Of course, there are recognizable towns near Chicago that are on everyone’s radar—Galena, Illinois, and New Buffalo, Michigan, to name a few. These places attract all kinds of summer visitors due to their laid-back nature and charming small-town aura. However, we’re not in the business of gatekeeping, so if you’re looking for a weekend getaway that’s less crowded but still exudes a beautiful setting, may we suggest Oregon, Illinois?
Why Chicagoans are swapping big weekend crowds for Oregon, Illinois
Nestled along the Rock River in northern Illinois, Oregon, Illinois is one of the Midwest’s best-kept secrets, renowned for its rolling bluffs, galleries, museums, and public art installations. Here are some of the best things to do.
Castle Rock State Park
Located just a few miles south of Oregon, Castle Rock State Park is one of the most stunning parks to visit. The park features over six miles of hiking trails, ranging from short walks to moderate climbs through lush forests and along scenic bluffs.
During the summer months, White Pelican Canoe and Kayak offers kayaking and canoeing trips along the Rock River, which flows gently through the park.
Stronghold Castle
One of the most beautiful places to visit is Stronghold Castle. This Tudor-style palace, completed in 1931, features a whimsical watchtower as well as two natural bogs within its grounds. Since 1963, the castle has hosted an annual summer camp, mission groups, and various volunteer projects.
Lowden State Park
Visitors can expect dramatic cliff views, wooded ravines, and miles of hiking trails winding through Lowden State Park. However, the park’s main attraction is the Black Hawk Statue, a 50-foot concrete monolith created by Lorado Taft in 1911, which honors all Native American tribes of the region.

Sculpture Trail
This town is known as a cultural hub for art; it’s sort of a must to include some art-related activities in your itinerary. The Community Art Legacy is a contemporary project that began in 2004, introducing award-winning public sculptures throughout the town. Currently, 14 sculptures selected from an annual competition are available for public viewing year-round.
Conover Square
You must visit Conover Square if you’re in Oregon—the converted piano factory is located on North 3rd Street, and inside the expansive brick building, you’ll find two floors filled with antique stores, artisan boutiques, and studios offering the best vintage finds.