Welcome to Oregon, Illinois, a beautiful town with picturesque landscapes, fascinating history, and warm, friendly people. Looking for a peaceful bed and breakfast getaway? Oregon is the perfect destination. It is nestled along rocky cliffs, verdant forests, and the meandering Rock River. Oregon is at the crossroads of Illinois 64 and scenic route 2, only 27 miles south of Rockford and 90 miles west of Chicago. An exception small town, Oregon boasts: 4 State Parks and 10 City Parks An old fashioned paddleboat for lunch and dinner cruises An Historic Downtown and Unique Shopping Art Galleries and 3 Working Foundries Two bed and breakfast establishments Oregon has a rich art and cultural heritage that dates back to 1898, prestigious artists and writers located the Eagles' Nest Artist Colony here. The evidence of their presence remains in numerous statues located throughout the city. These can be viewed along Oregon's Sculpture Trail. One bed and breakfast is on the Nation Historic Register. Stop by for a tour. Festival enthusiasts remember Oregon for the famous Autumn on Parade event held the first weekend of October each year. It is one of the largest and finest small town festivals in Illinois featuring arts, crafts, and farmers market, auto show, riverfront events, and much more. Summertime fun includes The Fields Project and Arts Festival and The Ogle County Fair. Join Oregon's winter Candlelight Walk along with the opening of Sinnissippi Forest Christmas Tree Farm in bringing in the holiday season.