Galena Country Vacation Bucket List

Six unique experiences you don’t want to skip.

It’s pretty amazing here, with endless opportunities to explore – we’ve compiled a list of unique experiences to tackle on your next trip (or two….or three).

Take your vacation to new heights

Peacefully float above the rolling landscapes of Galena Country on a hot air balloon ride from Galena on The Fly. This incredible ride can carry up to 13 of your closest friends, flights last about an hour and end with a champagne toast and chocolates!

Long Hollow Canopy Tours will have you soaring through the treetops at speeds up to 40 mph at heights of up to 75 feet! This 2 1/2 hour thrilling journey begins with a UTV ride through the woods to the first platform, followed with a 140-foot sky bridge and a quick jump or rappel to the finish.

The perfect place for a picnic date with a view, Horseshoe Mound Preserve is located off of Blackjack road and boasts some of the best scenes of Galena. Use the viewing scopes to see geographical mounds of Illinois, Wisconsin, and Iowa, while enjoying the stone-henge style gathering space. A lovely location for a hike with the kids, pets or alone – be on the lookout for hidden treasures amongst the trees.

Epic Events

Full of infinite opportunities, from cemetery walks to hot air balloon races to incredible parades and magical holiday festivities. There’s always something to discover in Galena Country! Check the events calendar while planning your vacation to plan accordingly. While there’s fun to be had at every event, the following events made it to the bucket list.

Experience the 1860s through a Living History Encampment and Civil War Battle at Grant’s Home Front Reenactment on the banks of the Galena River. Free admission to those dressed in fully scout or military uniform.

The Galena Country Fair is one of the area’s most popular events, overflowing with original handmade arts and crafts, live entertainment and mouthwatering fair food. Indulge in the Gazebo Wine Garden featuring award-winning local wines and take advantage of the complimentary shuttle service available on both Saturday and Sunday.

Bringing in thousands of spectators, the Halloween Parade & Festival is something you don’t want to miss. Featuring spectacular floats, marching bands, costumed participants, prizes and treats, you can expect this to be an unforgettable weekend!

Romantic, nostalgic, and magical are just a few words to describe the Night of the Luminaria and Living Windows event. Stroll down the Helluva Half-Mile as more than 40 storefronts come to life with extraordinary holiday scenes. Thousands of twinkling, candle-lit luminaria brighten streets and walkways throughout the town, making for a lovely tour on foot, shuttle or via trolley.

All things Ulysses S. Grant

Stepping onto Galena’s Main Street is like something out of a movie. Looking much like it did when President Grant strolled the streets, it’s easy to see why Galena is often called the ‘City that’s Frozen in Time’. We’ve added a few historical ‘Grant features’ to the bucket list.

First up, the Ulysses S. Grant Home State Historic Site. The stunning, Italianate style home, was gifted to Grant upon his return home from the Civil War. With no detail overlooked, the home was fully furnished and proudly overlooks the city. In 1904, the Grant children donated the house to the city. It’s is open year-round for tours and features original furnishings.

Another must-see is the Elihu B. Washburne House State Historic Site, just a block away from Grant’s home. Washburne was a prominent attorney and later a popular U.S. Congressman, political advisor to Abraham Lincoln and U.S. Grant, and an ambassador to France. Visit the library where General Grant received the election night news via telegraph, that he was elected as President.

The DeSoto House Hotel, located in the heart of town was the center of Galena’s social and political activities. Being Illinois’ oldest operating hotel, it’s dripping with history. For a true ‘Grant experience’, you’ll want to book rooms 209 and 211, where he ran his presidential headquarters.

Take in the mighty Mississippi

Being the second longest river in the North American continent, the Mississippi River is a must-see while in Galena Country. Part of the driftless region, this captivating location is lush with rolling hills and breathtaking views for miles. Here are five amazing ways to experience the Mississippi River while on vacation.

Chestnut Mountain Resort is a premier destination to experience the river. Whether taking it all in from the dinner table, chair lift or river cruise, it’s an incredible year-round adventure.

For the perfect romantic getaway, stay and dine at the Goldmoor Inn. Take your dining experience to the next level and dine at the chef’s table, an intimate experience in the heart of the kitchen. Nestled along the bluffs of the river, this castle-like Inn offers an unforgettable, luxury experience.

Bring the dog, a picnic and explore sacred grounds overlooking the river at Casper Bluff Land & Water Reserve. Located just 10 minutes from downtown Galena, it’s an excellent location to unplug and reconnect with nature. Take some time to check out the 51+ Native American burial mounds, including one Thunderbird effigy.

Iconic Timmerman’s Supper Club offers another dining opportunity with a view. Perched along the bluffs of the backwaters, Timmerman’s offers a mouthwatering experience with no ‘bad seat’ in the house.

Just up the street from Timmerman’s, is Gramercy Park. A 10-acre park located on the bluffs in East Dubuque. This site is home to 26 ceremonial and burial mounds from the Hopewell Native American culture. Journey along the walking trails while the kids explore the playground, or relax and take it all in at the overlook pavilion.

Fascinating History

Galena, established in 1826 offers many awe-inspiring opportunities, here are a few favorite facts to share and explore.

The Dowling House, Galena’s oldest home, is really something to see. Nestled amongst the shopping and restaurants in downtown Galena, is a home built out of limestone, furnished with primitives and a collection of Galena pottery.

The oldest continually owned and operated Post Office in America is located on the corner of Green and Commerce St. in Galena. The building featuring Federal style architecture was constructed out of the best quality granite, shipped up the Mississippi from Nauvoo. An excellent location to send off your postcards and stop for a picture!

Another piece of treasured history is the Galena Fire Department, Illinois’ oldest fire department. Once comprised of five fire companies, Liberty house No. 1, located on Bench Street, is recognizable by its bell and can be seen from Main Street. The Galena Fire Department is now located at 101 S. Bench Street and has been a 100% volunteer department since inception in 1830.

The best in the U.S.

Galena Country is not only home to some ‘firsts’ and ‘oldest’ but is also the proud home to Jail Hill Inn. Rated the #1 B&B in the U.S. and #2 in the world by Trip Advisor, this romantic, luxury stay is one you don’t want to miss. Featuring a multiple-course breakfast that’s loaded with delicacy and indulgences, paired up with unique features in each room, the Jail Hill Inn has many ‘repeat offenders’, who come to experience the exclusivity of each room.

Adventure awaits, browse the digital travel guide and let the planning begin!