Tour of Spookiness & Charm

After breakfast, hit the road for Galena. Start with a visit to Horseshoe Mound Preserve, where you can savor the view of rolling hills against the morning sun before the hustle and bustle begins. 

Those who wish to prolong the outdoorsy fun will want to check out Hoof it Goat Treks. You’ll get to hike through serene native prairies and forests, but with a delightfully unusual twist —you’ll be accompanied by goats!

From there it’s on to Main Street in downtown Galena, which boasts more than 125 shops and restaurants, from quaint boutiques to high-end stores and candy and ice cream shops. If shopping isn’t your cup of tea, partake in a Galena Trolley Tour, where you’ll learn about the area’s rich history and architecture (with plenty of photo ops, too).

A place to relax with a drink and a bite to eat should sound good by now. Swing by the Galena Cellars Tasting Room, where you can sip on a glass of wine and share delicious small plates with your group. Rumor has it that the tasting room is haunted, so keep your eyes peeled for any abnormal occurrences.

If you have a taste for the sweet and savory, wander into Bread & Vine Bakery. Grab a charcuterie board for the group, or sink your teeth into a flavorful macaron, chocolate tart, or giant eclair, and let the sugar rush ensue.

Get the adrenaline pumping after lunch with a ride on the Alpine Slide at Chestnut Mountain Resort. You’ll enjoy beautiful panoramic views as you take the chairlift up, then swiftly sled down a 2,000-foot track to the banks of the Mississippi.

No fall trip to Galena is complete without stopping by the Great American Popcorn Co. (a member of the Illinois Made program) to try the seasonal flavors. Their autumn blend is a mouthwatering combination of apple cinnamon, cinnamon toast, pumpkin spice, cherry and banana nut bread.

Before heading out for the evening, ask yourself, “What’s my beverage of choice?” The Galena area is home to several popular breweries and wineries, and spirit lovers can take a tour of Illinois Maker Blaum Bros. Distilling Co. before tasting the end product in the distillery bar.

Dinner won’t be an easy decision, but in truth, you can’t go wrong. Fritz & Frites is ideal if you fancy a European style, with French and German fare and a variety of wines in an elegant bistro setting. Or dine at Timmerman’s Supper Club on the bluffs in East Dubuque, where you’ll have an all-encompassing view of the Mississippi River. Fried Green Tomatoes, housed in a historic downtown Galena building, offers rustic Italian dishes and an intimate romantic atmosphere.

Now that you’ve had dinner, be prepared: the night is about to get spooky. The Haunted Galena Tour Company, which is said to offer the best ghost tour along the Mississippi, will lead you through the town’s streets by candlelight while a guide shares ghostly tales and eerie folklore.

If you prefer to make the chilling expedition to Galena’s historically haunted destinations by bus, go with Amelia's Galena Ghost Tours instead. Or skip the tour altogether and get tickets to a show at the P.T. Murphy Magic Theatre, where you’ll be entertained and mystified in a secluded 24-seat venue. 

When it’s time to wind down, you’ll have no shortage of choices. History enthusiasts are drawn to the DeSoto House Hotel, which is the state’s oldest operating hotel (it’s reportedly haunted, too). The Jail Hill Inn won a 2021 Tripadvisor Traveler’s Choice Award as one of the best bed and breakfast stays in the country. And at Eagle Ridge Resort & Spa, you’ll have access to first-class golf courses, a luxury spa, and 23 miles of hiking trails.