite people and head to Galena Country, where history, scenic beauty, and seasonal festivities create the perfect backdrop for a group adventure. From colorful drives along rolling hills to cozy wineries, historic tours, and lively events, there’s no shortage of ways to celebrate the season together. Whether you’re catching up with old friends or making new memories, Galena Country sets the scene for an unforgettable fall getaway.

Three people standing next to a red trolley. A child is handing a ticket to an employee while their mother is waiting to board the trolley.

Day 1

First up is lunch with a view at The Summit Food & Spirits located at Chestnut Mountain Resort. Feast your eyes on incredible panoramas of the Mighty Mississippi while enjoying lunch, followed by check-in. Settle into your room before venturing downtown to Galena’s Historic Main Street, where you’ll be immersed in history on a Trolley Tour. After the tour, experience more than 125 boutiques, galleries, attractions, and eateries. Finish the day with a savory meal at Galena’s oldest supper club, the Log Cabin Steakhouse. Start the meal with an order of saganaki and finish with a flaming grasshopper! Then, cap off the evening with a nightcap at one of Galena’s many cozy bars, lounges, or local hangouts—find your perfect spot here.

Day 2

Enjoy breakfast at the resort or off-site at Big Bill's Sandwich Shop & Coffee Bar on Main Street. Next, head to the Ulysses S. Grant Home State Historic Site to tour the home of the United States' 18th President. Take note of the many original furnishings, still on display! Next, journey outside of town to Horseshoe Mound Preserve, where you can take in views of Galena and the rolling hills of the driftless region. Be ready to snap some photos of these unforgettable views! Looking for a fun activity to create a keepsake? Book a workshop at Board & Brush Creative Studio. For another original experience, take the group to a French Perfumes & Pastries workshop where you can enjoy handmade French pastries while creating a custom perfume. 

Grab a bite to eat at Green Street Tavern at Desoto House Hotel for lunch, followed by a ‘behind the scenes’ tour at Blaum Bros. Distilling Co. Make your way back to the resort to freshen up for fine dining at Timmerman’s Supper Club, a nostalgic restaurant perched along the bluffs of the Mississippi River backwaters.

Day 3

Finish breakfast at the resort with a relaxing chairlift ride overlooking the Mississippi River, then venture to town for shopping and wine tasting. Fuel up at Gobbies’s Sports Pub and Eatery for lunch before heading to Hoof it Goat Treks, where you’ll experience a peaceful hike through the forest while goats follow and play along the trails.

Everyone loves a good story, and here, one good story always leads to another. Make plans to experience Galena Country with the best of friends, because we may be old, but never the same old thing.