Three original roller-coasters are still functioning to this day: the Jack Rabbit, Thunderbolt (originally named Pippin), and Racer. Another classic ride, the Old Mill, which was introduced in the early 1900s, survived a fire shortly after it's construction.

Kennywood, a National Historic Landmark, preserves several structures from its opening era, but two of the most significant "original" survivors are the Casino (now the Parkside Café) and the carousel pavilion (now a Johnny Rockets). The Casino, built in 1898, is a Shingle-style pavilion that originally served as a dining hall and social hub; despite its name, it never hosted gambling, as "casino" referred to a social "summer house" in Italian. The carousel pavilion, dating back to the turn of the century, still retains its historic architectural footprint even though it now houses a modern restaurant. Beyond buildings, the Old Mill (1901) is the park's oldest surviving ride, though it has been themed differently over the decades. In 2026, these structures form the "Historic District" of the park, standing as testament to the "Golden Age" of American amusement parks. Preservation efforts ensure that while the interior functions change to meet modern culinary needs, the exterior facades and structural skeletons remain consistent with their late-Victorian and Edwardian origins.