9 Amazing Weekend Getaways In Illinois For 2026
Packed with small towns, Illinois is bursting with beautiful downtowns, quirky roadside attractions, natural escapes, and scenic river views that make every corner of the state perfect for a memorable weekend away. Visitors can take part in the unique Groundhog Days film-themed celebrations in Woodstock in winter or hike in a private wooded property in Galena in the company of adorable goats whom they can hand-feed and pet. The town of Casey is packed with gigantic surprises, many of which hold a proud position in the Guinness Book of World Records. Nature lovers will enjoy the gondola ride offering scenic views of the Mississippi River in Grafton, while the small town of Alton is home to the giant statue of the tallest person ever known. The following nine small towns are perfect for those planning a romantic retreat, a family-friendly getaway, or a solo reset.
Woodstock
Woodstock is a classic Midwestern town that has become increasingly iconic over the years, thanks in part to its appearance in the film Groundhog Day. The beautiful, historic square is the heart of the town, framed by brick buildings and the iconic Woodstock Opera House, hosting concerts, plays, and film screenings year-round. Seeking even more culture? Spend time perusing the shelves at Read Between the Lynes, a popular independent bookstore, or sip on coffee while enjoying some delicious chocolate at Ethereal Confections. Get outside and explore one of the many walking trails, or enjoy some disc golf at Emricson Park. Here for Groundhog Day? Not to worry, the town really leans into its namesake holiday, offering weekend-long activities based around the quirky tradition. If you're looking to live life like Bill Murray, the Cherry Tree Inn (the exact inn from the film) continues to offer stays in many historic and beautiful rooms.
Princeton
Princeton is a small town packed with Midwestern charm, offering a walkable historic downtown with several longstanding antique shops, like Eclectic Joy, and other local institutions. One significant cultural highlight in the town is the Owen Lovejoy Homestead, which offers insight into the town's abolitionist history and the Underground Railroad. In downtown, visitors can find daily entertainment at the historic Apollo Theater. During the summer, the town hosts the famed Festival 56, the largest theater festival in Illinois, with a lineup of musical, theatrical, and comedic performances. During October, the town hosts a living historical reenactment of a Civil War camp, Shadows of the Blue & Gray, complete with cannons, soldiers, and a visit from Abe Lincoln and Ulysses S. Grant. Just outside of town, travelers can drive to the Red Covered Bridge, a landmark dating as far back as 1863. Back in town, the Historic Knox Hotel offers Victorian-style rooms with modern-day comforts.
Galena
Galena may be small, but what it lacks in a large population it makes up for with its beautiful downtown area (one of the best in the United States), rolling hills, beautiful wineries, and historic riverfront. The town's walkable Main Street is lined with 19th-century brick storefronts, art galleries, restaurants, and boutiques, making it the perfect place to begin your weekend away. For a unique way to spend time here, join Hoof it + Sip it, a day spent sipping on wine and walking through the beautiful forest with a goat by your side. Those with young ones can still enjoy a goat walk with Hoof it, but with a root beer at their Goats + Floats walk instead. Back in downtown, live out your dream of becoming a woodworker at a spoon carving workshop, or take a ride aboard a historic trolley. Outside of exploring the historic downtown, those interested in learning even more about the area's historical significance can visit the Ulysses S. Grant Home and the Galena & U.S. Grant Museum. After a day spent exploring, rest your bones at the newly renovated Hotel Galena, a quaint red-bricked boutique hotel only a few blocks from Main Street.
Casey
Something big is happening in the small town of Casey, and no, it's not more Ulysses S. Grant impersonators. This quirky town happens to be home to some of the world's largest installations, many of which are featured in none other than the Guinness Book of World Records. Overall, the town is home to 25 unique larger-than-life items, including the world's largest mailbox, rocking chair, wind chime, and golf club — to name a few. Outside of spending time taking photos in this wonderland of gigantic objects, visitors can spend time perusing the aisles of antique shops like Deborah's Attic, enjoying a glass of wine or two at nearby Castle Finn Vineyard, or Cameo Vineyards. For a place to rest your head right in downtown, check out the historic Eighteen-Ninety Sleepover hotel.
Geneva
Once a Swedish settlement, this beautiful riverside town set along the scenic Fox River offers a perfect blend of history, natural beauty, and upscale appeal for the perfect getaway. Begin your weekend away in Geneva's downtown, where visitors will find Third Street lined with tons of unique shops, eateries, and galleries. Pop into the Little Traveler, with 36 rooms, it's the perfect place to find a fun trinket. Spend some time outside at Peck Farm Park, where you'll find acres of wide open space, interactive exhibits, a seasonal butterfly house, and a children's playground. For even more adventure, take a walk or bike ride along the Fox River Trail. Learn more about the town's history and enjoy interactive exhibits at the Geneva History Museum, or enjoy tranquility at the Fabyan Villa Museum & Japanese Garden. Enjoy a romantic overnight stay at the Oscar Swan Country Inn, the perfect base for your weekend away.
Ottawa
Known best as the gateway town to four of Illinois' major state parks, this small town is the perfect place for those seeking an outdoor getaway. Starved Rock State Park is the perfect spot to begin your weekend outside. Spend time exploring its sandstone canyons, miles of hiking trails, scenic overlooks, and beautiful waterfalls. Ottawa also sits at the intersection of the Illinois and Fox Rivers, making it the perfect place for kayaking, fishing, and boating. Back in town, its historic downtown is lined with quaint, brick 19th-century storefronts, and its historic Washington Square is the site where Abraham Lincoln and Stephen A. Douglas had their first senatorial debate. A short distance from the square sits Reddick Mansion, an opulent 19th-century estate where visitors can peruse the grounds, gardens, and tour the Italian-style architecture. Take a load off at the Fox River B&B, a historic Victorian-style farmhouse perfect for a romantic getaway.
Grafton
Along the Mississippi River, where Illinois meets Missouri, Grafton is a quaint river town perfect for outdoor enthusiasts. Although beautiful year-round, the town's beauty really shines during the autumn months, when the natural area is bursting with color. For something unique, visitors can hop on the Grafton SkyTour gondola, which offers sweeping views of the Mississippi and Illinois rivers. Continue the adventure at nearby Pere Marquette State Park, the perfect place for hiking and wildlife watching. Those looking for water activities can head to Grafton Harbor and rent a boat, or hop aboard a Hakuna Matata Boat tour to enjoy a scenic cruise. End the evening with a nightcap at Grafton Winery & Brewhaus, offering an array of wines and brews with a beautiful Mississippi River view. Those seeking accommodations with a view should look no further than Aerie's Resort, offering comfortable rooms overlooking the Mississippi.
Alton
Rich in history and perfectly positioned along the Mississippi River, Alton offers more than enough attractions to fill an engaging weekend. Not only was it once home to the world's tallest man (whose statue you can see just across from the Alton Museum of History and Art, but it's also home to an impressive collection of sites connected to Abraham Lincoln and the abolitionist movement.
Alton is also known as one of America's most haunted small towns. Visitors can join in on a spooky ghost tour or dive deep into the strange and mysterious at Troy Taylor's American Oddities Museum. End the night with a live performance at the Alton Little Theater, entertaining audiences since its opening in 1933. For a centrally located stay, the Beall Mansion, An Elegant Bed & Breakfast, provides a memorable overnight experience in a beautifully restored historic home.
Makanda
Looking for a town overflowing with character? Look no further than Makana, a hippie's paradise set at the edge of the Shawnee National Forest. In the heart of town, visitors will find the Makanda Boardwalk, a rustic strip of old railway buildings turned art galleries and craft shops, creating a one-of-a-kind atmosphere. Spend time sampling local wine at vineyards along the Shawnee Hills Wine Trail, or enjoy a day spent outside at the Giant City State Park, best known for its dramatic landscapes, waterfalls, and towering trees. Unwind at the Makana Inn & Cottages, a cozy lodging option surrounded by trees, and an ideal base for exploring southern Illinois.
Each of these Illinois towns offers its own distinct personality, making them ideal for a weekend filled with exploration, relaxation, and a touch of local flavor. Historic main streets, scenic riverfront views, expansive state parks, lively festivals, and one-of-a-kind attractions highlight just how diverse the state can be. No matter which town you choose, you’ll find plenty to see, do, and enjoy, perfect for a refreshing weekend escape.
