The Best Small Town In Illinois For A 3-Day Weekend
Illinois is larger than many people realize. The Midwestern state is over three times the size of Denmark, five times the size of Belgium, and twice the size of Panama, leaving plenty of towns to explore beyond the usual Chicago visit. Trying to figure out where exactly to go for your next Illinois weekend away? Galena is a fantastic destination to have on your radar.
This small town, located in northwest Illinois, may have only 3,000 residents, but don’t let its population fool you. Galena’s Main Street has an incredible variety of local businesses, and nature preserves and ski slopes are just a short drive away. As a cherry on top, it was once home to a US President, giving the town a particularly fascinating history. Chances are, by the time you finish learning about this town, you will already be eyeing your calendar for your next three-day weekend!
Galena's Main Street

Galena’s Main Street is brimming with businesses, so much so that deciding where to begin can feel like a challenge! If you arrive in the morning, consider starting out at one of Main Street’s local coffee shops. The Wired Rabbit Coffee House is a wonderful option, opened in 2020, which is quickly developing a reputation for its delicious small-batch-roasted coffees and full-leaf teas. After grabbing your morning coffee, hit the nearby shops, such as Galena Apothecary, a cute boutique that sells globally-inspired personal care products and accessories. Beyond The Horizon is another great place on Main to grab a gift or souvenir, selling handcrafted jewelry, apparel, and decor.

Starting to get an appetite from all that shopping? Grab a bite at Durty Gurt’s, a family-owned burger joint established in 2007 that serves mouthwatering, hand-pattied burgers, melts, and sandwiches. A few of the unique, specialty burgers on the menu include The City Diner Burger, the Greek Town Burger, the Santa Fe Burger, and the Inferno Burger, giving you an idea of the innovative food that awaits.
Reserves and Skiing Resorts

Whether visiting during snowy weather or warm sunshine, Galena has the perfect outdoor activities. During the warmer weekends, you will love visiting Casper Bluff Land & Water Reserve, an 85-acre reserve along the Mississippi River bluffs. In addition to offering impressive views of the river, this area is also archaeologically significant. It is home to the Aiken Mound Group, a collection of 51 documented mounds that once served the Effigy Mound peoples before 1000 CE. Travelers can explore this reserve via a network of hiking trails during its open hours, between dawn and dusk.

During the winter, meanwhile, Galena proves to be the perfect destination for skiing and snowboarding. Chestnut Mountain Resort is just a 20-minute drive south of downtown Galena and is widely regarded as one of the Midwest’s premier ski destinations. This resort spans over 220 acres and features a 475-foot vertical drop, 19 ski and snowboard trails, and nine ski lifts, with trails ranging from beginner through advanced. In the summer, the resort’s alpine slide, bike park, and zipline course make it a great destination as well.
The Ulysses Grant Home

US History fanatics are in for a treat in Galena. The town boasts the former residence of the 18th US President, Ulysses S. Grant. This property was gifted to him in 1865 by local residents who welcomed him back as a hero after the Civil War. The brick house was built in 1860 and was beautifully furnished when he received it. After being elected president in 1868, Grant periodically visited the home throughout the remainder of his life.

In 1955, the home underwent a massive restoration, aiming to return it to its original 1860s appearance. Today, the Grant Home is listed on the National Register of Historic Places and is open for visits Wednesday through Sunday.
Historic Inns in Galena

To make your weekend away even more interesting, consider booking your stay at one of the town’s historic inns. Two stand out in particular: The Galena Inn and the Steamboat House. The Galena Inn, formerly known as the Victorian Mansion, dates back to 1856, when it was built by a wealthy banker and lead smelter in town. The estate saw many affluent and famous characters over the years, including President Grant, who delivered his departing speech from the inn’s very balcony! Today, the elegant, Victorian-era inn features eight authentically furnished guestrooms and offers luxurious amenities like English gardens, a hot tub, pillow-top mattresses, and more.
The Steamboat House is another historic option that should be on your radar. This mansion, also centrally located, was built in 1855 and showcases a beautiful Gothic Revival-style architecture. Covering 7,000 square feet, the home features five bedrooms, seven bathrooms, and seven fireplaces. Antique Czechoslovakian crystal chandeliers and 13-foot-tall ceilings on the first floor make it feel especially extravagant! Guests who stay here can enjoy private baths and fireplaces, a billiards room, and a formal dining room, along with other cozy touches throughout the property.
Galena is one of those towns that has an itinerary for every type of traveler. Prefer to spend your weekend outdoors? Nature reserves and mountain resorts abound. If your dream weekend is spent browsing shops and dining at local cafes, you can just as easily stay entertained downtown. The history lover’s itinerary, meanwhile, is just as extensive, featuring 19th-century landmarks and a presidential home. However you choose to spend it, do not be surprised if the weekend flies by!