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Main street of Galena filled with people in halloween costumes.

Tour of Spookiness & Charm

Outdoors & Regional

3 Days 83 Miles

take a road trip so picturesque, it’s scary

Cozy sweaters & scary costumes. Pumpkins & jack-o-lanterns.

Every fall icon has its spooky counterpart. Take a trip that embraces both sides of Fall. Stroll through a Japanese Garden, then go on a walking ghost tour. Hike with a goat, then play detective in a murder mystery. 
Have breakfast at a B&B, then stay the night in a haunted hotel. 

Day 1:

Day 1: Rockford, Winnebago & Pecatonica

  • Exterior of Tinker Swiss Cottage Museum and Garden.

To begin your trip, grab a coffee and head out to Rock Cut State Park in Winnebago County. A brisk breeze, the smell of freshly fallen leaves, and wildlife viewing along the shores of the mighty Rock River will leave you feeling invigorated and ready to tackle the rest of the day.

A visit to the Anderson Japanese Gardens in Rockford will keep the nature theme going, albeit in a completely different setting. Here, every aspect of the Japanese-style landscape is a work of art, and you can even grab a bite at the on-site Fresco at the Gardens

However, if the previous stop triggered a craving for Japanese, have lunch at JMK Nipponwhere they’ll prepare a delectable dish right before your eyes. If a Scandinavian brunch is more your style, you’ll feel right at home at The Norwegian

Take a break from outdoor endeavors at the Tinker Swiss Cottage Museum and Gardenswhere you’ll experience striking Swiss architecture amid scenic surroundings during a 60 to 90-minute guided tour. Discover the cottage’s haunted side with a paranormal tour of the premises.

Next, bask in the sights and tastes of fall at Edwards Apple Orchard West. The kids will love the petting farm, and the whole crew will enjoy picking brightly-colored apples, pumpkins and raspberries. 

Wind down from the excitement of the day with a stroll on the Pecatonica Prairie Path and Bike Trail, which meanders through a mixture of picturesque farmland, woods, prairies, wetlands and urban areas between Freeport and Rockford.

When dinner time rolls around, stop into the cozy, rustic brewpub at Prairie Street Brewery, where you’ll find tasty house-brewed beers and a full food menu in a charming historic building along the Rock River.

Once it’s time to pack it in, grab a room at the Embassy Suites by Hilton Rockford Riverfront, a full-service hotel with an industrial chic, warehouse-style feel. Located next to the lovely Davis Park, you can open the curtains to gorgeous sunrise and sunset views along the Rock River.

Day 2:

Day 2: Galena

  • A couple walking across the main street in Galena with buildings either side

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.

Day 3:

Day 3: Galena

  • A person flies between between the tree tops

A breakfast of homestyle comfort food at Otto’s Place will be the perfect remedy for your end-of-trip blues.

Before heading home, the great outdoors beckon for a final taste of adventure. Rent an electric bike from Nuts Outdoors, then zoom down the Galena River trail on a sightseeing expedition. Next, soak in the spectacular views of Northwest Illinois one last time on a guided zipline journey with Long Hollow Canopy Tours.

Special note: The Halloween Parade & Festival, the 39th annual Galena Nouveau celebration and the Galena Country Fair are outstanding annual fall events that we recommend considering when you plan your trip.

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