Apparently, Toscolano was the ancient "Benacum" for which the lake garda was named (Lake Garda was once called Lake Benaco). In light of the many archeological finds mainly unearthed where a sumptuous villa once stood, Toscolano Maderno was evidently a Roman settlement. From the 9th to the 14th century, Maderno on lake garda was the administrative center on the western shore and, subsequently, the summer residence of the Gonzaga dynasty, the princes of Mantua. The town later fell under the rule of Venice until 1797.

Along what is still known as the "Valley of the Paper-mills", the paper industry in Toscolano Maderno flourished as early as the 14th century. The paper was taken across Lake Garda to Verona, down the Adige River and up the Adriatic Sea to Venice. Due to the quality of its product, Toscolano on lake garda gradually became one of the most famous centers in Italy, almost equal to Fabriano. Gabriele di Pietro introduced the first print shops in Cecina and Messaga.
The Bible which Martin Luther used for his translation into German was printed there in 1487. Some of the most famous printers who worked in Toscolano during the first half of the 16th century were Paganino and Alessandro Paganini.